5-allylbenzo[d][1,3]dioxole (Safrole) by Asch

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Date

4 substances in Reaxys

2016-07-07 14h:36m:21s (EST)

1 substances in Reaxys

2016-07-07 14h:37m:14s (EST)

1. Query O

Search as: As drawn, No mixtures, No charges, No radicals 2. Query

(1. Query) AND itemno in (1)

1/69

2016-07-07 14:40:00

Reaxys ID 136380 View in Reaxys

1/1 CAS Registry Number: 94-59-7 Chemical Name: safrole; 1-allyl-3,4-methylenedioxybenzene Linear Structure Formula: CH2O2C6H3CH2CHCH2 Molecular Formula: C10H10O2 Molecular Weight: 162.188 Type of Substance: heterocyclic InChI Key: ZMQAAUBTXCXRIC-UHFFFAOYSA-N Note:

O O

Substance Label (48) Label References 1c

Ajay Kumar; Lokanatha Rai; Umesha; Tetrahedron; vol. 57; nb. 32; (2001); p. 6993 - 6996, View in Reaxys; Baricelli, Pablo J.; Rodriguez, Mariandry; Melean, Luis G.; Alonso, Maria Modroo; Borusiak, Margarita; Rosales, Merlin; Gonzalez, Beatriz; De Oliveira, Kelley C. B.; Gusevskaya, Elena V.; Dos Santos, Eduardo N.; Applied Catalysis A: General; vol. 490; (2015); p. 163 - 169, View in Reaxys; Baricelli, Pablo J.; Rodriguez, Mariandry; Melean, Luis G.; Alonso, Maria Modroo; Borusiak, Margarita; Rosales, Merlin; Gonzalez, Beatriz; De Oliveira, Kelley C. B.; Gusevskaya, Elena V.; Dos Santos, Eduardo N.; Applied Catalysis A: General; vol. 490; nb. 1; (2015); p. 163 - 169, View in Reaxys; Higman, Carolyn S.; De Araujo; Fogg, Deryn E.; Catalysis Science and Technology; vol. 6; nb. 7; (2016); p. 2077 - 2084, View in Reaxys

Bergami, Matteo; Protti, Stefano; Ravelli, Davide; Fagnoni, Maurizio; Advanced Synthesis and Catalysis; vol. 358; nb. 7; (2016); p. 1164 - 1172, View in Reaxys

Tsyganov, Dmitry V.; Krayushkin, Mikhail M.; Konyushkin, Leonid D.; Strelenko, Yuri A.; Semenova, Marina N.; Semenov, Victor V.; Journal of Natural Products; vol. 79; nb. 4; (2016); p. 923 - 928, View in Reaxys

Takasaki, Midori; Konoshima, Takao; Yasuda, Ichiro; Hamano, Tomoko; Tokuda, Harukuni; Biological and Pharmaceutical Bulletin; vol. 20; nb. 7; (1997); p. 776 - 780, View in Reaxys; Pinalli, Roberta; Barboza, Tahnee; Bianchi, Federica; Massera, Chiara; Ugozzoli, Franco; Dalcanale, Enrico; Supramolecular Chemistry; vol. 25; nb. 9-11; (2013); p. 682 - 687, View in Reaxys; Huang, Meiwei; Li, Lun; Zhao, ZhiGang; Chen, Qing-Yun; Guo, Yong; Synthesis (Germany); vol. 47; nb. 24; (2015); p. 3891 - 3900; Art.No: SS-2015-H0448-OP, View in Reaxys

Sharma, Pawan K.; Kumar, Surender; Kumar, Pawan; Nielsen, Poul; Tetrahedron Letters; vol. 48; nb. 49; (2007); p. 8704 - 8708, View in Reaxys; Sharma, Upendra K.; Sood, Swati; Sharma, Nandini; Rahi, Praveen; Kumar, Rakesh; Sinha, Arun K.; Gulati, Arvind; Medicinal Chemistry Research; vol. 22; nb. 11; (2013); p. 5129 - 5140, View in Reaxys; Reichl, Kyle D.; Dunn, Nicole L.; Fastuca, Nicholas J.; Radosevich, Alexander T.; Journal of the American Chemical Society; vol. 137; nb. 16; (2015); p. 5292 - 5295, View in Reaxys

Lee, Wei-Chih; Wang, Chun-Han; Lin, Yung-Huei; Shih, Wei-Chun; Ong, Tiow-Gan; Organic Letters; vol. 15; nb. 20; (2013); p. 5358 - 5361, View in Reaxys; Lee, Wei-Chih; Chen, Chien-Hung; Liu, Cheng-Yuan; Yu, Ming-Shiuan; Lin, Yung-Huei; Ong, Tiow-Gan; Chemical Communications; vol. 51; nb. 96; (2015); p. 17104 - 17107, View in Reaxys

Chen, Huoji; Yang, Wanfei; Wu, Wanqing; Jiang, Huanfeng; Organic and Biomolecular Chemistry; vol. 12; nb. 21; (2014); p. 3340 - 3343, View in Reaxys; Bagal, Dattatraya B.; Kachkovskyi, Georgiy; Knorn, Matthias; Rawner, Thomas; Bhanage, Bhalchandra M.; Reiser, Oliver; Angewandte Chemie - International Edition; vol. 54; nb. 24; (2015); p. 6999 - 7002; Angew. Chem.; vol. 127; nb. 24; (2015), View in Reaxys

Du, Shu-Shan; Yang, Kai; Wang, Cheng-Fang; You, Chun-Xue; Geng, Zhu-Feng; Guo, Shan-Shan; Deng, Zhi-Wei; Liu, Zhi-Long; Chemistry and Biodiversity; vol. 11; nb. 9; (2014); p. 1449 - 1456, View in Reaxys; Larsen, Casey R.; Paulson, Erik R.; Erdogan, Gulin; Grotjahn, Douglas B.; Synlett; vol. 26; nb. 17; (2015); p. 2462 - 2466; Art.No: ST-2015-B0231-L, View in Reaxys

Yang, Wanfei; Chen, Huoji; Li, Jianxiao; Li, Chunsheng; Wu, Wanqing; Jiang, Huanfeng; Chemical Communications; vol. 51; nb. 46; (2015); p. 9575 - 9578, View in Reaxys

4, 4h

Dian, Longyang; Wang, Sisi; Zhang-Negrerie, Daisy; Du, Yunfei; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3836 - 3842, View in Reaxys

Fang, Xianjie; Jackstell, Ralf; Beller, Matthias; Angewandte Chemie - International Edition; vol. 52; nb. 52; (2013); p. 14089 - 14093; Angew. Chem.; vol. 125; nb. 52; (2013); p. 14339 - 14343,5, View in Reaxys; Jiang, Huanfeng; Yang, Wanfei; Chen, Huoji; Li, Jianxiao; Wu, Wanqing; Chemical Communications; vol. 50; nb. 54; (2014); p. 7202 - 7204, View in Reaxys

Zheng, Jianxia; Sortais, Jean-Baptiste; Darcel, Christophe; ChemCatChem; vol. 6; nb. 3; (2014); p. 763 766, View in Reaxys

2/69

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G18

Li, Chen; Xu, Feng; Xie, De-Mei; Jing, Yu; Shang, Ming-Ying; Liu, Guang-Xue; Wang, Xuan; Cai, ShaoQing; Molecules; vol. 19; nb. 4; (2014); p. 4857 - 4879, View in Reaxys

Levin, Mark D.; Toste, F. Dean; Angewandte Chemie - International Edition; vol. 53; nb. 24; (2014); p. 6211 - 6215; Angew. Chem.; vol. 126; nb. 24; (2014); p. 6325 - 6329,5, View in Reaxys

Fernandes, Sylvia; Bhat, Sujata V.; Synthetic Communications; vol. 44; nb. 19; (2014); p. 2892 - 2898, View in Reaxys

Quteishat, Laith; Panossian, Armen; Le Bideau, Franck; Alsalim, Rana; Retailleau, Pascal; Troufflard, Claire; Rose, Eric; Dumas, Franoise; Journal of Organometallic Chemistry; vol. 776; (2014); p. 35 - 42, View in Reaxys

De Araujo Jr., Joao X.; Barreiro, Eliezer J.; Parente, Jose P.; Fraga, Carlos A. M.; Synthetic Communications; vol. 29; nb. 2; (1999); p. 263 - 273, View in Reaxys; Da Silva, Kezia Peixoto; De Souza, Ivone A.; De Faria, Antonio Rodolfo; Brondani, Dalci Jose; Leite, Ana Cristina Lima; Heterocyclic Communications; vol. 7; nb. 5; (2001); p. 445 - 448, View in Reaxys; Leite, Ana Cristina Lima; Da Silva, Kezia Peixoto; Brondani, Dalci Jose; Heterocyclic Communications; vol. 7; nb. 6; (2001); p. 555 - 558, View in Reaxys; Leite, Ana Cristina Lima; Peixoto Da Silva, Kezia; De Souza, Ivone A.; Magali De Araujo, Janete; Brondani, Dalci Jose; European Journal of Medicinal Chemistry; vol. 39; nb. 12; (2004); p. 1059 - 1065, View in Reaxys; Gonzalez-Serratos, Hugo; Chang, Ruzhang; Pereira, Edna F. R.; Castro, Newton G.; Aracava, Yasco; Melo, Paulo A.; Lima, Patricia C.; Fraga, Carlos A. M.; Barreiro, Eliezer J.; Albuquerque, Edson X.; Journal of Pharmacology and Experimental Therapeutics; vol. 299; nb. 2; (2001); p. 558 566, View in Reaxys; Moreira, Diogo Rodrigo de Magalhaes; Lima Leite, Ana Cristina; Pinheiro Ferreira, Paulo Michel; da Costa, Patricia Marcal; Costa Lotufo, Leticia Veras; de Moraes, Manoel Odorico; Brondani, Dalci Jose; do O Pessoa, Claudia; European Journal of Medicinal Chemistry; vol. 42; nb. 3; (2007); p. 351 - 357, View in Reaxys; Singh, Jasvinder; Sharma, Munisha; Kad, Goverdhan L.; Kaur, Jasamrit; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 46; nb. 12; (2007); p. 2053 - 2055, View in Reaxys; Wang, Li-Ying; Wang, Xiu-Hua; Tan, Jia-Lian; Xia, Shuai; Sun, Heng-Zhi; Shi, Jin-Wen; Jiang, Ming-Dong; Fang, Liang; Zuo, Hua; Dupati, Gautam; Jang, Kiwan; Shin, DongSoo; Bulletin of the Korean Chemical Society; vol. 33; nb. 11; (2012); p. 3571 - 3575, View in Reaxys; Hemelaere, Remy; Carreaux, Francois; Carboni, Bertrand; Journal of Organic Chemistry; vol. 78; nb. 13; (2013); p. 6786 - 6792, View in Reaxys; Babu, Meduri Suresh; Rai, Kuria Madhavu Lokanatha; Asian Journal of Chemistry; vol. 25; nb. 17; (2013); p. 9555 - 9557, View in Reaxys

Baader, Sabrina; Ohlmann, Dominik M.; Goossen, Lukas J.; Chemistry - A European Journal; vol. 19; nb. 30; (2013); p. 9807 - 9810, View in Reaxys

Li, Lun; Chen, Qing-Yun; Guo, Yong; Chemical Communications; vol. 49; nb. 78; (2013); p. 8764 - 8766, View in Reaxys

14h

Zhou, Lin; Liu, Xiaohua; Ji, Jie; Zhang, Yuheng; Hu, Xiaolei; Lin, Lili; Feng, Xiaoming; Journal of the American Chemical Society; vol. 134; nb. 41; (2012); p. 17023 - 17026,4, View in Reaxys; Zhou, Lin; Liu, Xiaohua; Ji, Jie; Zhang, Yuheng; Hu, Xiaolei; Lin, Lili; Feng, Xiaoming; Journal of the American Chemical Society; vol. 134; nb. 41; (2012); p. 17023 - 17026, View in Reaxys; Zhou, Lin; Liu, Xiaohua; Ji, Jie; Zhang, Yuheng; Hu, Xiaolei; Lin, Lili; Feng, Xiaoming; Journal of the American Chemical Society; vol. 134; nb. 49; (2012); p. 20208 - 20208, View in Reaxys

Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; WO2008/96998; (2008); (A1) English, View in Reaxys

Gaonkar; Lokanatha Rai; Prabhuswamy; Medicinal Chemistry Research; vol. 15; nb. 7-8; (2007); p. 407 417, View in Reaxys

11a

Kumar, Vinod; Sharma, Abhishek; Sharma, Meenakshi; Sharma, Upendra K.; Sinha, Arun K.; Tetrahedron; vol. 63; nb. 39; (2007); p. 9718 - 9723, View in Reaxys

Atir; Mallouk; Bougrin; Soufiaoui; Laghzizil; Synthetic Communications; vol. 36; nb. 1; (2006); p. 111 120, View in Reaxys

Yu, Zhengkun; Yan, Shenggang; Zhang, Guangtao; He, Wei; Wang, Liandi; Li, Yu; Zeng, Fanlong; Advanced Synthesis and Catalysis; vol. 348; nb. 1-2; (2006); p. 111 - 117, View in Reaxys

230

Waser, Jerome; Gaspar, Boris; Nambu, Hisanori; Carreira, Erick M.; Journal of the American Chemical Society; vol. 128; nb. 35; (2006); p. 11693 - 11712, View in Reaxys

T2/16,Ed.

Colladon, Marco; Scarso, Alessandro; Sgarbossa, Paolo; Michelin, Rino A.; Strukul, Giorgio; Journal of the American Chemical Society; vol. 128; nb. 43; (2006); p. 14006 - 14007, View in Reaxys

T. 2/5 Ed.

Cwik, Agnieszka; Hell, Zoltan; Fuchs, Aliz; Halmai, Dora; Tetrahedron Letters; vol. 46; nb. 38; (2005); p. 6563 - 6566, View in Reaxys

Protti, Stefano; Fagnoni, Maurizio; Albini, Angelo; Organic and Biomolecular Chemistry; vol. 3; nb. 15; (2005); p. 2868 - 2871, View in Reaxys

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Zacchino, Susana A.; Lopez, Silvia N.; Pezzenati, German D.; Furlan, Ricardo L.; Santecchia, Carina B.; Munoz, Lorena; Giannini, Fernando A.; Rodriguez, Ana M.; Enriz, Ricardo D.; Journal of Natural Products; vol. 62; nb. 10; (1999); p. 1353 - 1357, View in Reaxys; Chen, Yu-Chang; Chen, Jih-Jung; Chang, Ya-Ling; Teng, Che-Ming; Lin, Wei-Yu; Wu, Chin-Chung; Chen, Ih-Sheng; Planta Medica; vol. 70; nb. 2; (2004); p. 174 - 177, View in Reaxys

Janin, Yves L.; Decaudin, Didier; Monneret, Claude; Poupon, Marie-France; Tetrahedron; vol. 60; nb. 25; (2004); p. 5481 - 5485, View in Reaxys

Mata, Rachel; Morales, Iliana; Perez, Olga; Rivero-Cruz, Isabel; Acevedo, Laura; Enriquez-Mendoza, Isolda; Bye, Robert; Franzblau, Scott; Timmermann, Barbara; Journal of Natural Products; vol. 67; nb. 12; (2004); p. 1961 - 1968, View in Reaxys

Tsukada, Naofumi; Yagura, Yasushige; Sato, Tetsuo; Inoue, Yoshio; Synlett; nb. 10; (2003); p. 1431 1434, View in Reaxys

educt to 4a(vii)

Vishu Kumar; Mantelingu; Basappa; Rangappa; Heterocyclic Communications; vol. 9; nb. 2; (2003); p. 161 - 164, View in Reaxys

Datta, Swarup; Chang, Chia-Lung; Yeh, Kuo-Liang; Liu, Rai-Shung; Journal of the American Chemical Society; vol. 125; nb. 31; (2003); p. 9294 - 9295, View in Reaxys

1b, R1=R2=OCH2O-

Yuasa, Yoshifumi; Shibuya, Shiroshi; Yuasa, Yoko; Synthetic Communications; vol. 33; nb. 22; (2003); p. 3947 - 3952, View in Reaxys

Scott; Janusz; Perkins; Megharaj; Naidu; Kirkbride; Bulletin of Environmental Contamination and Toxicology; vol. 70; nb. 4; (2003); p. 824 - 831, View in Reaxys

Zappala, Maria; Grasso, Silvana; Micale, Nicola; Polimeni, Santina; De Micheli, Carlo; Synthetic Communications; vol. 32; nb. 4; (2002); p. 527 - 533, View in Reaxys

Lima, Patricia C.; Lima, Lidia M.; Da Silva, Kelli Cristine M.; Leda, Paulo Henrique O.; De Miranda, Ana Luisa P.; Fraga, Carlos A. M.; Barreiro, Eliezer J.; European Journal of Medicinal Chemistry; vol. 35; nb. 2; (2000); p. 187 - 203, View in Reaxys; Uchida, Mihoko; Nakajin, Shizuo; Toyoshima, Satoshi; Shinoda, Masato; Biological and Pharmaceutical Bulletin; vol. 19; nb. 4; (1996); p. 623 - 626, View in Reaxys

4, R2=3,4OCH2O

Dauban, Philippe; Ferry, Sandrine; Faure, Helene; Ruat, Martial; Dodd, Robert H.; Bioorganic and Medicinal Chemistry Letters; vol. 10; nb. 17; (2000); p. 2001 - 2004, View in Reaxys

Trost, Barry M.; Machacek, Michelle; Schnaderbeck, Matthew J.; Organic Letters; vol. 2; nb. 12; (2000); p. 1761 - 1764, View in Reaxys

SAF

Batiste-Alentorn; Xamena; Creus; Marcos; Environmental and Molecular Mutagenesis; vol. 24; nb. 2; (1994); p. 143 - 147, View in Reaxys; Nesslany, Fabrice; Marzin, Daniel; Mutagenesis; vol. 14; nb. 4; (1999); p. 403 - 410, View in Reaxys; Liu; Chen; Chi; Food and Chemical Toxicology; vol. 37; nb. 7; (1999); p. 697 - 702, View in Reaxys; Daimon, Hirohiko; Sawada, Shigeki; Asakura, Shoji; Sagami, Fumio; Teratogenesis Carcinogenesis and Mutagenesis; vol. 17; nb. 6; (1997); p. 327 - 337, View in Reaxys

26 (scheme 2)

Platonov; Proskuryakov; Antonio, Teka Zheremiash; Ryl'tsova; Platonova; Shvykin; Russian Journal of Applied Chemistry; vol. 72; nb. 2; (1999); p. 316 - 326, View in Reaxys

Brooks, Paige R.; Wirtz, Michael C.; Vetelino, Michael G.; Rescek, Diane M.; Woodworth, Graeme F.; Morgan, Bradley P.; Coe, Jotham W.; Journal of Organic Chemistry; vol. 64; nb. 26; (1999); p. 9719 - 9721, View in Reaxys

CXIX

Rudenko; Pragst; Russian Journal of Organic Chemistry; vol. 34; nb. 11; (1998); p. 1589 - 1626, View in Reaxys

Tayama, Sumiko; Mutation Research - Genetic Toxicology; vol. 368; nb. 3-4; (1996); p. 249 - 260, View in Reaxys

Sugimoto; Goto; Akao; Kiuchi; Kondo; Tsuda; Biological and Pharmaceutical Bulletin; vol. 18; nb. 4; (1995); p. 605 - 609, View in Reaxys

Rai, K. M. Lokanatha; Linganna, N.; Hassner, Alfred; Anjanamurthy, C.; Organic Preparations and Procedures International; vol. 24; nb. 1; (1992); p. 91 - 94, View in Reaxys

Related Structure (1) Related Structure References Zusammenfassende Darstellungen. Derivative (4) Comment (Derivative)

Guenther,E.; The Essential Oils, Bd. 2 <New York 1949> S. 526, View in Reaxys; Gildemeister,E.; Hoffmann,F.; Die aetherischen Oele, 4. Aufl., Bd. 3d <Berlin 1966> S. 449, View in Reaxys

References

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Bromderiv.: F: 169grad

Nigam; Ramaiah; Riechstoffe und Aromen; vol. 22; (1972); p. 378,388, View in Reaxys

Pentabromid: F: 169.5grad

Baslas; Baslas; Riechstoffe und Aromen; vol. 22; (1972); p. 155,156,158, View in Reaxys

Pentabromid: F: 169.5

Baslas; Baslas; Riechstoffe und Aromen; vol. 22; (1972); p. 200,202, View in Reaxys

Mischungen m. Terpineol: D

Koul; Nigam; Riechstoffe und Aromen; vol. 17; (1967); p. 269,270, View in Reaxys

Purification (2) Purification (method) separation with silica gel or dilute H2SO4 in CHCl3

References yakushijin k.; tohshima t.; kitagawa e.; et al.; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 1; (1984); p. 11 - 22, View in Reaxys Stahl; Trennheuser; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 293; (1960); p. 826,831, View in Reaxys; Furukawa; Nippon Kagaku Zasshi; vol. 80; (1959); p. 387,388, 389; Chem.Abstr.; nb. 13938; (1960), View in Reaxys

Melting Point (4) 1 of 4

Melting Point [°C]

Location

Page/Page column 1

Patent; FLEXITRAL, INC; WO2008/9926; (2008); (A2) English, View in Reaxys 2 of 4

Melting Point [°C]

Sanderson; Jones; Journal of the Society of Chemical Industry, London; vol. 42; (1923); p. 1 T, View in Reaxys; Waterman; Priester; Recueil des Travaux Chimiques des Pays-Bas; vol. 47; (1928); p. 849 Anm. 3; 1033, View in Reaxys; Naves; Ardizio; Bulletin de la Societe Chimique de France; (1957); p. 1053,1056, View in Reaxys; Priester; Recueil des Travaux Chimiques des Pays-Bas; vol. 57; (1938); p. 811,813, View in Reaxys 3 of 4

Melting Point [°C]

Solvent (Melting Point)

petroleum ether

Hillmer; Schorning; Zeitschrift fuer Physikalische Chemie, Abteilung A: Chemische Thermodynamik, Kinetik, Elektrochemie, Eigenschaftslehre; vol. 167; (1934); p. 407,415, View in Reaxys 4 of 4

Melting Point [°C]

11.2

Schiff; Chemische Berichte; vol. 17; (1884); p. 1937, View in Reaxys; Schimmel and Co.; Chem. Zentralbl.; vol. 73; nb. I; (1902); p. 1060, View in Reaxys; Flueckiger; Annalen der Physik (Weinheim, Germany); vol. 158; (1876); p. 248, View in Reaxys Boiling Point (18) Boiling Point [°C] Pressure (Boiling Point) [Torr]

References

120 - 130

10 - 15

Ou, Wenhua; Huang, Hong; Asian Journal of Chemistry; vol. 27; nb. 3; (2015); p. 1175 1176, View in Reaxys

94 - 94.5

Fujita; Yamashita; Bulletin of the Chemical Society of Japan; vol. 46; (1973); p. 3553, View in Reaxys

145

4.5

Nigam; Ramaiah; Riechstoffe und Aromen; vol. 22; (1972); p. 378,388, View in Reaxys

93 - 93.2

Baslas; Baslas; Riechstoffe und Aromen; vol. 22; (1972); p. 155,156,158, View in Reaxys

140

Ramaiah; Nigam; Riechstoffe und Aromen; vol. 22; (1972); p. 71,74, View in Reaxys; Narasimha; Nigam; Riechstoffe und Aromen; vol. 22; (1972); p. 231,236, View in Reaxys

104 - 105

Bochwic; Kapuscinski; Roczniki Chemii; vol. 39; (1965); p. 1251,1255; Chem.Abstr.; vol. 64; nb. 12656, View in Reaxys

62 - 63

0.2

Feugeas; Bulletin de la Societe Chimique de France; (1964); p. 1892, View in Reaxys

Biniecki; Krajewski; Acta Poloniae Pharmaceutica; vol. 17; (1960); p. 421,422, 423; Chem.Abstr.; vol. 55; nb. 14350; (1961), View in Reaxys

5/69

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69 - 70

1.5

Naves; Ardizio; Bulletin de la Societe Chimique de France; (1957); p. 1053,1056, View in Reaxys

235.9

760

Lecat,M.; Recueil des Travaux Chimiques des Pays-Bas; vol. 47; (1928); p. 15,16; Ann. Soc. scient. Bruxelles; vol. 47 I; (1927); p. 154, View in Reaxys

114 - 115

Kern; Shriner; Adams; Journal of the American Chemical Society; vol. 47; (1925); p. 1149, View in Reaxys

234.5

760

v. Rechenberg,C.; Einfache und fraktionierte Destillation, 2. Aufl. <Miltitz 1923>, S. 261, View in Reaxys; Brauer bei v. Rechenberg; Journal fuer Praktische Chemie (Leipzig); vol. <2> 101; (1921); p. 118, View in Reaxys

112.81

Brauer bei v. Rechenberg; Journal fuer Praktische Chemie (Leipzig); vol. <2> 101; (1921); p. 118, View in Reaxys

232 - 233 104

Woy; Archiv der Pharmazie (Weinheim, Germany); vol. 228; (1890); p. 40, View in Reaxys 11

231 - 233

Woy; Archiv der Pharmazie (Weinheim, Germany); vol. 228; (1890); p. 40, View in Reaxys Grimaux; Ruotte; Bulletin de la Societe Chimique de France; vol. <2> 11; (1869); p. 465; Justus Liebigs Annalen der Chemie; vol. 152; (1869); p. 91, View in Reaxys

162.2

100

v. Rechenberg,C.; Einfache und fraktionierte Destillation, 2. Aufl. <Miltitz 1923>, S. 261, View in Reaxys

106.4

v. Rechenberg,C.; Einfache und fraktionierte Destillation, 2. Aufl. <Miltitz 1923>, S. 261, View in Reaxys

Refractive Index (27) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.538

589

Fujita; Yamashita; Bulletin of the Chemical Society of Japan; vol. 46; (1973); p. 3553, View in Reaxys

1.536

589

Nigam; Ramaiah; Riechstoffe und Aromen; vol. 22; (1972); p. 378,388, View in Reaxys

1.53

Baslas; Baslas; Riechstoffe und Aromen; vol. 22; (1972); p. 155,156,158, View in Reaxys

1.536

589

Ramaiah; Nigam; Riechstoffe und Aromen; vol. 22; (1972); p. 71,74, View in Reaxys

1.5351

589

Narasimha; Nigam; Riechstoffe und Aromen; vol. 22; (1972); p. 231,236, View in Reaxys

1.536

589

1.5366

589

Messerschmidt; Arzneimittel-Forschung; vol. 18; nb. 12; (1968); p. 1618 - 1618, View in Reaxys

1.5385

589

Bochwic; Kapuscinski; Roczniki Chemii; vol. 39; (1965); p. 1251,1255; Chem.Abstr.; vol. 64; nb. 12656, View in Reaxys

1.5389

589

Feugeas; Bulletin de la Societe Chimique de France; (1964); p. 1892, View in Reaxys

1.5378

589

Biniecki; Krajewski; Acta Poloniae Pharmaceutica; vol. 17; (1960); p. 421,422, 423; Chem.Abstr.; vol. 55; nb. 14350; (1961), View in Reaxys

1.53191

656.3

Naves; Ardizio; Bulletin de la Societe Chimique de France; (1957); p. 1053,1056, View in Reaxys

1.53738

589

Naves; Ardizio; Bulletin de la Societe Chimique de France; (1957); p. 1053,1056, View in Reaxys

1.55064

486.1

Naves; Ardizio; Bulletin de la Societe Chimique de France; (1957); p. 1053,1056, View in Reaxys

1.5331

656.3

Waterman; Priester; Recueil des Travaux Chimiques des Pays-Bas; vol. 47; (1928); p. 1033, View in Reaxys

Baslas; Baslas; Riechstoffe und Aromen; vol. 22; (1972); p. 200,202, View in Reaxys

6/69

2016-07-07 14:40:00

1.5383

589

Waterman; Priester; Recueil des Travaux Chimiques des Pays-Bas; vol. 47; (1928); p. 1033, View in Reaxys

1.5518

486.1

Waterman; Priester; Recueil des Travaux Chimiques des Pays-Bas; vol. 47; (1928); p. 1033, View in Reaxys

1.5638

434

Waterman; Priester; Recueil des Travaux Chimiques des Pays-Bas; vol. 47; (1928); p. 1033, View in Reaxys

1.5381

589

Perkin; Trikojus; Journal of the Chemical Society; (1927); p. 1665, View in Reaxys

1.5339

656.3

Cotton; Mouton; Annales de Chimie (Cachan, France); vol. <8> 28; (1913); p. 215, View in Reaxys

1.539

589

Cotton; Mouton; Annales de Chimie (Cachan, France); vol. <8> 28; (1913); p. 215, View in Reaxys

1.5526

486.1

Cotton; Mouton; Annales de Chimie (Cachan, France); vol. <8> 28; (1913); p. 215, View in Reaxys

1.543

589

Abati; Gazzetta Chimica Italiana; vol. 40 II; (1910); p. 92, View in Reaxys

1.5392

589

17.5

Schimmel and Co.; Chem. Zentralbl.; vol. 73; nb. I; (1902); p. 1060, View in Reaxys

1.5369

656.3

Eijkman; Chemische Berichte; vol. 23; (1890); p. 862, View in Reaxys

1.542

589

Eijkman; Chemische Berichte; vol. 23; (1890); p. 862, View in Reaxys

1.5557

486.1

Eijkman; Chemische Berichte; vol. 23; (1890); p. 862, View in Reaxys

1.5679

434

Eijkman; Chemische Berichte; vol. 23; (1890); p. 862, View in Reaxys

Density (12) 1 of 12

Density [g·cm-3]

1.096

Measurement Temperature [°C]

Location

Page/Page column 1

Patent; FLEXITRAL, INC; WO2008/9926; (2008); (A2) English, View in Reaxys 2 of 12

Density [g·cm-3]

1.0329

Reference Temperature [°C]

Measurement Temperature [°C]

Nigam; Ramaiah; Riechstoffe und Aromen; vol. 22; (1972); p. 378,388, View in Reaxys 3 of 12

Density [g·cm-3]

1.0988

Reference Temperature [°C]

Measurement Temperature [°C]

Ramaiah; Nigam; Riechstoffe und Aromen; vol. 22; (1972); p. 71,74, View in Reaxys 4 of 12

Density [g·cm-3]

1.1

Reference Temperature [°C]

Measurement Temperature [°C]

Narasimha; Nigam; Riechstoffe und Aromen; vol. 22; (1972); p. 231,236, View in Reaxys 5 of 12

Density [g·cm-3]

1.104

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Baslas; Baslas; Riechstoffe und Aromen; vol. 22; (1972); p. 200,202, View in Reaxys; Baslas; Baslas; Riechstoffe und Aromen; vol. 22; (1972); p. 155,156,158, View in Reaxys 6 of 12

Density [g·cm-3]

1.103

Measurement Temperature [°C]

Koul; Nigam; Riechstoffe und Aromen; vol. 17; (1967); p. 269,270, View in Reaxys 7 of 12

Density [g·cm-3]

1.0993

Reference Temperature [°C]

Measurement Temperature [°C]

Naves; Ardizio; Bulletin de la Societe Chimique de France; (1957); p. 1053,1056, View in Reaxys 8 of 12

Density [g·cm-3]

1.1

Reference Temperature [°C]

Measurement Temperature [°C]

Waterman; Priester; Recueil des Travaux Chimiques des Pays-Bas; vol. 47; (1928); p. 1033, View in Reaxys 9 of 12

Density [g·cm-3]

1.095

Reference Temperature [°C]

Measurement Temperature [°C]

Dunstan; Hilditch; Zeitschrift fuer Elektrochemie und Angewandte Physikalische Chemie; vol. 18; (1912); p. 187,884, View in Reaxys 10 of 12

Density [g·cm-3]

1.106

Measurement Temperature [°C]

Schimmel and Co.; Chem. Zentralbl.; vol. 73; nb. I; (1902); p. 1060, View in Reaxys 11 of 12

Density [g·cm-3]

1.11

Measurement Temperature [°C]

Eijkman; Chemische Berichte; vol. 23; (1890); p. 862, View in Reaxys 12 of 12

Density [g·cm-3]

1.114

Measurement Temperature [°C]

Grimaux; Ruotte; Bulletin de la Societe Chimique de France; vol. <2> 11; (1869); p. 465; Justus Liebigs Annalen der Chemie; vol. 152; (1869); p. 91, View in Reaxys Association (MCS) (3) 1 of 3

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

CCl4

Partner (Association (MCS))

chloranil

Yan, Bao-Zhen; Zhang, Zhao-Guo; Yuan, Han-Cheng; Wang, Long-Cheng; Xu, Jian-Hua; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 12; (1994); p. 2545 - 2550, View in Reaxys 2 of 3

Description (Association UV/VIS spectrum of the complex (MCS))

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Solvent (Association (MCS))

CCl4

Partner (Association (MCS))

chloranil

Description (Association NMR spectrum of the complex (MCS)) Solvent (Association (MCS))

benzene-d6

Partner (Association (MCS))

chloranil

Azeotropes

benzyl alcohol

Brauer; Ber. Schimmel; (1929); p. 151,156, View in Reaxys 2 of 21

Temperature (Azeotropes (MCS)) [°C]

190.1

Pressure (Azeotropes (MCS)) [Torr]

760

Azeotropes

glycol

Meerwein; Journal fuer Praktische Chemie (Leipzig); vol. <2> 113; (1926); p. 11,25, View in Reaxys 3 of 21

Temperature (Azeotropes (MCS)) [°C]

99.7

Pressure (Azeotropes (MCS)) [Torr]

760

Azeotropes

water

Meerwein; Journal fuer Praktische Chemie (Leipzig); vol. <2> 113; (1926); p. 11,25, View in Reaxys 4 of 21

Temperature (Azeotropes (MCS)) [°C]

208.8

Pressure (Azeotropes (MCS)) [Torr]

760

Azeotropes

acetamide

Meerwein; Journal fuer Praktische Chemie (Leipzig); vol. <2> 113; (1926); p. 11,25, View in Reaxys 5 of 21

Temperature (Azeotropes (MCS)) [°C]

231.2

Pressure (Azeotropes (MCS)) [Torr]

760

Azeotropes

glycerol

Meerwein; Journal fuer Praktische Chemie (Leipzig); vol. <2> 113; (1926); p. 11,25, View in Reaxys 6 of 21

Temperature (Azeotropes (MCS)) [°C]

213

Pressure (Azeotropes (MCS)) [Torr]

760

Azeotropes

propionamide

Meerwein; Journal fuer Praktische Chemie (Leipzig); vol. <2> 113; (1926); p. 11,25, View in Reaxys 7 of 21

Temperature (Azeotropes (MCS)) [°C]

232.4

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Pressure (Azeotropes (MCS)) [Torr]

760

Azeotropes

o-phenetidine

Meerwein; Journal fuer Praktische Chemie (Leipzig); vol. <2> 113; (1926); p. 11,25, View in Reaxys 8 of 21

Temperature (Azeotropes (MCS)) [°C]

234.8

Pressure (Azeotropes (MCS)) [Torr]

760

Azeotropes

benzoic acid

Meerwein; Journal fuer Praktische Chemie (Leipzig); vol. <2> 113; (1926); p. 11,25, View in Reaxys 9 of 21

Temperature (Azeotropes (MCS)) [°C]

232.5

Pressure (Azeotropes (MCS)) [Torr]

760

Azeotropes

caprylic acid

Meerwein; Journal fuer Praktische Chemie (Leipzig); vol. <2> 113; (1926); p. 11,25, View in Reaxys 10 of 21

Temperature (Azeotropes (MCS)) [°C]

233.6

Pressure (Azeotropes (MCS)) [Torr]

760

Azeotropes

pyrocatechol

Meerwein; Journal fuer Praktische Chemie (Leipzig); vol. <2> 113; (1926); p. 11,25, View in Reaxys 11 of 21

Temperature (Azeotropes (MCS)) [°C]

234.5

Pressure (Azeotropes (MCS)) [Torr]

760

Azeotropes

4-nitro-toluene

Meerwein; Journal fuer Praktische Chemie (Leipzig); vol. <2> 113; (1926); p. 11,25, View in Reaxys 12 of 21

Temperature (Azeotropes (MCS)) [°C]

233.8

Pressure (Azeotropes (MCS)) [Torr]

760

Azeotropes

ethyl salicylate

Meerwein; Journal fuer Praktische Chemie (Leipzig); vol. <2> 113; (1926); p. 11,25, View in Reaxys 13 of 21

Azeotropes

quinoline

Lecat,M.; Tables azeotropiques, 2. Aufl. <Bruessel 1949>, View in Reaxys 14 of 21

Azeotropes

heptanoic acid

Lecat,M.; Tables azeotropiques, 2. Aufl. <Bruessel 1949>, View in Reaxys 15 of 21

Azeotropes

levulinic acid

Lecat,M.; Tables azeotropiques, 2. Aufl. <Bruessel 1949>, View in Reaxys 16 of 21

Azeotropes

4-bromo-phenetole

Lecat,M.; Tables azeotropiques, 2. Aufl. <Bruessel 1949>, View in Reaxys 17 of 21

Azeotropes

diethylene glycol

Lecat,M.; Tables azeotropiques, 2. Aufl. <Bruessel 1949>, View in Reaxys 18 of 21

Azeotropes

3-phenyl-propan-1-ol

Lecat,M.; Tables azeotropiques, 2. Aufl. <Bruessel 1949>, View in Reaxys 19 of 21

Azeotropes

#O!-methyl-triethylene glycol

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Lecat,M.; Tables azeotropiques, 2. Aufl. <Bruessel 1949>, View in Reaxys 20 of 21

Azeotropes

bis-<2-hydroxy-propyl>-ether

Lecat,M.; Tables azeotropiques, 2. Aufl. <Bruessel 1949>, View in Reaxys 21 of 21

Azeotropes

carbonic acid diisopentyl ether

Lecat,M.; Tables azeotropiques, 2. Aufl. <Bruessel 1949>, View in Reaxys Chromatographic Data (3) Chromatographic Location data GC (Gas chromatography)

HPLC (High performance liquid chromatography)

References Parise-Filho, Roberto; Pasqualoto, Kerly Fernanda Mesquita; Magri, Fatima Maria Motter; Ferreira, Adilson Kleber; Da Silva, Barbara Athayde Vaz Galvao; Damiao, Mariana Celestina Frojuello Costa Bernstorff; Tavares, Mauricio Temotheo; Azevedo, Ricardo Alexandre; Auada, Aline Vivian Vatti; Polli, Michelle Carneiro; Brandt, Carlos Alberto; Archiv der Pharmazie; vol. 345; nb. 12; (2012); p. 934 - 944, View in Reaxys; Leporatti, Maria Lucia; Pintore, Giorgio; Foddai, Marzia; Chessa, Mario; Piana, Andrea; Petretto, Giacomo Luigi; Masia, Maria Dolores; Mangano, Giuseppe; Nicoletti, Marcello; Natural Product Research; vol. 28; nb. 5; (2014); p. 294 - 300, View in Reaxys; Li, Chen; Xu, Feng; Xie, De-Mei; Jing, Yu; Shang, Ming-Ying; Liu, Guang-Xue; Wang, Xuan; Cai, Shao-Qing; Molecules; vol. 19; nb. 4; (2014); p. 4857 - 4879, View in Reaxys; Linde, Johan; Combrinck, Sandra; Van Vuuren, Sandy; Van Rooy, Jacques; Ludwiczuk, Agnieszka; Mokgalaka, Ntebogeng; Phytochemistry Letters; vol. 16; (2016); p. 61 - 69, View in Reaxys

supporting information

Bhattacherjee, Abhishek; Datta, Abhijit; Ghosh, Tanushree; Sil, Rajarshi; Natural Product Research; vol. 28; nb. 23; (2014); p. 2199 - 2202, View in Reaxys

GC (Gas chroma- supporting infortography) mation

Wang, Guan-Jie; Qi, Mei-Ling; Chinese Chemical Letters; vol. 24; nb. 6; (2013); p. 542 - 544, View in Reaxys

Crystal Property Description (5) Colour & Other Location Properties

References

colourless

Ou, Wenhua; Huang, Hong; Asian Journal of Chemistry; vol. 27; nb. 3; (2015); p. 1175 1176, View in Reaxys; Du, Shu-Shan; Yang, Kai; Wang, Cheng-Fang; You, Chun-Xue; Geng, Zhu-Feng; Guo, Shan-Shan; Deng, Zhi-Wei; Liu, Zhi-Long; Chemistry and Biodiversity; vol. 11; nb. 9; (2014); p. 1449 - 1456, View in Reaxys

colourless

supporting information

Reichl, Kyle D.; Dunn, Nicole L.; Fastuca, Nicholas J.; Radosevich, Alexander T.; Journal of the American Chemical Society; vol. 137; nb. 16; (2015); p. 5292 - 5295, View in Reaxys

yellow

supporting information

Levin, Mark D.; Toste, F. Dean; Angewandte Chemie - International Edition; vol. 53; nb. 24; (2014); p. 6211 - 6215; Angew. Chem.; vol. 126; nb. 24; (2014); p. 6325 - 6329,5, View in Reaxys

cream - yellow colorless - yellow

Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; WO2008/96998; (2008); (A1) English, View in Reaxys Page/Page column 1

Dynamic Viscosity (1) Dynamic Viscosi- Temperature (Dyty [P] namic Viscosity) [°C] 0.0229

Patent; FLEXITRAL, INC; WO2008/9926; (2008); (A2) English, View in Reaxys

References

Dunstan; Hilditch; Zeitschrift fuer Elektrochemie und Angewandte Physikalische Chemie; vol. 18; (1912); p. 187,884, View in Reaxys

Electrochemical Characteristics (5) 1 of 5

Description (Electrochemical Characteristics)

cyclovoltammetry

Solvent (Electrochemical Characteristics)

acetonitrile

Comment (Electrochem- Saturated silver chloride electrode; potential diagram; lithium perchlorate ical Characteristics)

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Wang, Lai-Hao; Chang, Chia-Ling; Hu, Yi-Chun; Croatica Chemica Acta; vol. 88; nb. 1; (2015); p. 35 - 42, View in Reaxys 2 of 5

Description (Electrochemical Characteristics)

cyclovoltammetry

Solvent (Electrochemical Characteristics)

acetonitrile

Comment (Electrochem- Saturated silver chloride electrode; potential diagram; tetrabutylammonium perchlorate ical Characteristics) Wang, Lai-Hao; Chang, Chia-Ling; Hu, Yi-Chun; Croatica Chemica Acta; vol. 88; nb. 1; (2015); p. 35 - 42, View in Reaxys 3 of 5

Description (Electrochemical Characteristics)

cyclovoltammetry

Solvent (Electrochemical Characteristics)

acetonitrile

Comment (Electrochem- Saturated silver chloride electrode; potential diagram; tetraethylammonium perchlorate ical Characteristics) Wang, Lai-Hao; Chang, Chia-Ling; Hu, Yi-Chun; Croatica Chemica Acta; vol. 88; nb. 1; (2015); p. 35 - 42, View in Reaxys 4 of 5

Description (Electrochemical Characteristics)

oxidation potential

Solvent (Electrochemical Characteristics)

acetonitrile; various solvent(s)

Temperature (Electrochemical Characteristics) [°C]

Rudenko; Pragst; Russian Journal of Organic Chemistry; vol. 34; nb. 11; (1998); p. 1589 - 1626, View in Reaxys 5 of 5

Description (Electrochemical Characteristics)

redox potential

Solvent (Electrochemical Characteristics)

acetonitrile

Comment (Electrochem- 1.4 V; Product: /BRN= 1577733/. Method: cyclovoltammetry. Description: Pt electrode vs. ical Characteristics) SCE, 0.1M Bu4NClO4 Product

4'-Allyl-1,3-benzodioxol

Description (Energy Data (MCS))

Enthalpy of mixtures

Partner (Energy Data (MCS))

ozone

Briner; Ryffel; de Nemitz; Helvetica Chimica Acta; vol. 21; (1938); p. 357,362, View in Reaxys Further Information (3) Description (Fur- References ther Information) Further information

Voronkov; Lapina; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 2; (1966); p. 390,391; Khimiya Geterotsiklicheskikh Soedinenii; vol. 2; (1966); p. 522, View in Reaxys

Further information

Takegami et al.; Bulletin of the Chemical Society of Japan; vol. 38; (1965); p. 1279,1281, 1282, View in Reaxys

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Further information

?orjaschtschew, Woronin; J. Anal. Chem. USSR (Engl. Transl.); vol. 18; (1963); p. 401,351, View in Reaxys

Liquid/Vapour Systems (MCS) (1) 1 of 1

Description (Liquid/ Boiling points of mixtures Vapour Systems (MCS)) Pressure (Liquid/Vapour 10 Systems (MCS)) [Torr] Partner (Liquid/Vapour Systems (MCS))

phenol

Brauer; Ber. Schimmel; (1929); p. 151,160, View in Reaxys Mechanical Properties (1) Description (MeReferences chanical Properties) Viscosity

Koul; Nigam; Riechstoffe und Aromen; vol. 17; (1967); p. 269,270, View in Reaxys

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Optical Rotatory Power [deg]

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Nigam; Ramaiah; Riechstoffe und Aromen; vol. 22; (1972); p. 378,388, View in Reaxys Optics (2) Description (Optics) Electric birefringence (Kerr effect)

Comment (Optics)

References

Kerr-Konstante.

Pauthenier; Bart; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 192; (1931); p. 352, View in Reaxys

Magnetic birefringence (CottonMouton effect)

Cotton; Mouton; Annales de Chimie (Cachan, France); vol. <8> 28; (1913); p. 215, View in Reaxys

Other Thermochemical Data (2) Description (Oth- Comment (Other er Thermochemi- Thermochemical cal Data) Data)

References

Cryoscopic constant

fuer 1 kg Loesungsmittel: 5.7.

Sanderson; Jones; Journal of the Society of Chemical Industry, London; vol. 42; (1923); p. 1 T, View in Reaxys

Heat of combustion at constant volume

1243.8 kcal/Mol.

Stohmann; Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre; vol. 10; (1892); p. 415, View in Reaxys

Partition octan-1-ol/water (MCS) (1) 1 of 1

log POW

3.18

Smith; Perfetti; Garg; Hansch; Food and Chemical Toxicology; vol. 41; nb. 6; (2003); p. 807 - 817, View in Reaxys Surface Tension (1) References Koul; Nigam; Riechstoffe und Aromen; vol. 17; (1967); p. 269,270, View in Reaxys Transport Phenomena (MCS) (2) 1 of 2

Description (Transport Phenomena (MCS))

Viscosity

Koul; Nigam; Riechstoffe und Aromen; vol. 17; (1967); p. 269,270, View in Reaxys

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2 of 2

Description (Transport Phenomena (MCS))

Viscosity

Partner (Transport Phenomena (MCS))

3-methyl-1-butyl acetate

Dunstan; Hilditch; Zeitschrift fuer Elektrochemie und Angewandte Physikalische Chemie; vol. 18; (1912); p. 187,884, View in Reaxys NMR Spectroscopy (19) 1 of 19

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- [(2)H6]acetone scopy) Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Bergami, Matteo; Protti, Stefano; Ravelli, Davide; Fagnoni, Maurizio; Advanced Synthesis and Catalysis; vol. 358; nb. 7; (2016); p. 1164 - 1172, View in Reaxys 2 of 19

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- [(2)H6]acetone scopy) Frequency (NMR Spectroscopy) [MHz]

Location

supporting information

Bergami, Matteo; Protti, Stefano; Ravelli, Davide; Fagnoni, Maurizio; Advanced Synthesis and Catalysis; vol. 358; nb. 7; (2016); p. 1164 - 1172, View in Reaxys 3 of 19

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Ou, Wenhua; Huang, Hong; Asian Journal of Chemistry; vol. 27; nb. 3; (2015); p. 1175 - 1176, View in Reaxys 4 of 19

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Reichl, Kyle D.; Dunn, Nicole L.; Fastuca, Nicholas J.; Radosevich, Alexander T.; Journal of the American Chemical Society; vol. 137; nb. 16; (2015); p. 5292 - 5295, View in Reaxys 5 of 19

Description (NMR Spec- Chemical shifts troscopy)

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Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- [(2)H6]acetone scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

600

Location

supporting information

Larsen, Casey R.; Paulson, Erik R.; Erdogan, Gulin; Grotjahn, Douglas B.; Synlett; vol. 26; nb. 17; (2015); p. 2462 - 2466; Art.No: ST-2015-B0231-L, View in Reaxys 6 of 19

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Levin, Mark D.; Toste, F. Dean; Angewandte Chemie - International Edition; vol. 53; nb. 24; (2014); p. 6211 - 6215; Angew. Chem.; vol. 126; nb. 24; (2014); p. 6325 - 6329,5, View in Reaxys 7 of 19

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Du, Shu-Shan; Yang, Kai; Wang, Cheng-Fang; You, Chun-Xue; Geng, Zhu-Feng; Guo, Shan-Shan; Deng, ZhiWei; Liu, Zhi-Long; Chemistry and Biodiversity; vol. 11; nb. 9; (2014); p. 1449 - 1456, View in Reaxys 8 of 19

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Location

supporting information

Bhattacherjee, Abhishek; Datta, Abhijit; Ghosh, Tanushree; Sil, Rajarshi; Natural Product Research; vol. 28; nb. 23; (2014); p. 2199 - 2202, View in Reaxys

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10 of 19

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Original Text (NMR Spectroscopy)

13C-NMR

Comment (NMR Spectroscopy)

Signals given

(125 MHz, CDCl3): δ 133.4 (C-I), 108.0 (C-2), 147.3 (C-3), 145.5 (C-4), 108.8 (C-5), 121.1 (C-6), 40.0 (C-7), 137.8 (C-8), 115.4 (C-9), 100.7 (-OCH2O-)

Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; WO2008/96998; (2008); (A1) English, View in Reaxys 11 of 19

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

1H-NMR (300 MHz, CDCl ): δ 3.22 (2H, d, J = 6.6 Hz, H-7), δ 5.00 (IH, m, H-9a), δ 5.02 3 (IH, m, H-9b), δ 5.85 (IH, m, H-8), δ 5.83 (2H, s, - OCH2O-), δ 6.58 (IH, J = 8.1 Hz, H-6), δ 6.63 (IH, m, H-2), δ 6.67 (IH, d, J = 8.1 Hz, H-5);

Comment (NMR Spectroscopy)

Signals given

Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; WO2008/96998; (2008); (A1) English, View in Reaxys 12 of 19

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Protti, Stefano; Fagnoni, Maurizio; Albini, Angelo; Organic and Biomolecular Chemistry; vol. 3; nb. 15; (2005); p. 2868 - 2871, View in Reaxys 13 of 19

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Datta, Swarup; Chang, Chia-Lung; Yeh, Kuo-Liang; Liu, Rai-Shung; Journal of the American Chemical Society; vol. 125; nb. 31; (2003); p. 9294 - 9295, View in Reaxys 14 of 19

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

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Datta, Swarup; Chang, Chia-Lung; Yeh, Kuo-Liang; Liu, Rai-Shung; Journal of the American Chemical Society; vol. 125; nb. 31; (2003); p. 9294 - 9295, View in Reaxys 15 of 19

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Datta, Swarup; Chang, Chia-Lung; Yeh, Kuo-Liang; Liu, Rai-Shung; Journal of the American Chemical Society; vol. 125; nb. 31; (2003); p. 9294 - 9295, View in Reaxys 16 of 19

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Sy, Lai-King; Saunders, Richard M. K.; Brown, Geoffrey D.; Phytochemistry; vol. 44; nb. 6; (1997); p. 1099 1108, View in Reaxys 17 of 19

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Sy, Lai-King; Saunders, Richard M. K.; Brown, Geoffrey D.; Phytochemistry; vol. 44; nb. 6; (1997); p. 1099 1108, View in Reaxys 18 of 19

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Yakushijin, Kenichi; Tohshima, Tomoko; Suzuki, Rika; Murata, Hiroyuki; Lu, Sheng-Ten; Furukawa, Hiroshi; Chemical & Pharmaceutical Bulletin; vol. 31; nb. 8; (1983); p. 2879 - 2883, View in Reaxys 19 of 19

Description (NMR Spec- NMR troscopy) Femino et al.; Steroids; vol. 23; (1974); p. 869,876, View in Reaxys

IR Spectroscopy (8) 1 of 8

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Ou, Wenhua; Huang, Hong; Asian Journal of Chemistry; vol. 27; nb. 3; (2015); p. 1175 - 1176, View in Reaxys 2 of 8

Description (IR Spectroscopy)

ATR (attenuated total reflectance); Bands; Spectrum

Wang, Lai-Hao; Chang, Chia-Ling; Hu, Yi-Chun; Croatica Chemica Acta; vol. 88; nb. 1; (2015); p. 35 - 42, View in Reaxys 3 of 8

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Datta, Swarup; Chang, Chia-Lung; Yeh, Kuo-Liang; Liu, Rai-Shung; Journal of the American Chemical Society; vol. 125; nb. 31; (2003); p. 9294 - 9295, View in Reaxys

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4 of 8

Description (IR Spectroscopy)

Noguchi; Kitajima; Nippon Rin Gakkaishi; vol. 41; (1959); p. 488,489-494; Chem.Abstr.; nb. 25075; (1960), View in Reaxys; Fujita; Yamashita; Bulletin of the Chemical Society of Japan; vol. 46; (1973); p. 3553, View in Reaxys; Fujita; Fujita; Chemical and Pharmaceutical Bulletin; vol. 20; (1972); p. 2251, View in Reaxys; Messerschmidt; Arzneimittel-Forschung; vol. 18; nb. 12; (1968); p. 1618 - 1618, View in Reaxys 5 of 8

Description (IR Spectroscopy)

Spectrum

Comment (IR Spectroscopy)

1700 - 700 cm**(-1)

Naves; Ardizio; Bulletin de la Societe Chimique de France; (1957); p. 1053,1056, View in Reaxys 6 of 8

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

1640 - 770 cm**(-1)

Naves; Ardizio; Bulletin de la Societe Chimique de France; (1957); p. 1053,1056, View in Reaxys 7 of 8

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CCl4

Comment (IR Spectroscopy)

2910 - 2780 cm**(-1)

Briggs et al.; Analytical Chemistry; vol. 29; (1957); p. 904,905, View in Reaxys 8 of 8

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

1440 - 710 cm**(-1)

Briggs et al.; Analytical Chemistry; vol. 29; (1957); p. 904,905, View in Reaxys Mass Spectrometry (9) Description (Mass Location Spectrometry)

Comment (Mass Spectrometry)

electrospray ionisation (ESI); spectrum high resolution mass spectrometry (HRMS); electron impact (EI); spectrum

References Ou, Wenhua; Huang, Hong; Asian Journal of Chemistry; vol. 27; nb. 3; (2015); p. 1175 - 1176, View in Reaxys

supporting information

Reichl, Kyle D.; Dunn, Nicole L.; Fastuca, Nicholas J.; Radosevich, Alexander T.; Journal of the American Chemical Society; vol. 137; nb. 16; (2015); p. 5292 - 5295, View in Reaxys

gas chromatography mass spectrometry (GCMS); electron impact (EI); spectrum

MALDI (Matrix as- supporting inforsisted laser demation sorption ionization); time-of-flight mass spectra (TOFMS); spectrum

Bhattacherjee, Abhishek; Datta, Abhijit; Ghosh, Tanushree; Sil, Rajarshi; Natural Product Research; vol. 28; nb. 23; (2014); p. 2199 - 2202, View in Reaxys

electron impact (EI); spectrum

Pinalli, Roberta; Barboza, Tahnee; Bianchi, Federica; Massera, Chiara; Ugozzoli, Franco; Dalcanale, Enrico; Supramolecular Chemistry; vol. 25; nb. 9-11; (2013); p. 682 - 687, View in Reaxys

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GCMS (Gas chromatography mass spectrometry); Spectrum

Razavi, Seyed Mehdi; Nazemiyeh, Hossein; Delazar, Abbas; Asnaashari, Solmaz; Hajiboland, Rogaieh; Sarker, Satyajit D.; Omidi, Yadollah; Natural Product Research; vol. 25; nb. 7; (2011); p. 663 - 668, View in Reaxys

EI (Electron impact)

Molecular peak

Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; WO2008/96998; (2008); (A1) English, View in Reaxys

GCMS (Gas chromatography mass spectrometry)

Molecular peak

Patent; Mitra, Shankar Kumar; Saxena, Ekta; Ranganna, Marikunte Venkata; US2005/266101; (2005); (A1) English, View in Reaxys

spectrum; chemical ionization (CI)

Lange, G.; Schultze, W.; Organic Mass Spectrometry; vol. 27; nb. 4; (1992); p. 481 - 488, View in Reaxys

UV/VIS Spectroscopy (9) 1 of 9

Description (UV/VIS Spectroscopy)

UV/VIS

Messerschmidt; Arzneimittel-Forschung; vol. 18; nb. 12; (1968); p. 1618 - 1618, View in Reaxys 2 of 9

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

ethanol

Absorption Maxima (UV/ 236; 285 VIS) [nm] Naves; Ardizio; Bulletin de la Societe Chimique de France; (1957); p. 1053,1056, View in Reaxys 3 of 9

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

2,2,4-trimethyl-pentane

Absorption Maxima (UV/ 236.5; 285; 289 VIS) [nm] Naves; Ardizio; Bulletin de la Societe Chimique de France; (1957); p. 1053,1056, View in Reaxys 4 of 9

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

ethanol

Absorption Maxima (UV/ 237; 286 VIS) [nm] Patterson; Hibbert; Journal of the American Chemical Society; vol. 65; (1943); p. 1862,1864, View in Reaxys 5 of 9

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

hexane

Comment (UV/VIS Spectroscopy)

220 - 310 nm

Herzog; Hillmer; Chemische Berichte; vol. 64; (1931); p. 1288,1305, View in Reaxys; Hillmer; Schorning; Zeitschrift fuer Physikalische Chemie, Abteilung A: Chemische Thermodynamik, Kinetik, Elektrochemie, Eigenschaftslehre; vol. 167; (1934); p. 407,415, View in Reaxys 6 of 9

Description (UV/VIS Spectroscopy)

Spectrum

Comment (UV/VIS Spectroscopy)

240 - 320 nm

Ramart-Lucas; Amagat; Bulletin de la Societe Chimique de France; vol. <4> 51; (1932); p. 108,117, View in Reaxys 7 of 9

Description (UV/VIS Spectroscopy)

Spectrum

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Ramart-Lucas; Amagat; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 188; (1929); p. 639, View in Reaxys 8 of 9

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

ethanol

Crymble; Stewart; Wright; Glendinning; So.; vol. 99; p. 455, View in Reaxys 9 of 9

Description (UV/VIS Spectroscopy)

Spectrum

Comment (UV/VIS Spectroscopy)

1000 - 15000 nm; im Ultrarot.

Coblentz,W. W.; Investigations of infra-red-spectra <Washington 1905>, S. 81, 140, 164, 241, View in Reaxys Raman Spectroscopy (2) Description (Ram- References an Spectroscopy) Spectrum; Bands

Wang, Lai-Hao; Chang, Chia-Ling; Hu, Yi-Chun; Croatica Chemica Acta; vol. 88; nb. 1; (2015); p. 35 - 42, View in Reaxys

Bands

Chabeau; Bl. Acad. Med. Belgique; vol. <6> 3; (1938); p. 46,64, View in Reaxys; Morris; Phys. Rad.; vol. <2> 38; (1931); p. 141,143, View in Reaxys; Dupont; Dulou; Bulletin de la Societe Chimique de France; vol. <5> 3; (1936); p. 1639,1659, View in Reaxys; Susz; Perrottet; Briner; Helvetica Chimica Acta; vol. 19; (1936); p. 548,554,556, View in Reaxys

Fluorescence Spectroscopy (1) Description (Fluo- Solvent (Fluoresrescence Speccence Spectrotroscopy) scopy)

Comment (Fluorescence Spectroscopy)

References

Maxima

330 nm

Schreiber-Deturmeny; Pauli; Pastor; Journal of Pharmaceutical Sciences; vol. 82; nb. 8; (1993); p. 813 - 816, View in Reaxys

acetonitrile; various solvent(s)

Pharmacological Data (102) 1 of 102

Comment (Pharmacological Data)

Bioactivities present

Riemschneider,R.; Grabitz,B.E.; Monatshefte fuer Chemie; vol. 91; (1960); p. 22 - 40, View in Reaxys; Gilbert,E.E.; Canadian Journal of Chemistry; vol. 48; (1970); p. 730 - 734, View in Reaxys; Patent; Rhone-Poulenc S. A.; US4138411; (1979); (A1) English, View in Reaxys; Patent; Bayer Aktiengesellschaft; US4212809; (1980); (A1) English, View in Reaxys; Huisgen,R. et al.; Chemische Berichte; vol. 100; nb. 5; (1967); p. 1580 - 1592, View in Reaxys; Gotthardt,H.; Huisgen,R.; Chemische Berichte; vol. 101; (1968); p. 552 - 563, View in Reaxys; Huisgen,R. et al.; Chemische Berichte; vol. 101; nb. 6; (1968); p. 2043 - 2055, View in Reaxys; Patent; Montedison S.p.A.; US4731482; (1988); (A1) English, View in Reaxys; Schulte; von Weissenborn; Archiv der Pharmazie; vol. 305; nb. 5; (1972); p. 354 - 359, View in Reaxys; Barton,D.H.R.; Jones,D.W.; Journal of the Chemical Society; (1965); p. 3563 - 3570, View in Reaxys; Patent; Eisai Co., Ltd.; US5110956; (1992); (A1) English, View in Reaxys; Hassner; Arnold; Gault; Terada; Tetrahedron letters; vol. 10; (1968); p. 1241 - 1245, View in Reaxys; Colonna,M.; Bruni,P.; Gazzetta Chimica Italiana; vol. 95; (1965); p. 245 - 256, View in Reaxys; Cabiddu,S. et al.; Gazzetta Chimica Italiana; vol. 98; (1968); p. 800 - 809, View in Reaxys; Tressl,R. et al.; Z. Naturforsch., B: Anorg. Chem., Org. Chem., Biochem., Biophys.,; vol. 24; (1969); p. 781 - 783, View in Reaxys; Patent; Bartholomaus, Johannes; Kugelmann, Heinrich; US2005/31546; (2005); (A1) English, View in Reaxys; Patent; Henrich, Vincent C.; Weinberger, Cary Alan; US2005/49230; (2005); (A1) English, View in Reaxys; Patent; Mitra, Shankar Kumar; Saxena, Ekta; Ranganna, Marikunte Venkata; US2005/266101; (2005); (A1) English, View in Reaxys; Patent; University of Maryland; US7091238; (2006); (B1) English, View in Reaxys; Patent; LIFECYCLE PHARMA A/S; WO2006/136175; (2006); (A2) English, View in Reaxys; Foulds; Robinson; Journal of the Chemical Society; vol. 105; (1914); p. 1966, View in Reaxys; Henrard; Chem. Zentralbl.; vol. 78; nb. II; (1907); p. 1512, View in Reaxys; Patent; Merck; DE274350; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 12; p. 768, View in Reaxys; Woy; Archiv der Pharmazie (Weinheim, Germany); vol. 228; (1890); p. 40, View in Reaxys; Ciamician; Silber; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5> 18 I; (1909); p. 218; Chemische Berichte; vol. 42; (1909); p. 1389, View in Reaxys; Eijkman; Chemische Berichte; vol. 23; (1890); p. 862, View in Reaxys; Knoll,R.; Synthetische und isolierte Riechstoffe und deren Darstellung <Halle 1908>, S. 85, View in Reaxys; Wagner; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 29; (1897); p. 17 Anm. 5; Chem. Zentralbl.; vol. 68; nb. I; (1897); p. 914, View in Reaxys; Angeli; Gazzetta Chimica Italiana; vol. 23 II; (1893); p. 101, View in Reaxys; Poleck; Chemische Berichte; vol. 17; (1884); p. 1940, View in Reaxys; Schiff; Chemische Berichte; vol. 17; (1884); p. 1937, View in Reaxys; Balbiano; Paolini; Luzzi; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5> 11 II; (1902); p. 69; Chemische Berichte; vol. 35; (1902); p. 2997, View in Reaxys; Balbiano; Paolini; Luzzi; Chemische Berichte; vol. 36; (1903); p. 3579; Gazzetta Chimica Italiana; vol. 36 I; (1906); p. 270, View in Reaxys; Manchot; Justus Liebigs Annalen der Chemie; vol. 421; (1920); p. 320, View in Reaxys; Tsukamoto; Journ. Pharm. Soc. of Japan; (1930); p.

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3, View in Reaxys; Patent; Pomeranz; DE122701, View in Reaxys; Grimaux; Ruotte; Bulletin de la Societe Chimique de France; vol. <2> 11; (1869); p. 465; Justus Liebigs Annalen der Chemie; vol. 152; (1869); p. 91, View in Reaxys; Power; Lees; Journal of the Chemical Society; vol. 85; (1904); p. 638, View in Reaxys; Miller; Archiv der Pharmazie (Weinheim, Germany); vol. 240; (1902); p. 377, View in Reaxys; Wagner; Bouschmakin; Chemische Berichte; vol. 24; (1891); p. 3489, View in Reaxys; Tiemann; Chemische Berichte; vol. 24; (1891); p. 2881, View in Reaxys; Poleck; Chemische Berichte; vol. 19; (1886); p. 1094; Chemische Berichte; vol. 22; (1889); p. 2862, View in Reaxys; Eijkman; Recueil des Travaux Chimiques des Pays-Bas; vol. 4; (1885); p. 39, View in Reaxys; Patent; Otto; Verley; DE97620; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 4; p. 1281, View in Reaxys; Harries; Adam; Chemische Berichte; vol. 49; (1916); p. 1029, View in Reaxys; Stohmann; Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre; vol. 10; (1892); p. 415, View in Reaxys; Schimmel and Co.; Chem. Zentralbl.; vol. 73; nb. I; (1902); p. 1060, View in Reaxys; v. Rechenberg,C.; Einfache und fraktionierte Destillation, 2. Aufl. <Miltitz 1923>, S. 261, View in Reaxys; Flueckiger; Annalen der Physik (Weinheim, Germany); vol. 158; (1876); p. 248, View in Reaxys; Knoll,R.; Synthetische und isolierte Riechstoffe <Halle 1908>, S. 63, View in Reaxys; Semmler; Die aetherischen Oele, Bd. IV <Leipzig 1907>, S. 144ff, View in Reaxys; Goulding; Journal of the Chemical Society; vol. 83; (1903); p. 1099, View in Reaxys; Schimmel and Co.; Bericht vom September 1885, 7, View in Reaxys; Pilgrim; Chem. Zentralbl.; vol. 80; nb. I; (1909); p. 534, View in Reaxys; Power; Kleber; Chem. Zentralbl.; vol. 68; nb. II; (1897); p. 42, View in Reaxys; Saint-Evre; Annales de Chimie (Cachan, France); vol. <3> 12; (1844); p. 107; Justus Liebigs Annalen der Chemie; vol. 52; (1844); p. 397, View in Reaxys; Binder; Buchners Repertorium fuer die Pharmacie 11 <1821>, 346, View in Reaxys; Semmler; Bartelt; Chemische Berichte; vol. 41; (1908); p. 2752, View in Reaxys; Tiffeneau; Daufresne; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 144; (1907); p. 926; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 145; (1907); p. 629, View in Reaxys; Ciamician; Silber; Gazzetta Chimica Italiana; vol. 20; (1890); p. 571; Chemische Berichte; vol. 23; (1890); p. 1160, View in Reaxys; Angeli; Rimini; Gazzetta Chimica Italiana; vol. 25 II; (1895); p. 205, View in Reaxys; Anderlini; Gazzetta Chimica Italiana; vol. 23 I; (1893); p. 130, View in Reaxys; Paolini; Luzzi; Balbiano; Gazzetta Chimica Italiana; vol. 36 I; (1906); p. 273; Chemische Berichte; vol. 36; (1903); p. 3579, View in Reaxys; Balbiano; Paolini; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5> 11 II; (1902); p. 69; Chemische Berichte; vol. 35; (1902); p. 2998, View in Reaxys; Paolini; Luzzi; Balbiano; Gazzetta Chimica Italiana; vol. 36 I; (1906); p. 272; Chemische Berichte; vol. 36; (1903); p. 3579, View in Reaxys; Fourneau; Tiffeneau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 141; (1905); p. 662; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 140; (1905); p. 1595, View in Reaxys; Prins; Chem. Zentralbl.; vol. 90; nb. III; (1919); p. 1001, View in Reaxys; Angeli; Alessandri; Pegna; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5> 19 I; (1910); p. 654, View in Reaxys; Abati; Gazzetta Chimica Italiana; vol. 40 II; (1910); p. 92, View in Reaxys; Luff; Perkin; Robinson; Journal of the Chemical Society; vol. 97; (1910); p. 1139, View in Reaxys; Crymble; Stewart; Wright; Glendinning; So.; vol. 99; p. 455, View in Reaxys; Schimmel and Co.; Chem. Zentralbl.; vol. 82; nb. I; (1911); p. 1837, View in Reaxys; Hargreaves; Journal of the Chemical Society; vol. 109; (1916); p. 751, View in Reaxys; Pickles; Journal of the Chemical Society; vol. 101; (1912); p. 1437, View in Reaxys; Scott; Journal of the Chemical Society; vol. 101; (1912); p. 1613, View in Reaxys; Schimmel and Co.; Chem. Zentralbl.; vol. 81; nb. I; (1910); p. 1719, View in Reaxys; Decker; Justus Liebigs Annalen der Chemie; vol. 395; (1913); p. 295, View in Reaxys; Brochet; Bauer; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 159; (1914); p. 191; Bulletin de la Societe Chimique de France; vol. <4> 17; (1915); p. 52, View in Reaxys; Kafuku; Acta Phytochimica; vol. 2; (1924); p. 117; Yakugaku Zasshi; nb. 521; (1925); p. 1; Chem. Zentralbl.; vol. 97; nb. I; (1926); p. 69, View in Reaxys; Spaeth; Quietensky; Chemische Berichte; vol. 60; (1927); p. 1887, View in Reaxys; Rosenmund; Kuhnhenn; Chemische Berichte; vol. 56; (1923); p. 1265, View in Reaxys; Kern; Shriner; Adams; Journal of the American Chemical Society; vol. 47; (1925); p. 1149, View in Reaxys; Lecat,M.; Recueil des Travaux Chimiques des Pays-Bas; vol. 47; (1928); p. 15,16; Ann. Soc. scient. Bruxelles; vol. 47 I; (1927); p. 154, View in Reaxys; Wagner; Riechstoffind.; (1926); p. 52; Chem. Zentralbl.; vol. 97; nb. II; (1926); p. 1209, View in Reaxys; Ramart-Lucas; Amagat; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 188; (1929); p. 638, View in Reaxys; Robinson; Zaki; Journal of the Chemical Society; (1927); p. 2489, View in Reaxys; Horiuchi; Nippon Kagaku Kaishi; vol. 47; p. 357; Chem. Zentralbl.; vol. 98; nb. II; (1927); p. 368, View in Reaxys; Hirao; J. Soc. chem. Ind. Japan Spl.; vol. 30; p. 24 B; Chem. Zentralbl.; vol. 100; nb. II; (1929); p. 2045, View in Reaxys; Kafuku; Yakugaku Zasshi; nb. 521; (1925); p. 1; Chem. Zentralbl.; vol. 97; nb. I; (1926); p. 69, View in Reaxys; Alessandri; Gazzetta Chimica Italiana; vol. 54; (1924); p. 449, View in Reaxys; Boeeseken; Elsen; Recueil des Travaux Chimiques des Pays-Bas; vol. 48; (1929); p. 367, View in Reaxys; Wagner; Chemiker-Zeitung, Chemische Apparatur; vol. 52; (1928); p. 379; Chem. Zentralbl.; vol. 99; nb. I; (1928); p. 3056, View in Reaxys; Patent; Riedel-de Haen; DE505404; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 17; p. 569,571, View in Reaxys; Patent; Riedel-de Haen; DE507796, View in Reaxys; Patent; Riedel,J. D.; Boedecker; GB285156, View in Reaxys; Patent; Riedel,J. D.; Boedecker; GB285551, View in Reaxys; Schmidt; Bartholome; Chemische Berichte; vol. 57; (1924); p. 2040, View in Reaxys; Waterman; Priester; Recueil des Travaux Chimiques des Pays-Bas; vol. 47; (1928); p. 1033, View in Reaxys; Lebedew; Platonow; Journal of the Chemical Society; (1930); p. 332,333; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 61; (1929); p. 2165,2166, View in Reaxys; Lebedew; Jakubtschik; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 60; (1928); p. 816,827; Chem. Zentralbl.; vol. 99; nb. II; (1928); p. 1315, View in Reaxys; Armstrong; Hilditch; Proceedings of the Royal Society of London, Series A: Mathematical, Physical and Engineering Sciences; vol. 98; (1921); p. 29; Chem. Zentralbl.; vol. 92; nb. I; (1921); p. 650, View in Reaxys; Sanderson; Jones; Journal of the Society of Chemical Industry, London; vol. 42; (1923); p. 1 T, View in Reaxys; Coblentz,W. W.; Investigations of infra-red-spectra <Washington 1905>, S. 81, 140, 164, 241, View in Reaxys; Ramart-Lucas; Amagat; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 188; (1929); p. 639, View in Reaxys; Perkin; Trikojus; Journal of the Chemical Society; (1927); p. 1665, View in Reaxys; Anonymus; Chem. Zentralbl.; vol. 91; nb. III; (1920); p. 597, View in Reaxys; Fester; Salgado;

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Angewandte Chemie; vol. 42; (1929); p. 988, View in Reaxys; Schimmel and Co.; Ber. Schimmel 1927, 61; C. 1927 II, 1518, View in Reaxys; Roure-Bertrand fils; Chem. Zentralbl.; vol. 93; nb. I; (1922); p. 360, View in Reaxys; Penfold; Perfumery and Essential Oil Record; vol. 13; p. 273; Chem. Zentralbl.; vol. 93; nb. IV; (1922); p. 673, View in Reaxys; Patent; Merck,E.; DE478844; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 2907, View in Reaxys; Mosettig; Chemische Berichte; vol. 62; (1929); p. 1274, View in Reaxys; Nagai; J. Fac. Eng. Tokyo Univ.; vol. 13; p. 185; Chem. Zentralbl.; vol. 94; nb. 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Comment (Pharmacological Data)

physiological behaviour discussed

Madrid, Alejandro; Godoy, Patricio; Gonzlez, Sebastin; Zaror, Luis; Moller, Alejandra; Werner, Enrique; Cuellar, Mauricio; Villena, Joan; Montenegro, Ivn; Molecules; vol. 20; nb. 5; (2015); p. 8033 - 8047, View in Reaxys 3 of 102

Comment (Pharmacological Data)

physiological behaviour discussed

Effect (Pharmacological Data)

antifeedant

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Species or Test-System (Pharmacological Data)

Drosophila melanogaster til-til

Concentration (Pharmacological Data)

5 ppm

Further Details (Pharmacological Data)

antifeedant index (AI)

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

33.21 percent

Montenegro, Ivan; Pino, Luis; Werner, Enrique; Madrid, Alejandro; Espinoza, Luis; Moreno, Luis; Villena, Joan; Cuellar, Mauricio; Molecules; vol. 18; nb. 4; (2013); p. 4192 - 4208, View in Reaxys 5 of 102

Effect (Pharmacological Data)

body weight; effect on

Species or Test-System (Pharmacological Data)

Drosophila melanogaster til-til

Concentration (Pharmacological Data)

5 mg/l

Type (Pharmacological Data)

percent weight to control

Value of Type (Pharmacological Data)

33.2 percent

Effect (Pharmacological Data)

larvicidal

Species or Test-System (Pharmacological Data)

Drosophila melanogaster til-til

Further Details (Pharmacological Data)

20percent mortality at 168 h; effective concentration (EC)

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

18 mg/ml

Comment (Pharmacological Data)

physiological behaviour discussed

Sharma, Upendra K.; Sood, Swati; Sharma, Nandini; Rahi, Praveen; Kumar, Rakesh; Sinha, Arun K.; Gulati, Arvind; Medicinal Chemistry Research; vol. 22; nb. 11; (2013); p. 5129 - 5140, View in Reaxys 8 of 102

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or Test-System (Pharmacological Data)

CYP1A2

Kind of Dosing (Pharmacological Data)

comparative comp. dissolved in methanol

Further Details (Pharmacological Data)

CYP: cytochrome P450

Results

molecular target: CYP1A2

Brahmi, Zeineb; Katho, Tatsuya; Hatsumata, Rie; Hiroi, Asako; Miyakawa, Nami; Yakou, Emi; Sugaya, Kouichi; Onose, Jun-Ichi; Abe, Naoki; Bioscience, Biotechnology and Biochemistry; vol. 76; nb. 5; (2012); p. 1028 1031, View in Reaxys

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9 of 102

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or Test-System (Pharmacological Data)

CYP1A2

Kind of Dosing (Pharmacological Data)

comparative comp. dissolved in methanol

Further Details (Pharmacological Data)

CYP: cytochrome P450; inhibitory concentration (IC)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

3.9 μmol/l

Effect (Pharmacological Data)

antiproliferative

Species or Test-System (Pharmacological Data)

MCF-7 cells

Kind of Dosing (Pharmacological Data)

title comp. dissolved in EtOH

Further Details (Pharmacological Data)

sulforhodamine B assay; IC50: concentration that produces 50percent cell growth inhibition; MCF-7: human breast cancer cell line; inhibitory concentration (IC)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 100 μmol/l

Villegas, Alejandro Madrid; Catalan, Luis Espinoza; Venegas, Ivan Montenegro; Garcia, Joan Villena; Altamirano, Hector Carrasco; Molecules; vol. 16; nb. 6; (2011); p. 4632 - 4641, View in Reaxys 11 of 102

Effect (Pharmacological Data)

antiproliferative

Species or Test-System (Pharmacological Data)

MDA-MB-231 cells

Kind of Dosing (Pharmacological Data)

title comp. dissolved in EtOH

Further Details (Pharmacological Data)

sulforhodamine B assay; IC50: concentration that produces 50percent cell growth inhibition; MDA-MB-231: human breast cancer cell line; inhibitory concentration (IC)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 100 μmol/l

Effect (Pharmacological Data)

antiproliferative

Species or Test-System (Pharmacological Data)

DHF cells

Kind of Dosing (Pharmacological Data)

title comp. dissolved in EtOH

Further Details (Pharmacological Data)

sulforhodamine B assay; IC50: concentration that produces 50percent cell growth inhibition; DHF: dermal human fibroblast; inhibitory concentration (IC)

Type (Pharmacological Data)

IC50

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Value of Type (Pharmacological Data)

> 100 μmol/l

Effect (Pharmacological Data)

transporter; stimulation of

Species or Test-System (Pharmacological Data)

HEK293-Flp-In cells; genetically modified/infected with: human OCT2

Concentration (Pharmacological Data)

20 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Further Details (Pharmacological Data)

OCT2: organic cation transporter 2 (solute carrier 22A2); HEK: human embryonic kidney; fluorescent probe substrate: 4-(4-(dimethylamino)styryl)-N-methyl-pyridinium (ASP+) (5 μmol/l); high-throughput assay; fluorimetry; stimulation rate related to: OCT2

Type (Pharmacological Data)

stimulation rate

Value of Type (Pharmacological Data)

7.9 percent

Location

supporting information

Kido, Yasuto; Matsson, Paer; Giacomini, Kathleen M.; Journal of Medicinal Chemistry; vol. 54; nb. 13; (2011); p. 4548 - 4558, View in Reaxys 14 of 102

Effect (Pharmacological Data)

transporter; stimulation of

Species or Test-System (Pharmacological Data)

HEK293-Flp-In cells; genetically modified/infected with: human OCT2

Concentration (Pharmacological Data)

20 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Further Details (Pharmacological Data)

Results

molecular target: human OCT2

Location

supporting information

Kido, Yasuto; Matsson, Paer; Giacomini, Kathleen M.; Journal of Medicinal Chemistry; vol. 54; nb. 13; (2011); p. 4548 - 4558, View in Reaxys 15 of 102

Effect (Pharmacological Data)

miticidal

Species or Test-System (Pharmacological Data)

Dermatophagoides farinae

Kind of Dosing (Pharmacological Data)

title comp. dissolved in acetone

Further Details (Pharmacological Data)

impregnated fabric disk assay; lethal concentration (LC)

Type (Pharmacological Data)

LC50

Value of Type (Pharmacological Data)

10.5 μg/cm2

Song, Ha Yun; Yang, Ji Yeon; Suh, Joo Won; Lee, Hoi Seon; Journal of Agricultural and Food Chemistry; vol. 59; nb. 14; (2011); p. 7759 - 7764, View in Reaxys 16 of 102

Effect (Pharmacological Data)

miticidal

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Species or Test-System (Pharmacological Data)

Dermatophagoides pteronyssinus

Kind of Dosing (Pharmacological Data)

title comp. dissolved in acetone

Further Details (Pharmacological Data)

impregnated fabric disk assay; lethal concentration (LC)

Type (Pharmacological Data)

LC50

Value of Type (Pharmacological Data)

14.5 μg/cm2

Song, Ha Yun; Yang, Ji Yeon; Suh, Joo Won; Lee, Hoi Seon; Journal of Agricultural and Food Chemistry; vol. 59; nb. 14; (2011); p. 7759 - 7764, View in Reaxys 17 of 102

Effect (Pharmacological Data)

miticidal

Species or Test-System (Pharmacological Data)

Tyrophagus putrescentiae

Kind of Dosing (Pharmacological Data)

title comp. dissolved in acetone

Further Details (Pharmacological Data)

impregnated fabric disk assay; lethal concentration (LC)

Type (Pharmacological Data)

LC50

Value of Type (Pharmacological Data)

4.25 μg/cm2

Song, Ha Yun; Yang, Ji Yeon; Suh, Joo Won; Lee, Hoi Seon; Journal of Agricultural and Food Chemistry; vol. 59; nb. 14; (2011); p. 7759 - 7764, View in Reaxys 18 of 102

Effect (Pharmacological Data)

larvicidal

Species or Test-System (Pharmacological Data)

second instar larvae of Spodoptera litura

Kind of Dosing (Pharmacological Data)

title comp. dissolved in acetone and then diluted with water; larvae transferred on Ricinus communis leaf disks dipped in title comp. solution with concentration 15 μg/cm2

Further Details (Pharmacological Data)

PDP is time-dependent

Type (Pharmacological Data)

percent mortality

Value of Type (Pharmacological Data)

96 - 100 percent

Bhardwaj, Anu; Tewary, Dhananjay Kumar; Kumar, Rakesh; Kumar, Vinod; Sinha, Arun Kumar; Shanker, Adarsh; Chemistry and Biodiversity; vol. 7; nb. 1; (2010); p. 168 - 177, View in Reaxys 19 of 102

Effect (Pharmacological Data)

larvicidal

Species or Test-System (Pharmacological Data)

second instar larvae of Spodoptera litura

Kind of Dosing (Pharmacological Data)

title comp. dissolved in acetone and then diluted with water; larvae transferred on Ricinus communis leaf disks dipped in title comp. solution with concentration <= 30 μg/cm2

Further Details (Pharmacological Data)

PDP is time-dependent; lethal concentration (LC)

Type (Pharmacological Data)

LC50

Value of Type (Pharmacological Data)

7.6 - 8.5 μg/cm2

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Bhardwaj, Anu; Tewary, Dhananjay Kumar; Kumar, Rakesh; Kumar, Vinod; Sinha, Arun Kumar; Shanker, Adarsh; Chemistry and Biodiversity; vol. 7; nb. 1; (2010); p. 168 - 177, View in Reaxys 20 of 102

Effect (Pharmacological Data)

antifeedant

Species or Test-System (Pharmacological Data)

second instar larvae of Spodoptera litura

Type (Pharmacological Data)

percent activity

Value of Type (Pharmacological Data)

> 90 percent

Bhardwaj, Anu; Tewary, Dhananjay Kumar; Kumar, Rakesh; Kumar, Vinod; Sinha, Arun Kumar; Shanker, Adarsh; Chemistry and Biodiversity; vol. 7; nb. 1; (2010); p. 168 - 177, View in Reaxys 21 of 102

Effect (Pharmacological Data)

aldehyde dehydrogenase (ALDH3) agonist

Species or Test-System (Pharmacological Data)

ALDH3 isozyme

Method (Pharmacological Data)

Example 2Plant-Derived ALDH AgonistsReagents for plant-derived compounds safrole, isosafrole, piperine, sesamin, capsaicin were purchased from Sigma-Aldrich Chemicals and dihydromethysticin was purchased from AvaChem Scientific. Piperine related compounds, Alda-101 to Alda-112, were synthesized by standard organic chemistry. All testing compounds were dissolved in dimethyl-sulfoxide (DMSO) to obtain a stock solution of 20 mM. Different recombinant ALDH isozymes with a His-epitope tag at the N-terminus were constructed, cloned and expressed in BL21 E. coli host cells according published methods (Chen et al., 2008 Science 321:1493). The bacteria were subjected to 0.5 mM IPTG induction for protein expression at 30° C. Purification of the recombinant proteins by affinity nickel columns were carried out using a standard protocol according to manufacturer's instructions (Novagen, Wis., USA).ALDH enzymatic activity was determined spectrophotometrically using purified recombinant protein (15 ug) in the reductive reaction of NAD+ to NADH at 2340 nm (Rex et al., 1985, Alcohol Clin Exp Res 9: 147). All the assays in the presence of absence of a testing compound were carried out at 25° C. in 0.1 sodium pyrophosphate buffer, pH=9.5, 2.4 mM NAD+ and 10 mM acetaldehyde or phenylacetaldehyde as a substrate.FIG. 13 depicts: Activation of ALDH3 by different compounds (50 uM) in a 3-minute kinetic assay using acetaldehyde as a substrate. Enzymatic activity is expressed in percentage using DMSO vehicle alone as the control (100percent), (n=3; **p<0.01 vs. control).FIG. 14 depicts: Activation of ALDH3 by different compounds (50 uM) in a 3-minute kinetic assay using phenylacetaldehyde as a substrate. Enzymatic activity is expressed in percentage using DMSO vehicle alone as the control (100percent), (n=3; **p<0.01 vs. control).FIG. 15 depicts: Dosage effect of safrole (Alda-89) on ALDH3 enzymatic activity using acetaldehyde as a substrate. Note that Alda-1 does not have any effect on enzymatic activity of ALDH3 isozyme, (n=3; **p<0.01 vs. control).FIG. 16 depicts: Activation of ALDH3 enzymatic activity by synthetic derivative compounds (Alda-101-Alda-112, 50 uM) of piperine using acetaldehyde as a substrate (n=3; **p<0.01 vs. control).FIG. 17 depicts: Inhibitory effect of high concentration of safrole (Alda-89, 500 uM 1000 uM) on enzymatic activity of ALDH2 isozyme using acetaldehyde as a substrate. This inhibition can be prevented and reversed by co-incubation of an ALDH2 activator Alda-1 (40 uM), (n=3; **p<0.01 vs. control).FIG. 18 depicts: 15-minute kinetic measurements of inhibitory effect of safrole (Alda-89, 1000 uM) on enzymatic activity of ALDH2 isozyme using acetaldehyde as a substrate. This inhibition can be prevented and reversed by co-incubation of an ALDH2 activator Alda-1 (40 uM). Control is DMSO vehicle alone.

Results

increase of enzyme activity (percent control) = ~300, ~475 and ~875 at 50, 100 and 500 μM, respectively (substrate: acetaldehyde), ~101 at 50 μM (substrate: phenylacetaldehyde)

Location

Page/Page column 1; 49-50

Patent; Mochly-Rosen, Daria; Chen, Che-Hong; Yang, Wenjin; US2010/113423; (2010); (A1) English, View in Reaxys 22 of 102

Effect (Pharmacological Data)

ALDH2 isozyme; inhibition of

Species or Test-System (Pharmacological Data)

ALDH2 isozyme

Method (Pharmacological Data)

Example 2Plant-Derived ALDH AgonistsReagents for plant-derived compounds safrole, isosafrole, piperine, sesamin, capsaicin were purchased from Sigma-Aldrich Chemicals

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and dihydromethysticin was purchased from AvaChem Scientific. Piperine related compounds, Alda-101 to Alda-112, were synthesized by standard organic chemistry. All testing compounds were dissolved in dimethyl-sulfoxide (DMSO) to obtain a stock solution of 20 mM. Different recombinant ALDH isozymes with a His-epitope tag at the N-terminus were constructed, cloned and expressed in BL21 E. coli host cells according published methods (Chen et al., 2008 Science 321:1493). The bacteria were subjected to 0.5 mM IPTG induction for protein expression at 30° C. Purification of the recombinant proteins by affinity nickel columns were carried out using a standard protocol according to manufacturer's instructions (Novagen, Wis., USA).ALDH enzymatic activity was determined spectrophotometrically using purified recombinant protein (15 ug) in the reductive reaction of NAD+ to NADH at 2340 nm (Rex et al., 1985, Alcohol Clin Exp Res 9: 147). All the assays in the presence of absence of a testing compound were carried out at 25° C. in 0.1 sodium pyrophosphate buffer, pH=9.5, 2.4 mM NAD+ and 10 mM acetaldehyde or phenylacetaldehyde as a substrate.FIG. 13 depicts: Activation of ALDH3 by different compounds (50 uM) in a 3-minute kinetic assay using acetaldehyde as a substrate. Enzymatic activity is expressed in percentage using DMSO vehicle alone as the control (100percent), (n=3; **p<0.01 vs. control).FIG. 14 depicts: Activation of ALDH3 by different compounds (50 uM) in a 3-minute kinetic assay using phenylacetaldehyde as a substrate. Enzymatic activity is expressed in percentage using DMSO vehicle alone as the control (100percent), (n=3; **p<0.01 vs. control).FIG. 15 depicts: Dosage effect of safrole (Alda-89) on ALDH3 enzymatic activity using acetaldehyde as a substrate. Note that Alda-1 does not have any effect on enzymatic activity of ALDH3 isozyme, (n=3; **p<0.01 vs. control).FIG. 16 depicts: Activation of ALDH3 enzymatic activity by synthetic derivative compounds (Alda-101-Alda-112, 50 uM) of piperine using acetaldehyde as a substrate (n=3; **p<0.01 vs. control).FIG. 17 depicts: Inhibitory effect of high concentration of safrole (Alda-89, 500 uM 1000 uM) on enzymatic activity of ALDH2 isozyme using acetaldehyde as a substrate. This inhibition can be prevented and reversed by co-incubation of an ALDH2 activator Alda-1 (40 uM), (n=3; **p<0.01 vs. control).FIG. 18 depicts: 15-minute kinetic measurements of inhibitory effect of safrole (Alda-89, 1000 uM) on enzymatic activity of ALDH2 isozyme using acetaldehyde as a substrate. This inhibition can be prevented and reversed by co-incubation of an ALDH2 activator Alda-1 (40 uM). Control is DMSO vehicle alone. Results

inhibition of enzyme activity (percent control) = ~55 and ~30 at 500 and 1000 μM, respectively

Location

Page/Page column 1; 49-50

Patent; Mochly-Rosen, Daria; Chen, Che-Hong; Yang, Wenjin; US2010/113423; (2010); (A1) English, View in Reaxys 23 of 102

Effect (Pharmacological Data)

ALDH2 isozyme; activation of

Species or Test-System (Pharmacological Data)

ALDH2 isozyme

Kind of Dosing (Pharmacological Data)

comcomitant administration with 40 μM of Alda-1

Method (Pharmacological Data)

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Activation of ALDH3 enzymatic activity by synthetic derivative compounds (Alda-101-Alda-112, 50 uM) of piperine using acetaldehyde as a substrate (n=3; **p<0.01 vs. control).FIG. 17 depicts: Inhibitory effect of high concentration of safrole (Alda-89, 500 uM 1000 uM) on enzymatic activity of ALDH2 isozyme using acetaldehyde as a substrate. This inhibition can be prevented and reversed by co-incubation of an ALDH2 activator Alda-1 (40 uM), (n=3; **p<0.01 vs. control).FIG. 18 depicts: 15-minute kinetic measurements of inhibitory effect of safrole (Alda-89, 1000 uM) on enzymatic activity of ALDH2 isozyme using acetaldehyde as a substrate. This inhibition can be prevented and reversed by co-incubation of an ALDH2 activator Alda-1 (40 uM). Control is DMSO vehicle alone. Results

activation of enzyme activity (percent control) = ~140 and ~125 at 500 and 1000 μM, respectively

Location

Page/Page column 1; 49-50

Patent; Mochly-Rosen, Daria; Chen, Che-Hong; Yang, Wenjin; US2010/113423; (2010); (A1) English, View in Reaxys 24 of 102

Effect (Pharmacological Data)

carcinogenicity

Species or Test-System (Pharmacological Data)

animal

Type (Pharmacological Data)

log TD50

Value of Type (Pharmacological Data)

-0.434

Location

supporting information

Toropov; Toropova; Benfenati; European Journal of Medicinal Chemistry; vol. 45; nb. 9; (2010); p. 3581 - 3587, View in Reaxys 25 of 102

Effect (Pharmacological Data)

growth; inhibition of

Species or Test-System (Pharmacological Data)

tumor breast cancer MCF-7 cells of human

Concentration (Pharmacological Data)

<= 100 μmol/l

Kind of Dosing (Pharmacological Data)

dissolved in ethanol

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 100 μmol/l

Catalan, Luis Espinoza; Villegas, Alejandro Madrid; Liber, Lautaro Taborga; Garcia, Joan Villena; Fritis, Mauricio Cuellar; Altamirano, Hector Carrasco; Journal of the Chilean Chemical Society; vol. 55; nb. 2; (2010); p. 219 - 222, View in Reaxys 26 of 102

Effect (Pharmacological Data)

growth; inhibition of

Species or Test-System (Pharmacological Data)

tumor breast cancer MDA-MB-231 cells of human

Concentration (Pharmacological Data)

<= 100 μmol/l

Kind of Dosing (Pharmacological Data)

dissolved in ethanol

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 100 μmol/l

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27 of 102

Effect (Pharmacological Data)

growth; inhibition of

Species or Test-System (Pharmacological Data)

colorectal cancer DLD-1 cells of human

Concentration (Pharmacological Data)

<= 100 μmol/l

Kind of Dosing (Pharmacological Data)

dissolved in ethanol

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 100 μmol/l

Effect (Pharmacological Data)

growth; inhibition of

Species or Test-System (Pharmacological Data)

dermal fibroblast DHF cells of human

Concentration (Pharmacological Data)

<= 100 μmol/l

Kind of Dosing (Pharmacological Data)

dissolved in ethanol

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 100 μmol/l

Effect (Pharmacological Data)

AA-induced platelet aggregation; inhibition of

Species or Test-System (Pharmacological Data)

venous blood of human

Concentration (Pharmacological Data)

12.5 - 100 μg/ml

Kind of Dosing (Pharmacological Data)

dissolved in DMSO

Further Details (Pharmacological Data)

AA: arachidonic acid; inhibitory concentration (IC)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

33.3 μg/ml

Moharam, Bushra Abdulkarim; Jantan, Ibrahim; Ahmad, Fasihuddin Bin; Jalil, Juriyati; Molecules; vol. 15; nb. 8; (2010); p. 5124 - 5138, View in Reaxys 30 of 102

Effect (Pharmacological Data)

AA-induced platelet aggregation; inhibition of

Species or Test-System (Pharmacological Data)

venous blood of human

Concentration (Pharmacological Data)

12.5 - 100 μg/ml

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Kind of Dosing (Pharmacological Data)

dissolved in DMSO

Further Details (Pharmacological Data)

AA: arachidonic acid

Type (Pharmacological Data)

inhibition

Value of Type (Pharmacological Data)

10.53 - 93.4 percent

Moharam, Bushra Abdulkarim; Jantan, Ibrahim; Ahmad, Fasihuddin Bin; Jalil, Juriyati; Molecules; vol. 15; nb. 8; (2010); p. 5124 - 5138, View in Reaxys 31 of 102

Effect (Pharmacological Data)

ADP-induced platelet aggregation; inhibition of

Species or Test-System (Pharmacological Data)

venous blood of human

Concentration (Pharmacological Data)

12.5 - 100 μg/ml

Kind of Dosing (Pharmacological Data)

dissolved in DMSO

Further Details (Pharmacological Data)

ADP: adenosine diphosphate; inhibitory concentration (IC)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

28.2 μg/ml

Moharam, Bushra Abdulkarim; Jantan, Ibrahim; Ahmad, Fasihuddin Bin; Jalil, Juriyati; Molecules; vol. 15; nb. 8; (2010); p. 5124 - 5138, View in Reaxys 32 of 102

Effect (Pharmacological Data)

ADP-induced platelet aggregation; inhibition of

Species or Test-System (Pharmacological Data)

venous blood of human

Concentration (Pharmacological Data)

12.5 - 100 μg/ml

Kind of Dosing (Pharmacological Data)

dissolved in DMSO

Further Details (Pharmacological Data)

ADP: adenosine diphosphate

Type (Pharmacological Data)

inhibition

Value of Type (Pharmacological Data)

20.34 - 97.2 percent

Moharam, Bushra Abdulkarim; Jantan, Ibrahim; Ahmad, Fasihuddin Bin; Jalil, Juriyati; Molecules; vol. 15; nb. 8; (2010); p. 5124 - 5138, View in Reaxys 33 of 102

Effect (Pharmacological Data)

receptor binding affinity

Species or Test-System (Pharmacological Data)

platelets of rabbit

Concentration (Pharmacological Data)

18.2 μg/ml

Further Details (Pharmacological Data)

PAF: platelet activating factor (1-O-octadecyl-2-acetyl-sn-glycero-3-phosphocholine); [3H]PAF was used as radioligand; IC50 = 2.8 μg/ml for cedrol; inhibition related to: PAF receptor

Type (Pharmacological Data)

inhibition

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Value of Type (Pharmacological Data)

30.8 percent

Moharam, Bushra Abdulkarim; Jantan, Ibrahim; Ahmad, Fasihuddin Bin; Jalil, Juriyati; Molecules; vol. 15; nb. 8; (2010); p. 5124 - 5138, View in Reaxys 34 of 102

Effect (Pharmacological Data)

receptor binding affinity

Species or Test-System (Pharmacological Data)

platelets of rabbit

Concentration (Pharmacological Data)

18.2 μg/ml

Further Details (Pharmacological Data)

PAF: platelet activating factor (1-O-octadecyl-2-acetyl-sn-glycero-3-phosphocholine); [3H]PAF was used as radioligand; IC50 = 2.8 μg/ml for cedrol

Results

molecular target: PAF receptor

Moharam, Bushra Abdulkarim; Jantan, Ibrahim; Ahmad, Fasihuddin Bin; Jalil, Juriyati; Molecules; vol. 15; nb. 8; (2010); p. 5124 - 5138, View in Reaxys 35 of 102

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or Test-System (Pharmacological Data)

cytochrome P450 1A2

Kind of Dosing (Pharmacological Data)

dissolved in methanol

Further Details (Pharmacological Data)

inhibitory concentration (IC)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

22.1 μmol/l

Huang, Yu-Ting; Onose, Jun-Ichi; Abe, Naoki; Yoshikawa, Kunie; Bioscience, Biotechnology and Biochemistry; vol. 73; nb. 4; (2009); p. 855 - 860, View in Reaxys 36 of 102

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or Test-System (Pharmacological Data)

cytochrome P450 1A2

Kind of Dosing (Pharmacological Data)

dissolved in methanol

Results

molecular target: cytochrome P450 1A2

Huang, Yu-Ting; Onose, Jun-Ichi; Abe, Naoki; Yoshikawa, Kunie; Bioscience, Biotechnology and Biochemistry; vol. 73; nb. 4; (2009); p. 855 - 860, View in Reaxys 37 of 102

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or Test-System (Pharmacological Data)

cytochrome P450 3A4

Kind of Dosing (Pharmacological Data)

dissolved in methanol

Further Details (Pharmacological Data)

inhibitory concentration (IC)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

40.2 μmol/l

Huang, Yu-Ting; Onose, Jun-Ichi; Abe, Naoki; Yoshikawa, Kunie; Bioscience, Biotechnology and Biochemistry; vol. 73; nb. 4; (2009); p. 855 - 860, View in Reaxys

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38 of 102

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or Test-System (Pharmacological Data)

cytochrome P450 3A4

Kind of Dosing (Pharmacological Data)

dissolved in methanol

Results

molecular target: cytochrome P450 3A4

Huang, Yu-Ting; Onose, Jun-Ichi; Abe, Naoki; Yoshikawa, Kunie; Bioscience, Biotechnology and Biochemistry; vol. 73; nb. 4; (2009); p. 855 - 860, View in Reaxys 39 of 102

Effect (Pharmacological Data)

peroxisome proliferator-activated receptor gamma (PPARγ); binding affinity

Species or Test-System (Pharmacological Data)

peroxisome proliferator-activated receptor (PPAR)-γ-ligand binding domain (LBD)

Method (Pharmacological Data)

Example 1PPAR-Gamma Assay and PPAR-Gamma Binding Activity1.1 Extraction and Preparation of the Plants/Plant Powders100 mg dry powder of plants, herbs or spices was suspended in 1 ml DMSO for 24 h at room temperature. The suspension was stirred on a magnetic stirrer. After 24 h the extract was clarified by centrifugation for 1 h at 13.000 rpm. The clear supernatant was further diluted by DMSO and then binding to PPARγwas tested by Peroxisome Proliferator-Activated Receptor-gamma Competitor Assay Kit, Green (Invitrogen, Carlsbad, Calif.).1.2 Polar Screen PPAR Competitive AssayPPAR-gamma Competitive assay was performed according to manufacturer's instructions as described in the PolarScreen.(TM). PPAR Competitor Assay, Green Protocol (839-0412498 060904). PPAR-gamma-LBD and the fluorescent PPAR-gamma ligand (Fluormone.(TM). PPAR Green) form a PPAR-gamma-LBD/Fluormone.(TM). PPAR-gamma Green complex which has a high polarization value. If a competitor of PPAR-gamma is added the fluorescent ligand is displaced. This causes that the Fluoromone is free in solution and tumbles rapidly during its fluorescence lifetime which results in a low polarisation value. Substances which do not compete will not displace the fluorescent ligand from the complex so that the high polarisation value remains.1 μl of test compounds, which was dissolved and diluted in DMSO, was transferred into a microwell plate. Complete screening buffer was prepared by addition of 0.5 μl DTT (1M) to 1 ml PPAR Green Screening Buffer. 19 μl of this buffer was added to each well of microwell plate. The PPAR-LBD/Fluoromone Green complex solution was prepared by addition of 16 μl Fluoromone PPAR Green solution (500 nM) per 1.6 ml and 2 μl PPAR-gamma-Ligand binding domain (1.56 mg/ml) per 1.6 ml to complete screening buffer. 20 μl of this solution was added to each well. The plate is covered to protect the reagents from light and incubated for two hours at room temperature. Fluorescence polarization was measured at excitation wavelength 485 nm and emission 535 nm with Tecan Genios Pro plate reader (Tecan, Austria).1.3 Curve FittingData of the ligand binding assay were calculated in the following way: Polarization values were plotted against the concentration of test compound. The curve was fitted using a logistic dose-response model from Table Curve 2D software (Jandel Scientific). The used function was:The parameter a equals the baseline, b is the difference between the plateau of the curve and the baseline and c is the transition center of the curve which is the concentration that causes 50percent of efficiency (ligand potency). d gives the transition zone and is a measure for positive or negative co-operatively.The concentration of the test compound that results in a half-maximal shift in polarization value is the EC50 value of the test compound. This value serves as measure of relative binding affinity to PPAR-gamma. Fitted curves are depicted in FIGS. 1 to 4.

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

2.25 mmol/l

Location

Page/Page column 5-6

Patent; Melbrosin International Produktions- und Vertriebs GesmbH and Co KG; US2008/131534; (2008); (A1) English, View in Reaxys 40 of 102

Effect (Pharmacological Data)

calcium accumulation; effect on

Species or Test-System (Pharmacological Data)

osteoblast MC3T3-E1 cells (ATCC CRL-2593)

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Method (Pharmacological Data)

Test Example 1: The influence of the seeds extract of Myristica fragrans on the calcium formation in the osteoblast(1-1) Culture and differentiation induction of osteoblast MC3T3E1 subclone 4 (ATCC CRL-2593) was used as osteoblast cells, and medium and other materials used in cell culture were purchased from HyClone Laboratories Inc.. The osteoblast cells were cultured in an α-MEM medium supplemented with 10percent FBS, and the medium was replaced wih a fresh medium every 3 days. At 70percent confluency, the cultured cells were removed from the culture plate by using trypsin, and 1 x 104 cells were transferred to each well of a 48-well plate. At a confluency of 95percent and more, the medium was changed to a differentiation-inducing medium (α-MEM containing 10percent FBS, 50 μg/m. ascorbic acid and 10 mM β-glycerophosphate). Cells were then cultured while replacing the medium with a fresh medium every 3 days. 0.1, 1 and 10 βglml of the seeds extract of Myristica fragrans of Example 1, the ethylacetate fraction, n-butanol fraction and water fraction were each added thereto (treatment).(1-2) Staining and quantitation of calcium formed in the osteoblast After 21 days of the treatment, the cells were washed with PBS, reacted with an alizarin red S staining solution (0.1368 g in 10 ml water, pH 4.2), and washed with water to detect the presence of accumulated calcium which was stained (Fig. 3A). The accumulated calcium was extracted with IN HCl, and quantified using Calcium C kit (Wako, Japan) (Fig. 3B).As shown in Fig. 3 A, when 10 μg/m-β of the methanol extract of Myristica fragrans, ethylacetate fraction and water fraction, respectively, were used to treat cells, increased amounts of stained calcium were observed as compared with the non-treated control group. Further, as shown in Fig. 3B, the treated groups formed more calcium as compared with the non-treated control group in the view of statistical significance: the statistical significance was tested by t-test (* p<0.01, ** pO.OOl) based on the mean value of the control groups of 2.75 mg/dL.; Test Example 2: Analysis of calcium formation in the osteoblast by the compounds isolated from the seeds extract of Myristica fragransThe effects of the compounds of Examples 2 to 9 isolated from the seeds extract of Myristica fi'agrans on the calcium formation in cases of osteoblast were tested as described in Test Example 1.As shown in Fig. 4, the treatment with 10 μM machilin A showed the highest amount of accumulated calcium, while the treatments with 5 μM macelignan, machilin F, nectandrin B, safrole, licarin A, licarin B, myristagenol A and meso-dihydroguaiaretic acid were each most effective in obtaining the highest amount of accumulated calcium in the osteoblast cases under test.Consequently, the amounts of calcium formation in the osteoblast case induced by the compounds of Examples 2 to 9 were 15 to 100 times higher than that of the non-treated control group.

Results

title compound at 5 μmol/l was most effective in obtaining the highest amount of accumulated calcium in the osteoblast cases; figure is given

Location

Page/Page column 14; 15; sheet 5

Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; WO2008/96998; (2008); (A1) English, View in Reaxys 41 of 102

Effect (Pharmacological Data)

antibacterial

Species or Test-System (Pharmacological Data)

KCCM-10639 of Bacillus subtilis

Method (Pharmacological Data)

Example 3Examination of Resistance to Prior Fungicides (Agricultural Chemicals)(1) Experimental Method(i) N.A (nutrient broth agar) medium was prepared 2-3 days before the experiment.(ii) Sterilized water (distilled water) was prepared. Then, agricultural chemicals were dissolved in sterilized water (distilled water) in recommended amounts.(iii) 100 μl of the solution of the step (ii) was absorbed into filter paper, followed by drying. Then, the filter paper was placed on 100 μl of smear medium. Then, the medium was sealed and incubated at 25° C. for 2 days. As a control group, distilled water was used.(iv) The test results were observed.(v) Whether a clear zone (growth-inhibitory zone) was produced around the paper disc was determined on the basis of whether the bacteria grew.(vi) When the clear zone was not produced, the antagonistic strain was determined to have resistance to the agricultural chemicals, and when the clear zone was produced, the antagonistic strain was determined to be influenced by the agricultural chemicals. In this case, the diameter of the clear zone was measured and recorded.(2) ResultsThe novel strains KCCM 10639 and KCCM 10640 showed resistance to the prior fungicides. The prior fungicides and the resistance of the novel strains to the fungicides are shown in Table 1.

Results

middle-strong resistance to title compound was observed (100 μl/100 ml comcentration)

Location

Page/Page column 3-4

Comment (Pharmacological Data)

potential area of application: agro

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Patent; Kyu Jin Yum; US2008/267937; (2008); (A1) English, View in Reaxys 42 of 102

Effect (Pharmacological Data)

antibacterial

Species or Test-System (Pharmacological Data)

KCCM-10640 of Bacillus subtilis

Method (Pharmacological Data)

Results

middle-strong resistance to title compound was observed (100 μl/100 ml comcentration)

Location

Page/Page column 3-4

Comment (Pharmacological Data)

potential area of application: agro

Patent; Kyu Jin Yum; US2008/267937; (2008); (A1) English, View in Reaxys 43 of 102

Effect (Pharmacological Data)

haemolytic

Species or Test-System (Pharmacological Data)

mouse erythrocytes

Concentration (Pharmacological Data)

10 - 200 mg/l

Method (Pharmacological Data)

title comp. incubated with test cells in 0.85 percent saline containing 10 mmol/l CaCl2 at room temp. for 30 min and centrifuged; liberated hemoglobin quantified in supernatant spectrophotometrically at 540 nm

Further Details (Pharmacological Data)

Triton X-100 (20 μl of 0.1 percent solution in 0.85 percent saline) as positive control

Results

title comp. exhibited hemolytic activity only at highest tested concentration 200 μg/ml

Moreira, Diogo Rodrigo de Magalhaes; Lima Leite, Ana Cristina; Pinheiro Ferreira, Paulo Michel; da Costa, Patricia Marcal; Costa Lotufo, Leticia Veras; de Moraes, Manoel Odorico; Brondani, Dalci Jose; do O Pessoa, Claudia; European Journal of Medicinal Chemistry; vol. 42; nb. 3; (2007); p. 351 - 357, View in Reaxys 44 of 102

Effect (Pharmacological Data)

cytotoxicity

Species or Test-System (Pharmacological Data)

human myeloblastic leukemia HL-60 cells

Concentration (Pharmacological Data)

0.39 - 25 mg/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Method (Pharmacological Data)

MTT assay; title comp. incubated with test cells in RPMI-1640 supplemented with 10 percent fetal calf serum and antibiotics at 37 deg C for 72 h; medium replaced by fresh one, MTT added; 3 h later absorbance of formazan product at 590 nm measured

Further Details (Pharmacological Data)

doxorubicin with IC50 0.03 μmol/l as positive control

Type (Pharmacological Data)

IC50

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Value of Type (Pharmacological Data)

104.5 μmol/l

Effect (Pharmacological Data)

cytotoxicity

Species or Test-System (Pharmacological Data)

human colon carcinoma HCT-8 cells

Concentration (Pharmacological Data)

0.39 - 25 mg/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Method (Pharmacological Data)

Further Details (Pharmacological Data)

doxorubicin with IC50 0.03 μmol/l as positive control

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

36.1 μmol/l

Effect (Pharmacological Data)

cytotoxicity

Species or Test-System (Pharmacological Data)

human breast cancer MDA-MB-435 cells

Concentration (Pharmacological Data)

0.39 - 25 mg/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Method (Pharmacological Data)

Further Details (Pharmacological Data)

doxorubicin with IC50 0.83 μmol/l as positive control

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

104.7 μmol/l

Effect (Pharmacological Data)

cytotoxicity

Species or Test-System (Pharmacological Data)

human glyoblastoma SF-295 cells

Concentration (Pharmacological Data)

0.39 - 25 mg/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

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Method (Pharmacological Data)

Further Details (Pharmacological Data)

doxorubicin with IC50 0.42 μmol/l as positive control

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

32.6 μmol/l

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

recombinant rat hepatoma H4L1.1c4 cells

Concentration (Pharmacological Data)

10 μmol/l

Method (Pharmacological Data)

AhR-regulated gene expression analyzed by luciferase reporter gene assay; cells transfected with DRE-driven firefly luciferase reporter gene incubated with title comp. for 4 h at 37 deg C; luciferase activity measured with luminometer

Further Details (Pharmacological Data)

control: dimethylsulfoxide; TCDD: 2,3,7,8-tetrachlorodibenzo-p-dioxin; DRE: dioxin-response element; AhR: aryl hydrocarbon receptor; result expressed as percent of induction by TCDD (1 nM)

Comment (Pharmacological Data)

No effect

Hu, Wenyue; Sorrentino, Claudio; Denison, Michael S.; Kolaja, Kyle; Fielden, Mark R.; Molecular Pharmacology; vol. 71; nb. 6; (2007); p. 1475 - 1486, View in Reaxys 49 of 102

Effect (Pharmacological Data)

DNA adducts; formation of

Species or Test-System (Pharmacological Data)

human hepatoma HepG2 cells

Concentration (Pharmacological Data)

50 - 450 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in dimethyl sulfoxide

Method (Pharmacological Data)

cells incubated with title comp. for 24 h; DNA adducts formation analyzed by dinucleotide/ monophosphate version of <32P>-postlabeling assay and multidirectional ion-exchanged thin-layer chromatography

Results

title comp. dose-dependently leads to DNA adduct formation; two types of DNA adducts were detected: major and minor (3' or 1'-carbons of side chain of title comp. binds to guanine, resp.) in the ratio of 3.1

Zhou, Guo-Dong; Moorthy, Bhagavatula; Bi, Jia; Donnelly, Kirby C.; Randerath, Kurt; Environmental and Molecular Mutagenesis; vol. 48; nb. 9; (2007); p. 715 - 721, View in Reaxys 50 of 102

Effect (Pharmacological Data)

calcium homeostasis; effect on

Species or Test-System (Pharmacological Data)

human OC2 oral cancer cells

Concentration (Pharmacological Data)

Ca. 150 - 850 μmol/l

Kind of Dosing (Pharmacological Data)

dissolved in ethanol

Method (Pharmacological Data)

fura-2/acetoxy methyl-loaded cells in Ca(2+)-containing medium exposed to title comp.; fluorescence monitored at 1-s intervals (excitation at 340/380 nm; emission at 510 nm)

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Further Details (Pharmacological Data)

further investigation on mechanism with Ca(2+) entry blockers, endoplasmic reticulum Ca(2+) pump inhibitor (thapsigargin), phospholipase C-depen. agonist (bradykinin), protein kinase C activator (phorbol 12-myristate 13-acetate) or inhibitor (GF109203X)

Results

title comp. dose-dependently (starting at 325 μmol/l) increased intracellular Ca(2+) levels by causing release of stored Ca(2+) from endoplasmic reticulum in a phospholipase C-, protein kinase C-independent fashion via nifedipine-sensitive Ca(2+) entry

Huang, Jong-Khing; Huang, Chun-Jen; Chen, Wei-Chuan; Liu, Shiuh-Inn; Hsu, Shu-Shong; Chang, Hong-Tai; Tseng, Li-Ling; Chou, Chiang-Ting; Chang, Chih-Hung; Jan, Chung-Ren; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 372; nb. 1; (2005); p. 88 - 94, View in Reaxys 51 of 102

Effect (Pharmacological Data)

growth stimulation

Species or Test-System (Pharmacological Data)

human OC2 oral cancer cells

Concentration (Pharmacological Data)

1 - 1 μmol/l

Kind of Dosing (Pharmacological Data)

dissolved in ethanol

Method (Pharmacological Data)

cells in serum-free medium incubated with title comp. for 16 h; cell viability analyzed using WST-1 reagent

Further Details (Pharmacological Data)

further investigation on mechanism of action with intracellular calcium chelator (BARTA)

Results

1 μmol/l dose of title comp. had no effect; at 10-1000 μmol/l title comp. dose-independently induced significant 50-70 percent increase in cell proliferation in a Ca(2+)-independent manner

Effect (Pharmacological Data)

farnesoid X-activated receptor (FXR)-mediated transcription; activation of

Species or Test-System (Pharmacological Data)

chinese hamster ovary (CHO K1) cells transfected with FXR DNA of rat

Method (Pharmacological Data)

Example 1 Materials and Methods [0177] A. Cell Growth Conditions [0178] Chinese hamster ovary (CHO K1) cells were grown in Dulbecco's modified Eagle medium: nutrient mixture F-12 (1:1) containing 5percent fetal bovine serum and supplemented with 50 u/ml penicillin, and 50 μg/ml streptomycin (Life Technologies) in a water-jacketed incubator held at 37° C. and maintained with a 5percent CO2 atmosphere. [0179] B. Chemicals [0180] Chemicals were purchased from Sigma-Aldrich Chemical Company (St. Louis, Mo.) unless noted. Plant oils were manufactured by Aura Cacia (Weaverville, Calif.). Juvocimene was synthesized as described (Mestres, R. and E. Munoz, 1996, Synthetic Comm., 26:1309-1319). Myristicin, apiole, bergamotin, tangeretin, bisabolol, and cucurbitacin were obtained from Indofine Chemical Company (Somerville, N.J.). Methyleugenol was provided by the Batelle Chemical Company (Columbus, Ohio). Man-made insecticides were purchased from Chem Service (West Chester, Pa.). The precocene-like suicide substrate 3,4-dimethoxyisopentenylphenol was prepared as described Bowers, W. S., et al., 1976, Science, 217:647-648) except that a 3,4-dimethoxylated reactant was used. [0181] C. Transfection Assay [0182] The transcriptional assay utilized for the study of EcR potentiation by JH (FIGS. 2-5) was modified from the assay described by Forman et al., (Forman, B. M., et al., 1995, Cell 81, 687-695) as described below. Cells were seeded in 6-well polypropylene culture plates (Falcon) with 105 cells per well on the day prior to transfection. Transfection was subsequently performed using either calcium phosphate (Kitareewan, S., et al., 1996, Mol. Biol. Cell, 7:1153-1196) or a GenePorter reagent (Gene Therapy Systems, Inc; San Diego, Calif.) following manufacturer's protocols. Each well received 1.25 μg of (EcRE)5-ΔMTV-CAT (five copies of the hsp27 EcRE inserted into an mouse mammary tumor virus (MTV) promoter upstream of the chloramphenicol acetyltransferase (CAT) gene) or (EcRE)5-ΔMTV-LUC (the same promoter attached to firefly luciferase), 1.25 μg of pCH 111(SV40 early promoter linked to the β-galactosidase gene) to normalize CAT activity, and 0.25 μg of each expression plasmid (EcR, FXR, RXR, USP) that was tested. The cells were incubated with plasmid DNA for seven hours and then washed with 1.x.PBS. Muristerone A (murA; Alexis Biochemicals) or 20-hydroxyecdysone (20E; Sigma) dissolved in ethanol to a concentration of 10 mM was diluted as necessary to the final assay concentration (FAC) in 2 ml of fresh incubation medium that was then applied to the cells. Similarly, JHIII (Sigma) was dissolved in dimethyl sulfoxide (DMSO) to

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a concentration of 80 μM and diluted into the incubation medium to its final assay concentration (20, 40, 80, 160 μM). For experiments to test the effects of chenodeoxycholate (CDCA, Sigma) on FXR and EcR, CDCA was dissolved in DMSO at 20 mM and diluted in the culture medium to a final concentration of 20 μM. A corresponding volume of ethanol and DMSO were added to control cells for all experiments. For all experiments, the cells were allowed to incubate with the medium for 24 hours before collection and cell lysates were prepared by described methods (Kitareewan et al., 1996). Both β-galactosidase and CAT reporter activity were measured based on previously used methods (Kitareewan et al, 1996). Luciferase assays using luciferrin followed the specifications of the manufacturer. [0183] Transcriptional activity, measured as 14C-chloramphenicol counts (for measuring CAT activity) or relative luciferase activity (RLU) was quantified for each cell lysate. The counts were then normalized by adjusting for differences in β-galactosidase activity, since β-galactosidase expression is controlled by a constitutive promoter and provides an estimate of cell mass. Data were normalized as fold-induction based on differences in reporter gene activity between h Results

title compound increases farnesoid X-activated receptor (FXR)-mediated transcription with ~1.5 fold-induction or does not effect on farnesoid X-activated receptor (FXR)-mediated transcription; concentration dependent; see Fig.8E

Location

Page/Page column 14-15; 19-20; 24-25

Patent; Henrich, Vincent C.; Weinberger, Cary Alan; US2005/49230; (2005); (A1) English, View in Reaxys 53 of 102

Effect (Pharmacological Data)

antiaggregant

Species or Test-System (Pharmacological Data)

rabbit platelets

Concentration (Pharmacological Data)

100 mg/l

Method (Pharmacological Data)

washed platelets were preincubated with title comp. at 37 deg C for 3 min; then plateletactivating factor (PAF, 2 ng/ml) added; platelet aggregation determined by anti-platelet aggregation test

Further Details (Pharmacological Data)

negative control: DMSO

Results

title comp. insignificantly inhibited PAF-induced platelet aggregation from 93.0 percent in control to 91.7 percent

Chen, Yu-Chang; Chen, Jih-Jung; Chang, Ya-Ling; Teng, Che-Ming; Lin, Wei-Yu; Wu, Chin-Chung; Chen, IhSheng; Planta Medica; vol. 70; nb. 2; (2004); p. 174 - 177, View in Reaxys 54 of 102

Effect (Pharmacological Data)

antiaggregant

Species or Test-System (Pharmacological Data)

rabbit platelets

Concentration (Pharmacological Data)

20 - 100 mg/l

Method (Pharmacological Data)

washed platelets were preincubated with title comp. at 37 deg C for 3 min; then collagen (Col, 10 μg/ml) added; platelet aggregation determined by anti-platelet aggregation test

Further Details (Pharmacological Data)

positive control: aspirin; negative control: DMSO

Results

title comp. significantly dose-dependently inhibited Col-induced platelet aggregation (from 89.3 percent in control to 84.9-17.0 percent at 20-100 μg/ml, resp.); title comp. was more potent than aspirin (table)

Chen, Yu-Chang; Chen, Jih-Jung; Chang, Ya-Ling; Teng, Che-Ming; Lin, Wei-Yu; Wu, Chin-Chung; Chen, IhSheng; Planta Medica; vol. 70; nb. 2; (2004); p. 174 - 177, View in Reaxys 55 of 102

Effect (Pharmacological Data)

antiaggregant

Species or Test-System (Pharmacological Data)

rabbit platelets

Concentration (Pharmacological Data)

20 - 100 mg/l

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Method (Pharmacological Data)

platelets were preincubated with title comp. at 37 deg C for 3 min; then arachidonic acid (AA, 100 μmol/l) added; platelet aggregation determined by anti-platelet aggregation test

Further Details (Pharmacological Data)

positive control: aspirin; negative control: DMSO

Results

title comp. dose-dependently (significantly at 50-100 μg/ml) inhibited AA-induced platelet aggregation (from 87.8 percent aggregation in control to 84.6-20.9 percent at 20-100 μg/ml, resp.); title comp. was less potent than aspirin

Chen, Yu-Chang; Chen, Jih-Jung; Chang, Ya-Ling; Teng, Che-Ming; Lin, Wei-Yu; Wu, Chin-Chung; Chen, IhSheng; Planta Medica; vol. 70; nb. 2; (2004); p. 174 - 177, View in Reaxys 56 of 102

Effect (Pharmacological Data)

antiaggregant

Species or Test-System (Pharmacological Data)

rabbit platelets

Concentration (Pharmacological Data)

100 mg/l

Method (Pharmacological Data)

after 3-min preincubation of washed platelets with title comp. at 37 deg C, thrombin (0.1 U/ml) added; platelet aggregation determined by anti-platelet aggregation test

Further Details (Pharmacological Data)

negative control: DMSO

Comment (Pharmacological Data)

No effect

Chen, Yu-Chang; Chen, Jih-Jung; Chang, Ya-Ling; Teng, Che-Ming; Lin, Wei-Yu; Wu, Chin-Chung; Chen, IhSheng; Planta Medica; vol. 70; nb. 2; (2004); p. 174 - 177, View in Reaxys 57 of 102

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

electric eel acetylcholinesterase

Concentration (Pharmacological Data)

0.5 mmol/l

Kind of Dosing (Pharmacological Data)

dissolved in 5 percent ethanol

Method (Pharmacological Data)

enzyme incubated with ATCI in sodium phosphate buffer for 15 min at 25 deg C, pH 8.0 in presence of title comp.; hydrolysis of ATCI monitored by formation of yellow 5-thio-2-nitrobenzoate at 412 nm

Further Details (Pharmacological Data)

positive control: physostigmine; ATCI: acetylthiocholine iodide

Comment (Pharmacological Data)

No effect

Gilani, Anwar H.; Ghayur, M. Nabeel; Saify, Zafar S.; Ahmed, Shahida P.; Choudhary, M. Iqbal; Khalid, Asaad; Life Sciences; vol. 75; nb. 20; (2004); p. 2377 - 2389, View in Reaxys 58 of 102

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

30 - 300 mg/kg

Kind of Dosing (Pharmacological Data)

title comp. dissolved in Mazola corn oil at 30, 75, 150, 300 mg/kg body weight

Method (Pharmacological Data)

4 adult rats/group; urine samples collected for 0-24 h after administration; centrifugated at 10,000 g for 20 min; glucuronidase used to cleave urinary conjugates; incubated at 37 deg C for 16 h; extracted; analyzed using reverse-phased isocratic HPLC

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Further Details (Pharmacological Data)

1 N HCl hydrolysis under nitrogen gas was used to accomplish the deconjugation of metabolites; control group administered Mazola corn oil only

Results

major urinary metabolite was dihydroxychavicol

Metabolite XRN (Pharmacological Data)

1366759; 1937030

Metabolite (Pharmacological Data)

4-allylguaiacol; 1-allyl-3,4-dihydroxybenzene

Chang; Ko; Lin; Hsieh; Archives of Environmental Contamination and Toxicology; vol. 43; nb. 4; (2002); p. 432 437, View in Reaxys 59 of 102

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

human

Sex

male

Route of Application

peroral

Kind of Dosing (Pharmacological Data)

during habitual TBQ chewing, from 2 to 100 TBQ per day

Method (Pharmacological Data)

153 spot urine samples collected by public health study from south of Taiwan; centrifugated at 10,000 g for 20 min; glucuronidase used to cleave urinary conjugates; incubated at 37 deg C for 16 h; extracted; analyzed using reverse-phased isocratic HPLC

Further Details (Pharmacological Data)

year of habitual TBQ chewing 1-61; starting age of chewing: 14-61 years; TBQ: Taiwanese betel quid; 1 N HCl hydrolysis under nitrogen gas was used for deconjugation of metabolites; control group: without habitual TBQ chewing

Results

major urinary metabolite was dihydroxychavicol

Metabolite XRN (Pharmacological Data)

1366759; 1937030

Metabolite (Pharmacological Data)

4-allylguaiacol; 1-allyl-3,4-dihydroxybenzene

Chang; Ko; Lin; Hsieh; Archives of Environmental Contamination and Toxicology; vol. 43; nb. 4; (2002); p. 432 437, View in Reaxys 60 of 102

Effect (Pharmacological Data)

biotransformation

Endpoint of Effect (Pharmacological Data)

GSH-conjugate formation

Species or Test-System (Pharmacological Data)

rat liver microsomes

Kind of Dosing (Pharmacological Data)

title comp. admin. as a part of essential oil of Sassafras albidum (Nutt.)

Method (Pharmacological Data)

title comp. in botanical extract stock solution mixed with GSH, NADPH and flow injected into pulsed ultrafiltration chamber (methylcellulose membrane, male Sprague-Dawley rat microsomes in phosphate buffer); ultrafiltrate collected over 30 min; LC-MS-MS

Further Details (Pharmacological Data)

control to essential oil of sassafras and NADPH without GSH or with GSH, but without rat liver microsomes; screening for formation of GSH-conjugated metabolites of title comp.; GSH: glutathion

Results

sign. formation both title comp.- and it metabolite-GSH conjugates; detection of title comp. GSH-conjugated metabolites formation during pulsed ultrafiltration experiments used as method of screening botanical extracts for title comp. or its metabolites

Metabolite XRN (Pharmacological Data)

1937030

Metabolite (Pharmacological Data)

1-allyl-3,4-dihydroxybenzene

Johnson; Bolton; Van Breemen; Chemical Research in Toxicology; vol. 14; nb. 11; (2001); p. 1546 - 1551, View in Reaxys

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61 of 102

Effect (Pharmacological Data)

genetic toxicity in vitro

Species or Test-System (Pharmacological Data)

human hepatoma Hep G2 cells

Concentration (Pharmacological Data)

1000 - 6700 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Method (Pharmacological Data)

in vitro; cells cultured in DMEM for 24 h in Petri dishes; exposed to title comp. for 24 h; cells trypsinized; single cell gel electrophoresis assay; DNA migration

Results

dose-dependent induction of DNA migration; lowest conc. causing signif. positive effect: 40000 μM

Uhl, Maria; Helma, Christoph; Knasmueller, Siegfried; Mutation Research - Genetic Toxicology and Environmental Mutagenesis; vol. 468; nb. 2; (2000); p. 213 - 225, View in Reaxys 62 of 102

Effect (Pharmacological Data)

antifungal

Species or Test-System (Pharmacological Data)

E. flocossum C 114

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

> 50 mg/l

Effect (Pharmacological Data)

antifungal

Species or Test-System (Pharmacological Data)

T. rubrum C 113

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

> 50 mg/l

Effect (Pharmacological Data)

antifungal

Species or Test-System (Pharmacological Data)

T. mentagrophytes ATCC 9972

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

> 50 mg/l

Effect (Pharmacological Data)

antifungal

Species or Test-System (Pharmacological Data)

M. gypseum C 115

Type (Pharmacological Data)

MIC

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Value of Type (Pharmacological Data)

> 50 mg/l

Effect (Pharmacological Data)

antifungal

Species or Test-System (Pharmacological Data)

M. canis C 112

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

> 50 mg/l

Effect (Pharmacological Data)

genetic toxicity in vitro

Endpoint of Effect (Pharmacological Data)

MN frequency

Species or Test-System (Pharmacological Data)

3.7.2C mouse lymphoma cells L5178Y TK+/- clone

Concentration (Pharmacological Data)

50.69 - 405.5 mg/l

Kind of Dosing (Pharmacological Data)

50.69, 101.37, 202.75, and 405.50 μg/ml in DMSO

Exposure Period (Pharmacological Data)

Method (Pharmacological Data)

metabolic activation; cells were incubated with title comp. in the presence of S9 mix in FM0 at 37 deg C for 4 h; then cells were washed and harvested after 24-hr recovery period; micromethod for the in vitro micronucleus assay

Further Details (Pharmacological Data)

estimation of the number of micronuclei (MN) per 1000 mononucleated cells (MNC); S9 mix was obtained from liver of rats activated with Arochlor 1254; Fischer medium (FM0)

Results

sign. increase in MN frequency at 202.75 μg/ml; at 405.50 μg/ml evaluation was impossible

Nesslany, Fabrice; Marzin, Daniel; Mutagenesis; vol. 14; nb. 4; (1999); p. 403 - 410, View in Reaxys 68 of 102

Effect (Pharmacological Data)

cytotoxicity

Endpoint of Effect (Pharmacological Data)

MTT incorporation

Species or Test-System (Pharmacological Data)

3.7.2C mouse lymphoma cells L5178Y TK+/- clone

Concentration (Pharmacological Data)

50.69 - 405.5 mg/l

Kind of Dosing (Pharmacological Data)

50.69, 101.37, 202.75, and 405.50 μg/ml in DMSO

Exposure Period (Pharmacological Data)

Method (Pharmacological Data)

metabolic activation; cells were incubated with title comp. in the presence of S9 mix in FM0 at 37 deg C for 4 h; MTT cytotoxicity test after 24-hr recovery period

Further Details (Pharmacological Data)

estimation of title comp. cytotoxicity according to 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) incorporation; S9 mix was obtained from liver of rats activated with Arochlor 1254; Fischer medium (FM0)

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Results

dose-dependently reduction of cell viability up to 0 percent at the highest dose

Nesslany, Fabrice; Marzin, Daniel; Mutagenesis; vol. 14; nb. 4; (1999); p. 403 - 410, View in Reaxys 69 of 102

Effect (Pharmacological Data)

oxidative stress

Endpoint of Effect (Pharmacological Data)

LHPs, 8-OH-dG levels in liver; serum ALT and AST activities

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

250 - 1000 mg/kg

Kind of Dosing (Pharmacological Data)

250, 500, and 1000 mg/kg, single administration

Method (Pharmacological Data)

180-220 g rats; rats were sacrificed at days 3, 5, 10, and 15 after treatment with title comp.; isolation of blood serum and liver microsomes; biochemical assays

Further Details (Pharmacological Data)

estimation of oxidative damage induced by title comp. by the level of lipid hydroperoxides (LHPs) and 8-hydroxy-2'-deoxyguanosine (8-OH-dG) in liver, and serum activites of alanine aminotransferase (ALT) and aspartate aminotransferase (AST)

Results

title comp. dose-dependently induced AST and ALT activities and the formation of LHP and 8-OH-dG with peaks of LHP and 8-OH-dG at days 3 and 5, resp., and returned to basal levels to day 15

Liu; Chen; Chi; Food and Chemical Toxicology; vol. 37; nb. 7; (1999); p. 697 - 702, View in Reaxys 70 of 102

Effect (Pharmacological Data)

genetic toxicity in vitro

Species or Test-System (Pharmacological Data)

Saccharomyces cerevisiae diploid strain RS112

Concentration (Pharmacological Data)

0.01 - 2 g/l

Kind of Dosing (Pharmacological Data)

title comp.: 0.01, 0.1, 1 and 2 mg/ml; hydroxyurea: 75 mM

Exposure Period (Pharmacological Data)

17 h

Method (Pharmacological Data)

cells arrested on S-phase by adding of hydroxyurea; frequencies of DEL and ICR recombinations in survived cells

Further Details (Pharmacological Data)

exposure to title comp. in SC-leu medium at 30 deg C; culture contained 3E7 cells/ml

Results

dose-dependent increase in DEL and ICR recombination frequencies, 2.7 and 6-fold at 2 mg/ml, resp.

Galli, Alvaro; Schiestl, Robert H.; Mutation Research - Genetic Toxicology and Environmental Mutagenesis; vol. 419; nb. 1-3; (1998); p. 53 - 68, View in Reaxys 71 of 102

Effect (Pharmacological Data)

cytotoxicity

Species or Test-System (Pharmacological Data)

Saccharomyces cerevisiae diploid strain RS112

Concentration (Pharmacological Data)

0.001 - 2 g/l

Kind of Dosing (Pharmacological Data)

title comp.: 0.01, 0.1, 1 and 2 mg/ml; hydroxyurea: 75 mM

Exposure Period (Pharmacological Data)

17 h

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Method (Pharmacological Data)

cells arrested on S-phase by adding of hydroxyurea; exposure to title comp.; cell viability

Further Details (Pharmacological Data)

incubation in in SC-leu medium at 30 deg C; culture contained 3E7 cells/ml

Results

rapid dose-dependent decrease in cell viability to 0.8 and 0.09 percent at 1 and 2 mg/ml, resp.

Galli, Alvaro; Schiestl, Robert H.; Mutation Research - Genetic Toxicology and Environmental Mutagenesis; vol. 419; nb. 1-3; (1998); p. 53 - 68, View in Reaxys 72 of 102

Effect (Pharmacological Data)

mutagenic (microorganism)

Species or Test-System (Pharmacological Data)

Salmonella typhimurium TA102

Concentration (Pharmacological Data)

78 - 1250 μg/plate

Method (Pharmacological Data)

plate incorporation assay; with metabolic activation (S9 mix); plates incubated at 37 deg C for 48 h; number of revertants/plate scored

Further Details (Pharmacological Data)

dissolved in DMSO; title comp. tested in at least two replicate experiments and in two laboratories

Comment (Pharmacological Data)

No effect

Watanabe, Kazuko; Sasaki, Toshiaki; Kawakami, Kumiko; Mutation Research - Genetic Toxicology and Environmental Mutagenesis; vol. 416; nb. 3; (1998); p. 169 - 181, View in Reaxys 73 of 102

Effect (Pharmacological Data)

mutagenic (microorganism)

Species or Test-System (Pharmacological Data)

Salmonella typhimurium TA2638

Concentration (Pharmacological Data)

78 - 2500 μg/plate

Method (Pharmacological Data)

plate incorporation assay; with metabolic activation (S9 mix); plates incubated at 37 deg C for 48 h; number of revertants/plate scored

Further Details (Pharmacological Data)

dissolved in DMSO; title comp. tested in at least two replicate experiments and in two laboratories

Comment (Pharmacological Data)

No effect

Watanabe, Kazuko; Sasaki, Toshiaki; Kawakami, Kumiko; Mutation Research - Genetic Toxicology and Environmental Mutagenesis; vol. 416; nb. 3; (1998); p. 169 - 181, View in Reaxys 74 of 102

Effect (Pharmacological Data)

mutagenic (microorganism)

Species or Test-System (Pharmacological Data)

Escherichia coli WP2/pKM101

Concentration (Pharmacological Data)

78 - 2500 μg/plate

Method (Pharmacological Data)

plate incorporation assay; with metabolic activation (S9 mix); plates incubated at 37 deg C for 48 h; number of revertants/plate scored

Further Details (Pharmacological Data)

dissolved in DMSO; title comp. tested in at least two replicate experiments and in two laboratories

Comment (Pharmacological Data)

No effect

Watanabe, Kazuko; Sasaki, Toshiaki; Kawakami, Kumiko; Mutation Research - Genetic Toxicology and Environmental Mutagenesis; vol. 416; nb. 3; (1998); p. 169 - 181, View in Reaxys 75 of 102

Effect (Pharmacological Data)

mutagenic (microorganism)

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Species or Test-System (Pharmacological Data)

Escherichia coli WP2 uvrA/pKM101

Concentration (Pharmacological Data)

78 - 2500 μg/plate

Method (Pharmacological Data)

plate incorporation assay; with metabolic activation (S9 mix); plates incubated at 37 deg C for 48 h; number of revertants/plate scored

Further Details (Pharmacological Data)

dissolved in DMSO; title comp. tested in at least two replicate experiments and in two laboratories

Comment (Pharmacological Data)

No effect

Watanabe, Kazuko; Sasaki, Toshiaki; Kawakami, Kumiko; Mutation Research - Genetic Toxicology and Environmental Mutagenesis; vol. 416; nb. 3; (1998); p. 169 - 181, View in Reaxys 76 of 102

Effect (Pharmacological Data)

antitumor

Species or Test-System (Pharmacological Data)

Raji cells derived from Burkitt's lymphoma

Exposure Period (Pharmacological Data)

48 h

Method (Pharmacological Data)

in vitro; Epstein-Barr virus early antigen (EBV-EA) activation assay; RPMI-1640 medium; 37 deg C; TPA; indirect immunofluorescence technique

Results

exhibited significant inhibitory effect on EBV-EA activation

Takasaki, Midori; Konoshima, Takao; Yasuda, Ichiro; Hamano, Tomoko; Tokuda, Harukuni; Biological and Pharmaceutical Bulletin; vol. 20; nb. 7; (1997); p. 776 - 780, View in Reaxys 77 of 102

Effect (Pharmacological Data)

genotoxic

Species or Test-System (Pharmacological Data)

Chinese hamster lung cells

Sex

female

Concentration (Pharmacological Data)

0.025 - 0.2 mg/g

Kind of Dosing (Pharmacological Data)

Solution of title comp. in dimethylsulfoxid (DMSO) in final conc. 0.5 percent v/v

Method (Pharmacological Data)

newborn hamster; lung cells culture in Eagle's medium; title comp. administered with or without S9 for 6 h; than incubated for further 21 h with 5-bromo-2'-deoxyuridine in final conc. 0.5 μg/ml; 32P-postlabeling assay for determination of DNA-adducts

Further Details (Pharmacological Data)

S9: rat liver postmitochondrial supernatant fraction

Results

title comp. in the presence of S9 induced the dose-dependent increase of sister chromatid exchanges and chromosomal aberrations which correlated with title comp.-DNA adducts formation; no effects if S9 was absent

Daimon, Hirohiko; Sawada, Shigeki; Asakura, Shoji; Sagami, Fumio; Teratogenesis Carcinogenesis and Mutagenesis; vol. 17; nb. 1; (1997); p. 7 - 18, View in Reaxys 78 of 102

Effect (Pharmacological Data)

genotoxic

Species or Test-System (Pharmacological Data)

Fischer (F344/Du Crj) rat

Sex

male

Route of Application

intragastric

Concentration (Pharmacological Data)

500 - 1000 mg/kg

Kind of Dosing (Pharmacological Data)

in corn oil; single dose 1000 mg/kg or 5 doses of 500 mg/kg once a day

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Method (Pharmacological Data)

24 h after final title comp. administration hepatocytes isolated; incubated in Williams' medium E with epidermal growth factor to test chromosomal aberrations and sister chromatid exchange (SCE)

Results

title comp. induced SCE; repeated doses induced chromosomal aberrations (mainly chromatid breaks and chromatid exchanges); title comp. induced inhibition of mitosis

Daimon, Hirohiko; Sawada, Shigeki; Asakura, Shoji; Sagami, Fumio; Teratogenesis Carcinogenesis and Mutagenesis; vol. 17; nb. 6; (1997); p. 327 - 337, View in Reaxys 79 of 102

Effect (Pharmacological Data)

genotoxic

Species or Test-System (Pharmacological Data)

Fischer (F344/Du Crj) rat

Sex

male

Route of Application

intragastric

Concentration (Pharmacological Data)

500 - 1000 mg/kg

Kind of Dosing (Pharmacological Data)

in corn oil; single dose 1000 mg/kg or 5 doses of 500 mg/kg once a day

Method (Pharmacological Data)

24 h after final title comp. administration hepatocytes isolated; incubated in Williams' medium E with BrdU; replicative DNA synthesis determined by BrdU incorporation; presence of DNA adducts determined with nuclease P1-enhanced 32P-postlabeling assay

Further Details (Pharmacological Data)

BrdU: 5-bromo-2'-deoxyuridine

Results

two major and two minor DNA adducts observed in liver DNA isolated from rats treated with title comp.; title comp. at repeated doses did not induce replicative DNA synthesis due to severe cytotoxic damage

Daimon, Hirohiko; Sawada, Shigeki; Asakura, Shoji; Sagami, Fumio; Teratogenesis Carcinogenesis and Mutagenesis; vol. 17; nb. 6; (1997); p. 327 - 337, View in Reaxys 80 of 102

Effect (Pharmacological Data)

cytotoxicity

Species or Test-System (Pharmacological Data)

CHO-K1 cells

Concentration (Pharmacological Data)

0.4 - 1 mmol/l

Exposure Period (Pharmacological Data)

Method (Pharmacological Data)

in DMSO; with metabolic activation (4.5 percent v/v S9); frequencies of chromosomal aberrations (CA), endoreduplikations (ERD) and differentially staining sister-chromatids (DSC) in 100, 200 and 100 metaphases counted

Further Details (Pharmacological Data)

cells were grown at 37 deg C in Ham's F-12 medium supplemented with 10 percent FCS, 100 units/ml penicillin and 100 μg/ml streptomycin; ca. 6E5 cells/ml; with 0.5 μg/ml of BUdR; also with 1.5-9.0 percent S9 and 0.6 mM safrole

Results

cells with CAs/100 metaphases: 4, 3, 2, 7; ERDs ( percent): 0.5, 0.5, 2.5, 5.0; DSC ( percent): 98, 95, 69, 24 at the conc. of 0.4, 0.6, 0.8, 1.0 mM, resp. (control: 2, 0.5, 98, resp.)

Tayama, Sumiko; Mutation Research - Genetic Toxicology; vol. 368; nb. 3-4; (1996); p. 249 - 260, View in Reaxys 81 of 102

Effect (Pharmacological Data)

sister chromatid exchange; examination of

Species or Test-System (Pharmacological Data)

CHO-K1 cells

Concentration (Pharmacological Data)

0.4 - 1 mmol/l

Exposure Period (Pharmacological Data)

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Method (Pharmacological Data)

in DMSO; with metabolic activation (4.5 percent v/v S9); 25 metaphases per one group counted

Further Details (Pharmacological Data)

Results

mean SCEs/ml: 9.6, 11.0, 12.0 and 13.0 at the conc. of 0.4, 0.6, 0.8, and 1.0 mM, resp. (control: 6.7)

Tayama, Sumiko; Mutation Research - Genetic Toxicology; vol. 368; nb. 3-4; (1996); p. 249 - 260, View in Reaxys 82 of 102

Effect (Pharmacological Data)

cytotoxicity

Species or Test-System (Pharmacological Data)

CHO-K1 cells

Concentration (Pharmacological Data)

0.4 - 0.9 mg/l

Exposure Period (Pharmacological Data)

Method (Pharmacological Data)

in DMSO; without metabolic activation; frequencies of chromosomal aberrations (CA), endoreduplikations (ERD) and differentially staining sister-chromatids (DSC) in 100, 200 and 100 metaphases counted in exp. 1 an 2, resp.

Further Details (Pharmacological Data)

cells were grown at 37 deg C in Ham's F-12 medium supplemented with 10 percent FCS, 100 units/ml penicillin and 100 μg/ml streptomycin; 2 experiments; ca. 6E5 cells/ml; with 0.5 μg/ml of BUdR

Results

cells with CAs/100 metaphases: 3, 3, 2, 5, 2/3, 2, 1, 3, 2; ERDs ( percent): 0, 0, 0.5, 0.5, 2.0/0, 0, 0.5, 0.5, 2.5; DSC ( percent): 96, 94, 91, 82, 60/97, 90, 89, 84, 42 at the conc. of 0.4, 0.5, 0.6, 0.7, 0.8 μg/ml, resp. (exp 1/exp 2) (control: 0, 0, 99, resp.)

Tayama, Sumiko; Mutation Research - Genetic Toxicology; vol. 368; nb. 3-4; (1996); p. 249 - 260, View in Reaxys 83 of 102

Effect (Pharmacological Data)

sister chromatid exchange; examination of

Species or Test-System (Pharmacological Data)

CHO-K1 cells

Concentration (Pharmacological Data)

0.4 - 0.9 mg/l

Exposure Period (Pharmacological Data)

Method (Pharmacological Data)

in DMSO; without metabolic activation; 25 and 50 metaphases per one group counted in exp. 1 an 2, resp.

Further Details (Pharmacological Data)

cells were grown at 37 deg C in Ham's F-12 medium supplemented with 10 percent FCS, 100 units/ml penicillin and 100 μg/ml streptomycin; 2 experiments; ca. 6E5 cells/ml; with 0.5 μg/ml of BUdR

Results

mean SCEs/ml: 5.8, 6.2, 6.0, 6.8, 7.8 (exp. 1) and 5.8, 7.0, 6.8, 6.9, 7.2 (exp. 2) at the conc. of 0.4, 0.5, 0.6, 0.7, 0.8, 0.9 μg/ml, resp. (control: 5.3-5.5)

Tayama, Sumiko; Mutation Research - Genetic Toxicology; vol. 368; nb. 3-4; (1996); p. 249 - 260, View in Reaxys 84 of 102

Effect (Pharmacological Data)

mutagenic

Species or Test-System (Pharmacological Data)

L5178Y tk+/- mouse lymphoma cell

Concentration (Pharmacological Data)

0.5 - 70 mg/l

Method (Pharmacological Data)

mouse lymphoma assay (MLA); RPMI 1640 medium; cloning was performed with 20 percent heat-inactivated horse serum; colonies were counted 12-14 days following plating; twofold rule; without (60 and 70 mg/l) and with (0.50-10.00 mg/l) 2 percent S9

Further Details (Pharmacological Data)

criteria for a positive result: at least a 2-fold increase in mutant frequency (MF) as compared to the MF of the respective solvent control must be observed at 2 or more test conc. (mutant index MI), relative total growth (RTG) should be => 10 percent

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Results

mutagenicity at 10.00 mg/l with S9; various sources of title comp.

Comment (Pharmacological Data)

No effect

Oberly; Hoffman; Garriott; Mutation Research - Genetic Toxicology; vol. 369; nb. 3-4; (1996); p. 221 - 232, View in Reaxys 85 of 102

Effect (Pharmacological Data)

enzyme; induction of

Species or Test-System (Pharmacological Data)

rat liver microsomes

Sex

male

Concentration (Pharmacological Data)

150 mg

Kind of Dosing (Pharmacological Data)

injection once daily for 4 d in trioctanoin (1.3 ml/kg body weight)

Method (Pharmacological Data)

in vitro; microsomes were prepared from F344 rats (300-400 g) were fed semisynthetic AIN 76A diet with title comp.; add. of 1- or 2-naphthylisothiocyanate (0.5 mM); metabolite determined with 2-aminofluorene (2-AF, 0.2 mM) by HPLC

Further Details (Pharmacological Data)

metabolic conversion was determined by production of urea or thiourea with 2-AF vs. time

Results

title comp. induced enzymes responsible for the oxidative metabolism of isothiocyanates

Lee, Mei-Sie; Chemical Research in Toxicology; vol. 9; nb. 7; (1996); p. 1072 - 1078, View in Reaxys 86 of 102

Effect (Pharmacological Data)

antagonist

Species or Test-System (Pharmacological Data)

antisera from rabbits immunized with DMCA-RSA

Concentration (Pharmacological Data)

1 mmol/l

Method (Pharmacological Data)

antisera from rabbits immunized with DMCA-RSA (dilution 1:50 000) were preincubated with title comp. (30 min, RT) and then added to ELISA plates; tested for recognition of DMCA-RSA; absorbance at 492 nm was determined

Further Details (Pharmacological Data)

DMCA-RSA = protein conjugate prepared by coupling 3,4-dimethoxycinnamic acid to rabbit serum albumin

Comment (Pharmacological Data)

No effect

Gardner, Iain; Bergin, Pauline; Stening, Peter; Kenna, J. Gerald; Caldwell, John; Chemical Research in Toxicology; vol. 9; nb. 4; (1996); p. 713 - 721, View in Reaxys 87 of 102

Effect (Pharmacological Data)

antagonist

Species or Test-System (Pharmacological Data)

antisera from rabbits immunized with AME-RSA

Concentration (Pharmacological Data)

1 mmol/l

Method (Pharmacological Data)

antisera from rabbits immunized with AME-RSA (dilution 1:5000) were preincubated with title comp. (30 min, RT) and then added to ELISA plates; tested for recognition of AMERSA; absorbance at 492 nm was determined

Further Details (Pharmacological Data)

AME-RSA = protein conjugate prepared by coupling 1'-acetoxymethyleugenol to rabbit serum albumin

Results

7 percent inhibition of recognition of the AME-RSA conjugates by the antisera

Gardner, Iain; Bergin, Pauline; Stening, Peter; Kenna, J. Gerald; Caldwell, John; Chemical Research in Toxicology; vol. 9; nb. 4; (1996); p. 713 - 721, View in Reaxys 88 of 102

Effect (Pharmacological Data)

antioxidant

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Species or Test-System (Pharmacological Data)

Wistar rat liver mitochondria

Sex

male

Method (Pharmacological Data)

in vitro; effect on ascorbate/Fe2+-induced lipid peroxidation assayed; Tris-HCl buffer, pH 7.4; sucrose; 10 μM FeSO4; 40 μM sodium ascorbate; 37 deg C; incub. for 20 min; lipid peroxidation assessed by measuring oxygen uptake

Further Details (Pharmacological Data)

dl-α-tocopherol with IC50 value of 16 μM used as positive control

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 100 μmol/l

Uchida, Mihoko; Nakajin, Shizuo; Toyoshima, Satoshi; Shinoda, Masato; Biological and Pharmaceutical Bulletin; vol. 19; nb. 4; (1996); p. 623 - 626, View in Reaxys 89 of 102

Effect (Pharmacological Data)

antioxidant

Species or Test-System (Pharmacological Data)

Wistar rat liver microsomes

Sex

male

Method (Pharmacological Data)

in vitro; effect on NADPH-induced lipid peroxidation assayed; 50 mM potassium phosphate buffer, pH 7.4; 10 μM FeSO4; 20 mM NaCl; NADPH-generating system; 37 deg C; incub. for 7.5 min; lipid peroxidation measured by TBA method

Further Details (Pharmacological Data)

TBA: thiobarbituric acid; dl-α-tocopherol with IC50 value of > 1000 μM used as positive control

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 1000 μmol/l

Uchida, Mihoko; Nakajin, Shizuo; Toyoshima, Satoshi; Shinoda, Masato; Biological and Pharmaceutical Bulletin; vol. 19; nb. 4; (1996); p. 623 - 626, View in Reaxys 90 of 102

Effect (Pharmacological Data)

antioxidant

Species or Test-System (Pharmacological Data)

Wistar rat liver microsomes

Sex

male

Method (Pharmacological Data)

in vitro; effect on CCl4-induced lipid peroxidation assayed; 50 mM potassium phosphate buffer, pH 7.4; 3.4 mM CCl4; 20 mM NaCl; 0.6 mM EDTA; NADPH-generating system; 37 deg C; incub. for 7.5 min; lipid peroxidation measured by TBA method

Further Details (Pharmacological Data)

TBA: thiobarbituric acid; dl-α-tocopherol with IC50 value of 22 μM used as positive control

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

130 μmol/l

Uchida, Mihoko; Nakajin, Shizuo; Toyoshima, Satoshi; Shinoda, Masato; Biological and Pharmaceutical Bulletin; vol. 19; nb. 4; (1996); p. 623 - 626, View in Reaxys 91 of 102

Effect (Pharmacological Data)

antioxidant

Species or Test-System (Pharmacological Data)

lecithin liposomes

Method (Pharmacological Data)

in vitro; effect on Fe2+-induced lipid peroxidation assayed; 50 mM potassium phosphate buffer, pH 7.4; 1 mM FeSO4; 25 deg C; incub. for 60 min; lipid peroxidation measured by TBA method

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Further Details (Pharmacological Data)

TBA: thiobarbituric acid; dl-α-tocopherol with IC50 value of 18 μM used as positive control

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

240 μmol/l

Uchida, Mihoko; Nakajin, Shizuo; Toyoshima, Satoshi; Shinoda, Masato; Biological and Pharmaceutical Bulletin; vol. 19; nb. 4; (1996); p. 623 - 626, View in Reaxys 92 of 102

Comment (Pharmacological Data)

genotoxic effects in the Drosofila melanogaster wing spot test at conc. 0.1-1.0 mM

Batiste-Alentorn, M.; Xamena, N.; Creus, A.; Marcos, R.; Experientia; vol. 51; nb. 1; (1995); p. 73 - 76, View in Reaxys 93 of 102

Effect (Pharmacological Data)

nematocidal

Species or Test-System (Pharmacological Data)

Toxocara canis, second-stage larvae

Concentration (Pharmacological Data)

1 mg/ml

Exposure Period (Pharmacological Data)

25 h

Method (Pharmacological Data)

in vitro; relative mobility (RM) assay; cellular viability expressed by dye exclusion index (DE)

Results

dual effect: fast acting paralytic effect (temporary) and slowly emerging killing effect

Sugimoto; Goto; Akao; Kiuchi; Kondo; Tsuda; Biological and Pharmaceutical Bulletin; vol. 18; nb. 4; (1995); p. 605 - 609, View in Reaxys 94 of 102

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

Balb/C mouse

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

600 μmol/kg

Kind of Dosing (Pharmacological Data)

single dose

Exposure Period (Pharmacological Data)

24 h

Method (Pharmacological Data)

in vivo experiment; total DNA isolating; (32)P-postlabeling analysis of adducts of DNA with the title comp.

Further Details (Pharmacological Data)

mice weighing 20-22 g; title comp. injected as suspension in sesame oil; controls were received oil alone; deoxyribonucleotides from the isolated DNA labeling with (32)P-ATP; adduct mapping by multi-dimentional TLC; quantified by dry scintillation count

Results

N2-(trans-isosafrol-3'-yl)deoxyguanosine and its 3'-dephosphorylated deriv., N2-(trans-safrol-1'-yl)deoxyguanosine, N6-(trans-isosafrol-3'-yl)deoxyadenosine were identified as DNA adducts formed in the liver

Qato; Guenthner; Toxicology Letters; vol. 75; nb. 1-3; (1995); p. 201 - 207, View in Reaxys 95 of 102

Effect (Pharmacological Data)

carcinogenic in vivo

Species or Test-System (Pharmacological Data)

F344 rat

Sex

male

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Concentration (Pharmacological Data)

500 - 1000 mg/kg

Method (Pharmacological Data)

9 week old rats; oral or s.c. treatment; maximum tolerated dose (MTD) - half of LD50 and 1/2 MTD; single dose; replicate DNA synthesis (RDS) observed 24, 39, 48 h post-tr; liver perfused, minced; 2x104 cells 4 h at 37 deg C; in vivo-iv vitro RDS test

Further Details (Pharmacological Data)

when maximum RDS incidence was 2.0 percent or more it was considered to indicate positive response; less than 2 percent - negative

Results

positive

Uno; Takasawa; Miyagawa; Inoue; Murata; Yoshikawa; Mutation Research - Genetic Toxicology; vol. 320; nb. 3; (1994); p. 189 - 205, View in Reaxys 96 of 102

Comment (Pharmacological Data)

antiplatelet aggregative activity (rabbit)

Wu, Tian-Shung; Huang, Shiow-Chyn; Lai, Jeng-Shiow; Teng, Che-Ming; Ko, Feng-Nien; Kuoh, ChangSheng; Phytochemistry (Elsevier); vol. 32; nb. 2; (1993); p. 449 - 452, View in Reaxys 97 of 102

Effect (Pharmacological Data)

carcinogenic in vitro

Species or Test-System (Pharmacological Data)

Syrian hamster

Method (Pharmacological Data)

Syrian hamster embryo (SHE) micronucleus test in vitro; in DMSO solution; incubated for 18 h; 2000 cells counted microscopically from each coverslip, number of cells with micronuclei was determined

Further Details (Pharmacological Data)

substance inducing a reproducible and dose dependent increase in micronucleus frequency regarded as positive

Results

also correlation with literature data for carcinogenicity

Comment (Pharmacological Data)

No effect

Fritzenschaf, H.; Kohlpoth, M.; Rusche, B.; Schiffmann, D.; Mutation Research; vol. 319; nb. 1; (1993); p. 47 54, View in Reaxys 98 of 102

Comment (Pharmacological Data)

Tribolium castaneum Herbst.; synergistic effects with natural pyrethrins

Tomar; Saxena; Agricultural and Biological Chemistry; vol. 50; nb. 8; (1986); p. 2115 - 2116, View in Reaxys 99 of 102

Comment (Pharmacological Data)

MIC >200 μg/ml (against Streptococcus mutans)

Hattori; Hada; Watahiki; Ihara; Shu; Kakiuchi; Mizuno; Namba; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 9; (1986); p. 3885 - 3893, View in Reaxys 100 of 102 Comment (Pharmacological Data)

inhibited the N-oxidation of diethylcarbamazine in male rats (intraperitoneally); enhancement in female rats (intraperitoneally)

Joseph; Dixon; Journal of Pharmacy and Pharmacology; vol. 36; nb. 10; (1984); p. 711 - 712, View in Reaxys 101 of 102 Comment (Pharmacological Data)

no antifungal effect in the presence of 7-10percent NaCl against Aspergillus oryzae, niger and ochraceus, Penicillium citrinum, viridicatum and cyclopium, Fusarium graminearum, Aureobasidium pullulans, Paecilomyces lilacinus

Kurita; Koike; Agricultural and Biological Chemistry; vol. 46; nb. 1; (1982); p. 159 - 165, View in Reaxys 102 of 102 Comment (Pharmacological Data)

antifungal effects at 27 deg C and 1.0-2.0 mM on growth of Blastomyces dermatitidis, Histoplasma capsulatum, Trichophyton rubrum (H), Fonsecaea pedrosoi (T), Penicillium frequentans, Penicillium cyclopium, no activity against Aspergillus nidulans

Kurita; Miyaji; Kurane; Takahara; Agricultural and Biological Chemistry; vol. 45; nb. 4; (1981); p. 945 - 952, View in Reaxys Ecotoxicology (17) 1 of 17

Effect (Ecotoxicology)

antimitotic

Species or Test-System (Ecotoxicology)

Lytechinus variegatus

Concentration (Ecotoxicology)

10 - 100 mg/l

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Method (Ecotoxicology)

sea urchin egg assay; title comp. added to eggs 2 min after fertilization, shaken at 26 deg C and fixed with 10 percent formaldehyde on appropriate time points to obtain first, third or blastulae stages; egg development observed; number of normal cells counted

Further Details (Ecotoxi- doxorubicin at 10 and 100 μg/ml as positive control cology) Results

title comp. inhibited cell cleavage in concentration-dependent manner; inhibition was significant since first cleavage for both tested concentrations

Effect (Ecotoxicology)

microbial activity; effect on

Species or Test-System (Ecotoxicology)

indigenous soil microorganisms

Concentration (Ecotoxicology)

10 - 1000 mg/kg

Kind of Dosing (Ecotoxi- title comp. dissolved in acetone cology) Method (Ecotoxicology)

soils spiked with title comp.; incubated for 14 d at 21 deg C; potential nitrification determined by addition solution (NH4)4SO4 with sodium chlorate and shaked for 5 h

Further Details (Ecotoxi- soil from suburban area south of Adelaide, South Australia: campus soil or garden soil cology) (depth of 0-10 cm, clay 12.5-25 percent, silt 10-22.5 percent, sand 52.5-77.5 percent, pH 7.5-8.5, total carbon 3.01-4.98 percent); water and acetone as controls; duplicate experiments Results

in control acetone inhibited potential nitrification; title comp. stimulated potential nitrification over that in the acetone control at all conc. in campus soil and at 50-1000 ppm in garden soil (histograms)

Scott; Janusz; Perkins; Megharaj; Naidu; Kirkbride; Bulletin of Environmental Contamination and Toxicology; vol. 70; nb. 4; (2003); p. 824 - 831, View in Reaxys 3 of 17

Effect (Ecotoxicology)

microbial activity; effect on

Species or Test-System (Ecotoxicology)

dehydrogenase

Concentration (Ecotoxicology)

10 - 1000 mg/kg

Kind of Dosing (Ecotoxi- title comp. dissolved in acetone cology) Method (Ecotoxicology)

soils spiked with title comp.; incubated for 10 d at 21 deg C; dehydrogenase activity measured by incubation at 37 deg C for 24 h with 2,3,5-triphenyltetrazolium chloride for the production of triphenyltetrazolium formazan

Further Details (Ecotoxi- soil from suburban area south of Adelaide, South Australia: campus or garden soils (depth cology) of 0-10 cm, clay 12.5-25 percent, silt 10-22.5 percent, sand 52.5-77.5 percent, pH 7.5-8.5, total carbon 3.01-4.98 percent); water and acetone as controls; duplicate experiments Results

title comp. stimulated dehydrogenase activity in campus and garden soils at all conc. (histograms)

Scott; Janusz; Perkins; Megharaj; Naidu; Kirkbride; Bulletin of Environmental Contamination and Toxicology; vol. 70; nb. 4; (2003); p. 824 - 831, View in Reaxys 4 of 17

Effect (Ecotoxicology)

genotoxicity

Species or Test-System (Ecotoxicology)

Escherichia coli PQ37

Concentration (Ecotoxicology)

0 - 3.20 μg

Method (Ecotoxicology)

SOS chromotest; with or without S9-mix activation, vehicle DMSO, incubated 37 deg C 2.5 h, β-galactosidase and alkaline phosphatase activity determination

Comment (Ecotoxicology)

No effect

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Kevekordes, Sebastian; Mersch-Sundermann, Volker; Burghaus, Christian M.; Spielberger, Jan; Schmeiser, Heinz H.; Arlt, Volker M.; Dunkelberg, Hartmut; Mutation Research - Genetic Toxicology and Environmental Mutagenesis; vol. 445; nb. 1; (1999); p. 81 - 91, View in Reaxys 5 of 17

Effect (Ecotoxicology)

toxicity to invertebrates

Endpoint of Effect (Ecotoxicology)

repellency

Species or Test-System (Ecotoxicology)

Periplaneta americana (L.)

Method (Ecotoxicology)

linear track olfactometer assay; oflactometer consisting of odour source, two traps, pipework, pot with test insects, wirework; insect nymphs' contact with vapours of title comp. for few min.; insects' climb up the wire during the test

Type (Ecotoxicology)

repellent conc. 50

Value of Type (Ecotoxicology)

8.42 mg/cm-2

Ngoh; Choo; Pang; Huang; Kini; Ho; Pesticide Science; vol. 54; nb. 3; (1998); p. 261 - 268, View in Reaxys 6 of 17

Effect (Ecotoxicology)

toxicity to invertebrates

Endpoint of Effect (Ecotoxicology)

mortality

Species or Test-System (Ecotoxicology)

Periplaneta americana (L.)

Sex

female

Exposure Period (Ecotoxicology)

24 h

Method (Ecotoxicology)

insect contact in incubator with vapours of title comp. from filter paper impregnated with title comp. solution (6 various concentrations); incubation for 24 h at 30 deg C and 75 percent RH; recording of insect mortality after 96 h

Type (Ecotoxicology)

lethal conc. 95

Value of Type (Ecotoxicology)

0.400 mg/cm-2

Ngoh; Choo; Pang; Huang; Kini; Ho; Pesticide Science; vol. 54; nb. 3; (1998); p. 261 - 268, View in Reaxys 7 of 17

Effect (Ecotoxicology)

toxicity to invertebrates

Endpoint of Effect (Ecotoxicology)

knockdown of insects

Species or Test-System (Ecotoxicology)

Periplaneta americana (L.)

Sex

female

Exposure Period (Ecotoxicology)

24 h

Method (Ecotoxicology)

Type (Ecotoxicology)

knockdown concentration 95

Value of Type (Ecotoxicology)

0.279 mg/cm-2

Ngoh; Choo; Pang; Huang; Kini; Ho; Pesticide Science; vol. 54; nb. 3; (1998); p. 261 - 268, View in Reaxys 8 of 17

Effect (Ecotoxicology)

toxicity to invertebrates

Endpoint of Effect (Ecotoxicology)

knockdown of insects

Species or Test-System (Ecotoxicology)

Periplaneta americana (L.)

Sex

female

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Exposure Period (Ecotoxicology)

24 h

Method (Ecotoxicology)

Type (Ecotoxicology)

knockdown concentration 50

Value of Type (Ecotoxicology)

0.159 mg/cm-2

Ngoh; Choo; Pang; Huang; Kini; Ho; Pesticide Science; vol. 54; nb. 3; (1998); p. 261 - 268, View in Reaxys 9 of 17

Effect (Ecotoxicology)

toxicity to invertebrates

Endpoint of Effect (Ecotoxicology)

mortality

Species or Test-System (Ecotoxicology)

Periplaneta americana (L.)

Sex

female

Exposure Period (Ecotoxicology)

24 h

Method (Ecotoxicology)

Type (Ecotoxicology)

LC50

Value of Type (Ecotoxicology)

0.202 mg/cm-2

Ngoh; Choo; Pang; Huang; Kini; Ho; Pesticide Science; vol. 54; nb. 3; (1998); p. 261 - 268, View in Reaxys 10 of 17

Effect (Ecotoxicology)

toxicity to invertebrates

Endpoint of Effect (Ecotoxicology)

mortality

Species or Test-System (Ecotoxicology)

Periplaneta americana (L.)

Sex

female

Exposure Period (Ecotoxicology)

24 h

Method (Ecotoxicology)

insect contact with filter paper impregnated with title comp. solution (6 various concentrations); incubation for 24 h at 30 deg C and 75 percent RH; recording of mortality after 96 h

Type (Ecotoxicology)

tethal concentration 95

Value of Type (Ecotoxicology)

0.464 mg/cm-2

Ngoh; Choo; Pang; Huang; Kini; Ho; Pesticide Science; vol. 54; nb. 3; (1998); p. 261 - 268, View in Reaxys 11 of 17

Effect (Ecotoxicology)

toxicity to invertebrates

Endpoint of Effect (Ecotoxicology)

mortality

Species or Test-System (Ecotoxicology)

Periplaneta americana (L.)

Sex

female

Exposure Period (Ecotoxicology)

24 h

Method (Ecotoxicology)

insect contact with filter paper impregnated with title comp. solution (6 various concentrations); incubation for 24 h at 30 deg C and 75 percent RH; recording of mortality after 96 h

Type (Ecotoxicology)

LC50

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Value of Type (Ecotoxicology)

0.335 mg/cm-2

Ngoh; Choo; Pang; Huang; Kini; Ho; Pesticide Science; vol. 54; nb. 3; (1998); p. 261 - 268, View in Reaxys 12 of 17

Effect (Ecotoxicology)

toxicity to invertebrates

Endpoint of Effect (Ecotoxicology)

knockdown of insects

Species or Test-System (Ecotoxicology)

Periplaneta americana (L.)

Sex

female

Exposure Period (Ecotoxicology)

24 h

Method (Ecotoxicology)

insect contact with filter paper impregnated with title comp. solution (6 various concentrations); incubation for 24 h at 30 deg C and 75 percent RH; knockdown recording

Type (Ecotoxicology)

knockdown concentration for 95 percent of insects

Value of Type (Ecotoxicology)

0.478 mg/cm-2

Ngoh; Choo; Pang; Huang; Kini; Ho; Pesticide Science; vol. 54; nb. 3; (1998); p. 261 - 268, View in Reaxys 13 of 17

Effect (Ecotoxicology)

toxicity to invertebrates

Endpoint of Effect (Ecotoxicology)

knockdown of insects

Species or Test-System (Ecotoxicology)

Periplaneta americana (L.)

Sex

female

Exposure Period (Ecotoxicology)

24 h

Method (Ecotoxicology)

insect contact with filter paper impregnated with title comp. solution (6 various concentrations); incubation for 24 h at 30 deg C and 75 percent RH; knockdown recording

Type (Ecotoxicology)

knockdown concentration for 50 percent of insects

Value of Type (Ecotoxicology)

0.281 mg/cm-2

Ngoh; Choo; Pang; Huang; Kini; Ho; Pesticide Science; vol. 54; nb. 3; (1998); p. 261 - 268, View in Reaxys 14 of 17

Effect (Ecotoxicology)

cytotoxicity

Species or Test-System (Ecotoxicology)

Saccharomyces cerevisiae strain RS112, yeast

Concentration (Ecotoxicology)

0.01 - 4 g/l

Exposure Period (Ecotoxicology)

17 h

Method (Ecotoxicology)

in 4 percent DMSO; G1-arrested yeast cells; colonies counted after 2-3 days; intrachromosomal and interchromosomal recombination (DEL, ICR); numbers of recombinants/1E4 and 1E5 survivors for DEL recombination events and ICR events calculated, resp.

Further Details (Ecotoxi- 3E7 cells/ml exposed in SC-ura-leu medium at 30 deg C; Salmonella-negative carcinocology) gen; 3 independent experiments Results

showed threshold for recombination induction and induced both DEL recombination and ICR at 1 mg/ml (1.5 percent survival); increased 31- and 48-fold DEL recombination and ICR at 4 mg/ml, resp.; dose response of DEL recombination frequencies diagram

Galli, Alvaro; Schiestl, Robert H.; Mutation Research - Genetic Toxicology; vol. 370; nb. 3-4; (1996); p. 209 - 221, View in Reaxys 15 of 17

Effect (Ecotoxicology)

carcinogenic

Species or Test-System (Ecotoxicology)

Saccharomyces cerevisiae, yeast

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Concentration (Ecotoxicology)

100 - 1600 mg/l

Exposure Period (Ecotoxicology)

17 h

Method (Ecotoxicology)

diploid strain RS112; frequency of deletion (DEL) and interchromosomal recombination (ICR); with and without metabolic activ.; S9 from Aroclor-1254-induced rat liver; 30 deg C; colonies counted after 2-3 d of inc.; International Program on Chem. Safety

Results

increase in DEL recombination frequency 5-fold, ECR more than 40-fold; these effect completely abolished in the presence of S9

Carls; Schiestl; Mutation Research - Genetic Toxicology; vol. 320; nb. 4; (1994); p. 293 - 303, View in Reaxys 16 of 17

Effect (Ecotoxicology)

mortality

Species or Test-System (Ecotoxicology)

Drosophila melanogaster (wi)4

Sex

male and female

Route of Application

peroral

Concentration (Ecotoxicology)

0.5 - 1 mmol/l

Method (Ecotoxicology)

pre-imaginal mortality; solvent: 5 percent EtOH plus 1 percent Tween 80; no. of larvae treatment: 1000; 72 hr after egg laying, larvae were fed with title compound during the rest of their development until pupation

Results

no. adults emerged: females 81, 6 (254), males 11, 1 (262); sex-ratio: 7.36, 6.00 (0.97); mortality: 90.80 percent, 99.30 percent (48.40 percent) (conc. 0.50 mM, 1.00 mM, resp.; control in parentheses)

Batiste-Alentorn; Xamena; Creus; Marcos; Environmental and Molecular Mutagenesis; vol. 24; nb. 2; (1994); p. 143 - 147, View in Reaxys 17 of 17

Effect (Ecotoxicology)

mutation

Endpoint of Effect (Ecotoxicology)

eye color mosaicism

Species or Test-System (Ecotoxicology)

Drosophila melanogaster (wi)4

Route of Application

peroral

Concentration (Ecotoxicology)

0.5 - 1 mmol/l

Method (Ecotoxicology)

solvent: 5 percent EtOH plus 1 percent of Tween 80; eye color mosaicism detected in adult males; 72 hr after egg laying, larvae were fed with title compound during the rest of their development until pupation

Results

eyes scored: 972, 1180, 1342; spots: 4 (0.41 percent), 10 (0.85 percent), 4 (0.30 percent); males with eye color mosaicism: 4, 10, 4 (conc. 0.50 mM, 1.00 mM, control, resp.)

Batiste-Alentorn; Xamena; Creus; Marcos; Environmental and Molecular Mutagenesis; vol. 24; nb. 2; (1994); p. 143 - 147, View in Reaxys Concentration in the Environment (1) 1 of 1

Media (Concentration in the Environment)

semicoking tar of lignites

Location

Klimovsk open pit, near-Moscow fields

Method, Remarks (Concentration in the Environment)

eluate 3; preparative TLC on Silufol (eluate Me2CO:toluene:CHCl3 1:6:13); elemental, functional, emission spectrum, structural-group analyses; IR, UV, 1H and 13C NMR spectroscopy, chromatography-MS, cryoscopy

Platonov; Proskuryakov; Antonio, Teka Zheremiash; Ryl'tsova; Platonova; Shvykin; Russian Journal of Applied Chemistry; vol. 72; nb. 2; (1999); p. 316 - 326, View in Reaxys Use (17) Use Pattern

Location

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controlling the population size of Papilio demoleus in combination with attractant

Page/Page colPatent; UNIVERSITY OF THE WEST INDIES, A REGIONAL INSTITUTION, ESTABumn 31-33; 35-36 LISHED BY ROYAL CHARTER; YEE, Trevor, Herbert; WATSON, Charah, Tabetha; GARRAWAY, Eric; ROBINSON, Dwight; GARCIA, Nemoi Nastassia, Sri; WO2011/92600; (2011); (A2) English, View in Reaxys

pest control agent Page/Page colPatent; UNIVERSITY OF THE WEST INDIES, A REGIONAL INSTITUTION, ESTABfor reducing the umn 31-33; 35-36 LISHED BY ROYAL CHARTER; YEE, Trevor, Herbert; WATSON, Charah, Tabetha; number of citrusGARRAWAY, Eric; ROBINSON, Dwight; GARCIA, Nemoi Nastassia, Sri; feeding butterflies WO2011/92600; (2011); (A2) English, View in Reaxys reducing the num- Page/Page colPatent; UNIVERSITY OF THE WEST INDIES, A REGIONAL INSTITUTION, ESTABber butterflies in umn 31-33; 35-36 LISHED BY ROYAL CHARTER; YEE, Trevor, Herbert; WATSON, Charah, Tabetha; combination with GARRAWAY, Eric; ROBINSON, Dwight; GARCIA, Nemoi Nastassia, Sri; attractant WO2011/92600; (2011); (A2) English, View in Reaxys increases endothelial nitric oxide synthase (eNOS) activity

Patent; Melbrosin International Produktions- und Vertriebs GesmbH and Co KG; US2008/131534; (2008); (A1) English, View in Reaxys

metabolic syndrome

Patent; Melbrosin International Produktions- und Vertriebs GesmbH and Co KG; US2008/131534; (2008); (A1) English, View in Reaxys

osteoporosis

Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; WO2008/96998; (2008); (A1) English, View in Reaxys

health care food for preventing osteoporosis

Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; WO2008/96998; (2008); (A1) English, View in Reaxys

Beverages

Page/Page column 1

Patent; FLEXITRAL, INC; WO2008/9926; (2008); (A2) English, View in Reaxys

Topical antiseptic

Page/Page column 1

Patent; FLEXITRAL, INC; WO2008/9926; (2008); (A2) English, View in Reaxys

Pediculicide

Page/Page column 1

Patent; FLEXITRAL, INC; WO2008/9926; (2008); (A2) English, View in Reaxys

Fragrance

Page/Page column 2

Patent; FLEXITRAL, INC; WO2008/9926; (2008); (A2) English, View in Reaxys

Floor waxe

Page/Page column 2

Patent; FLEXITRAL, INC; WO2008/9926; (2008); (A2) English, View in Reaxys

Polishe

Page/Page column 2

Patent; FLEXITRAL, INC; WO2008/9926; (2008); (A2) English, View in Reaxys

Ecstasy manufac- Page/Page colture umn 2

Patent; FLEXITRAL, INC; WO2008/9926; (2008); (A2) English, View in Reaxys

CYP3A4 inhibitor

Patent; LIFECYCLE PHARMA A/S; WO2006/136175; (2006); (A2) English, View in Reaxys

pharmaceutical composition with enhanced oral bioavailability of tacrolimus

Patent; LIFECYCLE PHARMA A/S; WO2006/136175; (2006); (A2) English, View in Reaxys

irritates the nasal passages and/or pharynx

Patent; Bartholomaus, Johannes; Kugelmann, Heinrich; US2005/31546; (2005); (A1) English, View in Reaxys

Isolation from Natural Product (54) Isolation from Comment (IsolaNatural Product tion from Natural Product) dried seed kernels of Myristica fragrans Houtt; purchased from Anguo Chinese Medicinal Herbs Market (Anguo

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071200, Baoding, Hebei Province, P. R. China). dried seeds of extraction, metha- Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; Myristica fragrans nol; extraction, WO2008/96998; (2008); (A1) English, View in Reaxys water/ethyl acetate (1:1); chromatography of ethyl acetate fraction, silica gel, nhexane/ethyl acetate (10:1 to 0.1); chromatography, silica gel, n-hexane/ethyl acetate (100:1); reverse phase chromatography, RP-18, 80 percent methanol stems of Piper sanctum (Miq.) Schl. (Piperaceae), collected in San Andres Tuxtla, State of Veracruz, Mexico

Ocotea pretiosa

De Araujo Jr., Joao X.; Barreiro, Eliezer J.; Parente, Jose P.; Fraga, Carlos A. M.; Synthetic Communications; vol. 29; nb. 2; (1999); p. 263 - 273, View in Reaxys

leaves of Piper aduncum

Parmar, Virinder S.; Jain, Subhash C.; Gupta, Sangita; Talwar, Sangeeta; Rajwanshi, Vivek K.; Kumar, Rajesh; Azim, Abul; Malhotra, Sanjay; Kumar, Naresh; Jain, Rajni; Sharma, Nawal K.; Tyagi, Om D.; Lawrie, Stephen J.; Errington, William; Howarth, Oliwer W.; Olsen, Carl E.; Singh, Sanjay K.; Wengel, Jesper; Phytochemistry; vol. 49; nb. 4; (1998); p. 1069 - 1078, View in Reaxys

Illicium dunnianum by extraction with CH2Cl2 in Soxhlet apparatus for 8 h, removal of solvent and chromatograophy

Sy, Lai-King; Saunders, Richard M. K.; Brown, Geoffrey D.; Phytochemistry; vol. 44; nb. 6; (1997); p. 1099 - 1108, View in Reaxys

Piper aduncum

Parmar, Virinder S.; Jain, Subhash C.; Bisht, Kirpal S.; Jain, Rajni; Taneja, Poonam; Jha, Amitabh; Tyagi, Om D.; Prasad, Ashok K.; Wengel, Jesper; Olsen, Carl E.; Boll, Per M.; Phytochemistry; vol. 46; nb. 4; (1997); p. 597 - 673, View in Reaxys

radix of Asiasarum heterotropoides var. mandshuricum (China)

Takasaki, Midori; Konoshima, Takao; Yasuda, Ichiro; Hamano, Tomoko; Tokuda, Harukuni; Biological and Pharmaceutical Bulletin; vol. 20; nb. 7; (1997); p. 776 - 780, View in Reaxys

Clausena excavata

Wu, Tian-Shung; Huang, Shiow-Chyn; Lai, Jeng-Shiow; Teng, Che-Ming; Ko, FengNien; Kuoh, Chang-Sheng; Phytochemistry (Elsevier); vol. 32; nb. 2; (1993); p. 449 452, View in Reaxys

Piper auritum

Nair, Muraleedharan G.; Sommerville, John; Burke, Basil A.; Phytochemistry (Elsevier); vol. 28; nb. 2; (1989); p. 654 - 655, View in Reaxys

lhe petrol extract of the leaves of Drimys winteri

Sierra, Jorge R.; Lopez, Jose T.; Cortes, Manuel J.; Phytochemistry (Elsevier); vol. 25; nb. 1; (1986); p. 253 - 254, View in Reaxys

leaves of Illicum tashiroi MAXIM., collected on Iriomote Island (Japan)

Yakushijin, Kenichi; Tohshima, Tomoko; Suzuki, Rika; Murata, Hiroyuki; Lu, ShengTen; Furukawa, Hiroshi; Chemical & Pharmaceutical Bulletin; vol. 31; nb. 8; (1983); p. 2879 - 2883, View in Reaxys

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aus Pogostemon plectranthoides (Desf.)

Nigam; Ramaiah; Riechstoffe und Aromen; vol. 22; (1972); p. 378,388, View in Reaxys

aus Anethum graveolens

Baslas; Baslas; Riechstoffe und Aromen; vol. 22; (1972); p. 155,156,158, View in Reaxys

aus aether. Oel v. Saccopetalum tomentosum

Ramaiah; Nigam; Riechstoffe und Aromen; vol. 22; (1972); p. 71,74, View in Reaxys

aus Eugenia bracteata Roxb.

Narasimha; Nigam; Riechstoffe und Aromen; vol. 22; (1972); p. 231,236, View in Reaxys

aus Anethum sowa KURZ

Baslas; Baslas; Riechstoffe und Aromen; vol. 22; (1972); p. 200,202, View in Reaxys

aus Magnolia salicifolia

Fujita; Fujita; Chemical and Pharmaceutical Bulletin; vol. 20; (1972); p. 2251, View in Reaxys

aus Acorus gramineus

Fujita et al.; Yakugaku Zasshi; vol. 90; (1970); p. 1367,1371; Chem.Abstr.; vol. 74; nb. 34553; (1971), View in Reaxys

Bananenaromastoff, Gaschromat. Nachweis

Tressl,R. et al.; Z. Naturforsch., B: Anorg. Chem., Org. Chem., Biochem., Biophys.,; vol. 24; (1969); p. 781 - 783, View in Reaxys

aus d. Blaettern v. Hamamelis virginiana L.

Messerschmidt; Arzneimittel-Forschung; vol. 18; nb. 12; (1968); p. 1618 - 1618, View in Reaxys

aether. Oel aus Ocimum basilicum

Hoerhammer et al.; Journal of Pharmaceutical Sciences; vol. 53; (1964); p. 1033; Chem.Abstr.; nb. 305; (1962), View in Reaxys

........... Oil aus Myristica fraga.s

Bejnarowicz; Kirch; Journal of Pharmaceutical Sciences; vol. 52; (1963); p. 988, View in Reaxys

aetherisches Oel von Eremopleila Longifolia F.Muell.

Della; Jefferies; Australian Journal of Chemistry; vol. 14; (1961); p. 663, View in Reaxys

Petersiliensamenoel

Dallacker et al.; Monatshefte fuer Chemie; vol. 91; (1960); p. 1089,1096, View in Reaxys

Schinus weinmanniae folius

Fester et al.; Revista de la Facultad de Ingenieria Quimica (Universidad Nacional del Litoral); vol. 28; (1959); p. 9; Chem.Abstr.; vol. 55; nb. 10809; (1961), View in Reaxys

aus dem aetherischen Oel des Holzes von Ocotea pretiosa

Hickey; Journal of Organic Chemistry; vol. 13; (1948); p. 443,445, View in Reaxys; Raoul; Jachan; Rev. Quim. ind.; vol. 19; (1950); p. 12,13, View in Reaxys

aus dem aetherischen Oel des Holzes von Sassafras albidum

Hickey; Journal of Organic Chemistry; vol. 13; (1948); p. 443,445, View in Reaxys

aus dem aetherischen Oel der Blaetter von Cinnamomum micranthum

Fujita; Tamashita; Nippon Kagaku Kaishi; vol. 65; (1944); p. 385,388, 591; Chem.Abstr.; (1947); p. 3509, View in Reaxys

aus dem aetherischen Oel der Blaetter von Cinnamomum camphora

Fujita; Nippon Kagaku Kaishi; vol. 63; (1942); p. 58,62; Chem.Abstr.; (1947); p. 3509, View in Reaxys; Naito; Nippon Kagaku Kaishi; vol. 64; (1943); p. 1125; Chem.Abstr.; (1947); p. 3776, View in Reaxys

aus dem aetherischen Oel der Blaetter von Illicium parviflorum

Foote; Journal of the American Pharmaceutical Association (1912-1977); vol. 27; (1938); p. 573, View in Reaxys

aus dem aetherischen Oel der

Chabeau; Bl. Acad. Med. Belgique; vol. <6> 3; (1938); p. 46,52, View in Reaxys

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Rinde von Nemuaron humboldtii aus dem aetherischen Oel der Wurzeln von Ligusticum acutilobum

Noguchi et al.; Yakugaku Zasshi; vol. 57; (1937); p. 769,773; dtsch. Ref. S. 187; Chem.Abstr.; (1938); p. 3360, View in Reaxys; Noguchi; Kawanami; Yakugaku Zasshi; vol. 57; (1937); p. 783,788; dtsch. Ref. S. 196, 199; Chem. Zentralbl.; vol. 108; nb. II; (1937); p. 4050, View in Reaxys

aus dem aetherischen Oel der Wurzeln von Asarum sieboldii

Kaku; Kondo; Yakugaku Zasshi; vol. 51; (1931); p. 8,16; dtsch. Ref. S. 3, 6; Chem.Abstr.; (1931); p. 1948, View in Reaxys

bildet den Hauptbestandteil der aether. Oele aus der Rinde und den Blaettern von Laurelia serrata Bert.

Fester; Salgado; Angewandte Chemie; vol. 42; (1929); p. 988, View in Reaxys; Schimmel and Co.; Ber. Schimmel 1927, 61; C. 1927 II, 1518, View in Reaxys

aus dem aetherischen Oel der Blaetter von Boronia pinnata

Penfold; Journal and Proceedings of the Royal Society of New South Wales; vol. 62; (1928); p. 225,230, View in Reaxys

im aether. Oel aus den Blaettern von Doryphora Sassafras

Penfold; Perfumery and Essential Oil Record; vol. 13; p. 273; Chem. Zentralbl.; vol. 93; nb. IV; (1922); p. 673, View in Reaxys

im Pichurimbohnen-Oel

Roure-Bertrand fils; Chem. Zentralbl.; vol. 93; nb. I; (1922); p. 360, View in Reaxys

Vorkommen in verschiedenen japanischen aetherischen Oelen

Anonymus; Chem. Zentralbl.; vol. 91; nb. III; (1920); p. 597, View in Reaxys

Im aether. Oel der Rinde von Cinnamomum Oliveri Bail.

Hargreaves; Journal of the Chemical Society; vol. 109; (1916); p. 751, View in Reaxys

Im aether. Oel der Blaetter von Atherosperma moschatum Labill.

Scott; Journal of the Chemical Society; vol. 101; (1912); p. 1613, View in Reaxys

Im aether. Oel des Holzes von Cinnamomum glanduliferum Meissn.

Pickles; Journal of the Chemical Society; vol. 101; (1912); p. 1437, View in Reaxys

Safrol ist der Hauptbestandteil des Oeles aus dem Holz von Cinnamomum Parthenoxylon Meissn.

Schimmel and Co.; Chem. Zentralbl.; vol. 82; nb. I; (1911); p. 1837, View in Reaxys

Vorkommen im Oel der Fruechte von Illicium verum (Sternanisoel)

Schimmel and Co.; Chem. Zentralbl.; vol. 81; nb. I; (1910); p. 1719, View in Reaxys

im aether. Oel aus der Wurzelrinde von Cinnamomum ceylanicum

Pilgrim; Chem. Zentralbl.; vol. 80; nb. I; (1909); p. 534, View in Reaxys

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im aether. Muskatnussoel (Ol. Nucis moschatae)

Power; Salway; Journal of the Chemical Society; vol. 91; (1907); p. 2045,2049, View in Reaxys

im californischen Lorbeerblaetteroel (von Umbellularia californica)

Power; Lees; Journal of the Chemical Society; vol. 85; (1904); p. 638, View in Reaxys

im aether. Rindenoel von Cinnamomum pedatinervium

Goulding; Journal of the Chemical Society; vol. 83; (1903); p. 1099, View in Reaxys

als Hauptbestandteil des aether. Oels der Wurzel und des Wurzelstocks von Asarum arifolium

Miller; Archiv der Pharmazie (Weinheim, Germany); vol. 240; (1902); p. 377, View in Reaxys

im Oel aus den Blaettern und den gruenen Fruechten von Illicium religiosum (Japanisches Sternanisoel)

Eijkman; Recueil des Travaux Chimiques des Pays-Bas; vol. 4; (1885); p. 39, View in Reaxys; Tardy; Bulletin de la Societe Chimique de France; vol. <3> 27; (1902); p. 995, View in Reaxys

im Wurzelholz und in der Wurzelrinde von Sassafras officinalis Nees (Sassafraswurzeloel)

Grimaux; Ruotte; Bulletin de la Societe Chimique de France; vol. <2> 11; (1869); p. 465; Justus Liebigs Annalen der Chemie; vol. 152; (1869); p. 91, View in Reaxys; Flueckiger; Annalen der Physik (Weinheim, Germany); vol. 158; (1876); p. 248, View in Reaxys; Power; Kleber; Chem. Zentralbl.; vol. 68; nb. II; (1897); p. 42, View in Reaxys; Saint-Evre; Annales de Chimie (Cachan, France); vol. <3> 12; (1844); p. 107; Justus Liebigs Annalen der Chemie; vol. 52; (1844); p. 397, View in Reaxys; Binder; Buchners Repertorium fuer die Pharmacie 11 <1821>, 346, View in Reaxys

im Massoirindenoel (Cinnamomum, Spezies unsicher)

Woy; Archiv der Pharmazie (Weinheim, Germany); vol. 228; (1890); p. 40, View in Reaxys

im Campheroel (Cinnamomum Camphora)

Schimmel and Co.; Bericht vom September 1885, 7, View in Reaxys

Vorkommen von Safrol in weiteren aetherischen Oelen

Semmler; Die aetherischen Oele, Bd. IV <Leipzig 1907>, S. 144ff, View in Reaxys

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