5-(prop-1-en-1-yl)benzo[d][1,3]dioxole [Isosafrole] by Asch

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Date

6 substances in Reaxys

2016-07-07 21h:40m:04s (EST)

1. Query O

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

(1. Query) AND NOT itemno in (6,5,4)

3 substances in Reaxys

2016-07-07 21h:41m:37s (EST)

3. Query

(2. Query) AND itemno in (1)

1 substances in Reaxys

2016-07-07 22h:05m:25s (EST)

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Reaxys ID 82640 View in Reaxys

1/1 CAS Registry Number: 120-58-1 Chemical Name: isosafrole; (E/Z)-3,4-(methylenedioxy)-βmethylstyrene; 5-prop-1-enylbenzo[1,3]dioxole; Isosafrole; isosaffrol; isosafrol; 5-propenyl-benzo[1,3]dioxole Linear Structure Formula: C10H10O2 Molecular Formula: C10H10O2 Molecular Weight: 162.188 Type of Substance: heterocyclic InChI Key: VHVOLFRBFDOUSH-UHFFFAOYSA-N Note:

O O

Substance Label (12) Label References ISO

Rey-Grobellet; Eeckhoutte; Sutra; Alvinerie; Galtier; Xenobiotica; vol. 26; nb. 7; (1996); p. 765 - 778, View in Reaxys; Sada, Nagisa; Lee, Suni; Katsu, Takashi; Otsuki, Takemi; Inoue, Tsuyoshi; Science; vol. 347; nb. 6228; (2015); p. 1362 - 1367, 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

Sharma, Rohit; Abbat, Sheenu; Mudududdla, Ramesh; Vishwakarma, Ram A.; Bharatam, Prasad V.; Bharate, Sandip B.; Tetrahedron Letters; vol. 56; nb. 27; (2015); p. 4057 - 4059; Art.No: 46211, View in Reaxys

Tomita, Ren; Yasu, Yusuke; Koike, Takashi; Akita, Munetaka; Angewandte Chemie - International Edition; vol. 53; nb. 28; (2014); p. 7144 - 7148; Angew. Chem.; vol. 126; nb. 28; (2014); p. 7272 - 7276,5, View in Reaxys

Rajagopalan, Aashrita; Schober, Markus; Emmerstorfer, Anita; Hammerer, Lucas; Migglautsch, Anna; Seisser, Birgit; Glueck, Silvia. M.; Niehaus, Frank; Eck, Juergen; Pichler, Harald; Gruber, Karl; Kroutil, Wolfgang; ChemBioChem; vol. 14; nb. 18; (2013); p. 2427 - 2430, View in Reaxys

Lummiss, Justin A. M.; Oliveira, Kelley C.; Pranckevicius, Alexandre M. T.; Santos, Alexandra G.; Dos Santos, Eduardo N.; Fogg, Deryn E.; Journal of the American Chemical Society; vol. 134; nb. 46; (2012); p. 18889 - 18891, View in Reaxys

Alvarez, Heiddy Marquez; Barbosa, Dayse P.; Fricks, Alini Tinoco; Aranda, Donato A. G.; Valdes, Ricardo H.; Antunes; Organic Process Research and Development; vol. 10; nb. 5; (2006); p. 941 - 943, View in Reaxys

Crudden; Allen; Mikoluk; Sun; Chemical Communications; nb. 13; (2001); p. 1154 - 1155, 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

Tsukada; Sato; Inoue; Chemical Communications; nb. 3; (2001); p. 237 - 238, View in Reaxys

Akai; Morita; Iio; Nakamura; Kita; Organic letters; vol. 2; nb. 15; (2000); p. 2279 - 2282, View in Reaxys

CXVIII

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

ISF

Padma, Palghat Raghunathan; Oesch-Bartlomowicz, Barbara; Hengstler, Jan Georg; Oesch, Franz; Archives of Toxicology; vol. 71; nb. 10; (1997); p. 655 - 659, View in Reaxys

Patent-Specific Data (1) References Patent; BioDiem, Ltd; Denisenko, Peter Prokofievich; Sapronov, Nikolay Sergeevich; Tarasenko, Alexander Alexandrovich; US2015/258059; (2015); (A1) English, View in Reaxys Related Structure (1) Related Structure References Isosafrol-Praeparate, die durch Isomerisierung von Safrol erhalten worden sind, bestehen ueberwiegend aus #trans!-Isosafrol..

Naves; Ardizio; Bulletin de la Societe Chimique de France; (1957); p. 1053,1056, View in Reaxys; Shulgin; J. Chromatographie; vol. 30; (1967); p. 54,60, View in Reaxys

Derivative (1)

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Comment (Derivative)

References

Isosafrolpolyperoxid <C10H10O4>(n): aus Isosafrol, O2 in Eg. (neben and. Verb.); F: 114grad; IR-Banden

Baranova et al.; J. Appl. Chem. USSR (Engl. Transl.); vol. 47; (1974); p. 2751,2840,2841, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

6.7 - 6.8

Waterman; Priester; Chemische Berichte; vol. 48; (1929); p. 1272, View in Reaxys Boiling Point (14) Boiling Point [°C] Pressure (Boiling Point) [Torr]

References

111 - 112

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

131

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

112 - 116

Cabiddu et al.; Annali di Chimica (Rome, Italy); vol. 52; (1962); p. 1261,1263, View in Reaxys

120

Haase; Acta Poloniae Pharmaceutica; vol. 17; (1960); p. 241,242; Chem.Abstr.; vol. 55; nb. 14351; (1961), View in Reaxys

252

760

Lecat; Ann. Soc. scient. Bruxelles; vol. 48; (1928); p. 122, View in Reaxys

127 - 128

Krassusky; Kussner; Journal fuer Praktische Chemie (Leipzig); vol. <2> 115; (1927); p. 332, View in Reaxys

125 - 127

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

252.4 - 252.7

768

Hoering; Baum; Chemische Berichte; vol. 42; (1909); p. 3080, View in Reaxys

123

11.5

Hoering; Baum; Chemische Berichte; vol. 42; (1909); p. 3080, View in Reaxys

116 - 117

Hoering; Baum; Chemische Berichte; vol. 42; (1909); p. 3080, View in Reaxys

253.5

735.4

v. Rechenberg,C.; Einfache und fraktionierte Destillation, 2. Aufl. <Miltitz 1923>, S. 300, View in Reaxys

179.5

100

v. Rechenberg,C.; Einfache und fraktionierte Destillation, 2. Aufl. <Miltitz 1923>, S. 300, View in Reaxys

135.6

v. Rechenberg,C.; Einfache und fraktionierte Destillation, 2. Aufl. <Miltitz 1923>, S. 300, View in Reaxys

120.2

v. Rechenberg,C.; Einfache und fraktionierte Destillation, 2. Aufl. <Miltitz 1923>, S. 300, View in Reaxys

Refractive Index (16) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.5785

589

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

1.5784

589

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

1.5772

589

Cabiddu et al.; Annali di Chimica (Rome, Italy); vol. 52; (1962); p. 1261,1263, View in Reaxys

1.5782

589

Waterman; Priester; Recueil des Travaux Chimiques des Pays-Bas; vol. 47; (1928); p. 849 Anm. 3; 1033, View in Reaxys; Haase; Acta Poloniae Pharmaceutica; vol. 17; (1960); p. 241,242; Chem.Abstr.; vol. 55; nb. 14351; (1961), View in Reaxys

1.5777

589

Boeeseken; Elsen; Recueil des Travaux Chimiques des Pays-Bas; vol. 48; (1929); p. 367, View in Reaxys

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1.5708

656.3

Waterman; Priester; Recueil des Travaux Chimiques des Pays-Bas; vol. 47; (1928); p. 849 Anm. 3; 1033, View in Reaxys

1.5986

486.1

Waterman; Priester; Recueil des Travaux Chimiques des Pays-Bas; vol. 47; (1928); p. 849 Anm. 3; 1033, View in Reaxys

1.6183

434

Waterman; Priester; Recueil des Travaux Chimiques des Pays-Bas; vol. 47; (1928); p. 849 Anm. 3; 1033, View in Reaxys

1.5686

656.3

19.3

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

1.5759

589

19.3

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

1.5957

486.1

19.3

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

1.5746

589

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

1.5786

589

Hoering; Baum; Chemische Berichte; vol. 42; (1909); p. 3080, View in Reaxys

1.5693

656.3

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

1.5763

589

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

1.6155

434

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

Density (4) 1 of 4

Density [g·cm-3]

1.122

Reference Temperature [°C]

Measurement Temperature [°C]

Waterman; Priester; Recueil des Travaux Chimiques des Pays-Bas; vol. 47; (1928); p. 849 Anm. 3; 1033, View in Reaxys 2 of 4

Density [g·cm-3]

1.116

Reference Temperature [°C]

Measurement Temperature [°C]

Dunstan; Hilditch; Zeitschrift fuer Elektrochemie und Angewandte Physikalische Chemie; vol. 18; (1912); p. 187,884, View in Reaxys 3 of 4

Density [g·cm-3]

1.1227

Reference Temperature [°C]

17.5

Measurement Temperature [°C]

Hoering; Baum; Chemische Berichte; vol. 42; (1909); p. 3080, View in Reaxys 4 of 4

Density [g·cm-3]

1.128

Measurement Temperature [°C]

Eijkman; Chemische Berichte; vol. 23; (1890); p. 862, View in Reaxys Azeotropes (MCS) (11) 1 of 11

Temperature (Azeotropes (MCS)) [°C]

99.8

Pressure (Azeotropes (MCS)) [Torr]

760

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Azeotropes

water

Temperature (Azeotropes (MCS)) [°C]

192.8

Pressure (Azeotropes (MCS)) [Torr]

760

Azeotropes

glycol

Temperature (Azeotropes (MCS)) [°C]

243.9

Pressure (Azeotropes (MCS)) [Torr]

760

Azeotropes

glycerol

Temperature (Azeotropes (MCS)) [°C]

252

Pressure (Azeotropes (MCS)) [Torr]

760

Azeotropes

eugenol

Temperature (Azeotropes (MCS)) [°C]

251.3

Pressure (Azeotropes (MCS)) [Torr]

760

Azeotropes

phenylacrolein

Temperature (Azeotropes (MCS)) [°C]

248.6

Pressure (Azeotropes (MCS)) [Torr]

760

Azeotropes

anisaldehyde

Temperature (Azeotropes (MCS)) [°C]

214

Pressure (Azeotropes (MCS)) [Torr]

760

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Azeotropes

acetamide

Temperature (Azeotropes (MCS)) [°C]

218.5

Pressure (Azeotropes (MCS)) [Torr]

760

Azeotropes

propionamide

Temperature (Azeotropes (MCS)) [°C]

246.5

Pressure (Azeotropes (MCS)) [Torr]

760

Azeotropes

benzoic acid

Temperature (Azeotropes (MCS)) [°C]

250.8

Pressure (Azeotropes (MCS)) [Torr]

760

Azeotropes

phenylacetic acid

Temperature (Azeotropes (MCS)) [°C]

248.8

Pressure (Azeotropes (MCS)) [Torr]

760

Azeotropes

p-phenetidine

Lecat,M.; Ann. Soc. scient. Bruxelles; vol. 48; p. 19,54,118, 120, 122, 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; Lecat,M.; Tables azeotropiques, 2. Aufl. Bd. I <Uccle-Bruxelles 1949>, S. 27, 109, 111, 159, 163, 171, 172, 188, 219, 333, View in Reaxys Chromatographic Data (1) Chromatographic References data GC (Gas chroma- Jeon, Ju-Hyun; Yang, Ji-Yeon; Chung, Namhyun; Lee, Hoi-Seon; Journal of Agricultural and Food Chemtography) istry; vol. 60; nb. 50; (2012); p. 12349 - 12354, View in Reaxys Dynamic Viscosity (1) Dynamic Viscosi- Temperature (Dyty [P] namic Viscosity) [°C] 0.0398

References

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

Electrochemical Characteristics (1) 1 of 1

Description (Electrochemical Characteristics)

oxidation potential

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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 Further Information (2) Description (Fur- References ther Information) Further information

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

Further information

Sawicki et al.; Analytical Chemistry; vol. 34; (1962); p. 1460,1461, View in Reaxys

Optics (1) Description (Optics) Magnetic birefringence (CottonMouton effect)

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

Transport Phenomena (MCS) (1) 1 of 1

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 (4) 1 of 4

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

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

400

Location

supporting information

Perdriau, Sbastien; Chang, Mu-Chieh; Otten, Edwin; Heeres, Hero J.; De Vries, Johannes G.; Chemistry - A European Journal; vol. 20; nb. 47; (2014); p. 15434 - 15442, View in Reaxys 2 of 4

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

13C

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

101

Location

supporting information

Perdriau, Sbastien; Chang, Mu-Chieh; Otten, Edwin; Heeres, Hero J.; De Vries, Johannes G.; Chemistry - A European Journal; vol. 20; nb. 47; (2014); p. 15434 - 15442, View in Reaxys 3 of 4

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

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

400

Buchanan, Hilary A. S.; Daeid, Niamh Nic; Meier-Augenstein, Wolfram; Kemp, Helen F.; Kerr, William J.; Middleditch, Michael; Analytical Chemistry; vol. 80; nb. 9; (2008); p. 3350 - 3356, View in Reaxys 4 of 4

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

13C

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

100

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CH2Cl2

Description (IR Spectroscopy)

Bands

Cabiddu et al.; Annali di Chimica (Rome, Italy); vol. 52; (1962); p. 1261,1263, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) gas chromatogra- supporting inforphy mass specmation trometry (GCMS); electron impact (EI); spectrum

References Jeon, Ju-Hyun; Yang, Ji-Yeon; Chung, Namhyun; Lee, Hoi-Seon; Journal of Agricultural and Food Chemistry; vol. 60; nb. 50; (2012); p. 12349 - 12354, View in Reaxys

UV/VIS Spectroscopy (3) 1 of 3

Description (UV/VIS Spectroscopy)

UV/VIS

Walterova et al.; Collection of Czechoslovak Chemical Communications; vol. 39; (1974); p. 2449,2451, View in Reaxys; Melhuish; Miller; Australian Journal of Chemistry; vol. 31; (1978); p. 795,796-801, View in Reaxys 2 of 3

Description (UV/VIS Spectroscopy)

Spectrum

Ramart-Lucas; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 188; (1929); p. 639, View in Reaxys 3 of 3

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

ethanol

Crymble; Stewart; Wright; Glendinning; Journal of the Chemical Society; vol. 99; (1911); p. 457, View in Reaxys Fluorescence Spectroscopy (1) Description (Fluo- References rescence Spectroscopy) Fluorescence

Melhuish; Miller; Australian Journal of Chemistry; vol. 31; (1978); p. 795,796-801, View in Reaxys

Phosphorescence Spectroscopy (1)

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Description (Phosphorescence Spectroscopy)

References

Phosphorescence Melhuish; Miller; Australian Journal of Chemistry; vol. 31; (1978); p. 795,796-801, View in Reaxys Pharmacological Data (32) 1 of 32

Comment (Pharmacological Data)

Bioactivities present

Patent; Rhone-Poulenc S. A.; US4138411; (1979); (A1) English, View in Reaxys; Klamann,D. et al.; Chemische Berichte; vol. 98; (1965); p. 1831 - 1836, View in Reaxys; Williams,J.K. et al.; Journal of the American Chemical Society; vol. 84; (1962); p. 2210 - 2215, View in Reaxys; Barton,D.H.R.; Jones,D.W.; Journal of the Chemical Society; (1965); p. 3563 - 3570, View in Reaxys; Cabiddu,S. et al.; Gazzetta Chimica Italiana; vol. 98; (1968); p. 800 809, View in Reaxys; Moureu; Bulletin de la Societe Chimique de France; vol. <3> 15; (1896); p. 655; Annales de Chimie (Cachan, France); vol. <7> 18; (1899); p. 104, View in Reaxys; Robinson; Journal of the Chemical Society; vol. 107; (1915); p. 267, View in Reaxys; Foulds; Robinson; Journal of the Chemical Society; vol. 105; (1914); p. 1966, View in Reaxys; Boettcher; Chemische Berichte; vol. 42; (1909); p. 256, View in Reaxys; Henrard; Chem. Zentralbl.; vol. 78; nb. II; (1907); p. 1512, View in Reaxys; Schimmel and Co.; Chem. Zentralbl.; vol. 76; nb. I; (1905); p. 1470, View in Reaxys; Patent; Merck; DE274350; Fortschr. Teerfarbenfabr. Verw. 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View in Reaxys; Shulgin; J. Chromatographie; vol. 30; (1967); p. 54,60, View in Reaxys; LoraTamayo; Madronero; Rev. Acad. Cienc. exact. fis. nat. Madrid; vol. 53; (1959); p. 527,536, 538, View in Reaxys; Lora-Tamayo; Madronero; Rev. Acad. Cienc. exact. fis. nat. Madrid; vol. 53; (1959); p. 527,536-538, View in Reaxys; Nguyen, Tien M.; Manohar, Namita; Nicewicz, David A.; Angewandte Chemie - International Edition; vol. 53; nb. 24; (2014); p. 6198 - 6201; Angew. Chem.; vol. 126; nb. 24; (2014); p. 6312 - 6315,4, View in Reaxys; Tomita, Ren; Yasu, Yusuke; Koike, Takashi; Akita, Munetaka; Angewandte Chemie - International Edition; vol. 53; nb. 28; (2014); p. 7144 7148; Angew. Chem.; vol. 126; nb. 28; (2014); p. 7272 - 7276,5, View in Reaxys; Upadhyay, Praveenkumar; Srivastava, Vivek; RSC Advances; vol. 5; nb. 1; (2015); p. 740 - 745, View in Reaxys; Ou, Wenhua; Huang, Hong; Asian Journal of Chemistry; vol. 27; nb. 3; (2015); p. 1175 - 1176, View in Reaxys; Sada, Nagisa; Lee, Suni; Katsu, Takashi; Otsuki, Takemi; Inoue, Tsuyoshi; Science; vol. 347; nb. 6228; (2015); p. 1362 - 1367, View in Reaxys; Zeller, Mary A.; Riener, Michelle; Nicewicz, David A.; Organic Letters; vol. 16; nb. 18; (2014); p. 4810 - 4813, 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; Akita, Munetaka; Koike, Takashi; Comptes Rendus Chimie; vol. 18; nb. 7; (2015); p. 742 - 751, View in Reaxys; Sharma, Rohit; Abbat, Sheenu; Mudududdla, Ramesh; Vishwakarma, Ram A.; Bharatam, Prasad V.; Bharate, Sandip B.; Tetrahedron Letters; vol. 56; nb. 27; (2015); p. 4057 - 4059; Art.No: 46211, View in Reaxys; Patent; BioDiem, Ltd; Denisenko, Peter Prokofievich; Sapronov, Nikolay Sergeevich; Tarasenko, Alexander Alexandrovich; US2015/258059; (2015); (A1) English, View in Reaxys; Perdriau, Sbastien; Chang, Mu-Chieh; Otten, Edwin; Heeres, Hero J.; De Vries, Johannes G.; Chemistry - A European Journal; vol. 20; nb. 47; (2014); p. 15434 - 15442, View in Reaxys 2 of 32

Comment (Pharmacological Data)

physiological behaviour discussed

Sada, Nagisa; Lee, Suni; Katsu, Takashi; Otsuki, Takemi; Inoue, Tsuyoshi; Science; vol. 347; nb. 6228; (2015); p. 1362 - 1367, View in Reaxys 3 of 32

Effect (Pharmacological Data)

toxic

Species or Test-System (Pharmacological Data)

Dermatophagoides farinae, mites

Concentration (Pharmacological Data)

2.5 - 39 μg/cm2

Method (Pharmacological Data)

name of assay/method: fumigant toxicity bioassay

Type (Pharmacological Data)

mortality rate

Value of Type (Pharmacological Data)

13.2 - 83.5 percent

Jeon, Ju-Hyun; Yang, Ji-Yeon; Chung, Namhyun; Lee, Hoi-Seon; Journal of Agricultural and Food Chemistry; vol. 60; nb. 50; (2012); p. 12349 - 12354, View in Reaxys 4 of 32

Effect (Pharmacological Data)

toxic

Species or Test-System (Pharmacological Data)

Dermatophagoides pteronyssinus, mites

Concentration (Pharmacological Data)

2.5 - 39 μg/cm2

Method (Pharmacological Data)

name of assay/method: fumigant toxicity bioassay

Type (Pharmacological Data)

mortality rate

Value of Type (Pharmacological Data)

11.2 - 91.2 percent

Jeon, Ju-Hyun; Yang, Ji-Yeon; Chung, Namhyun; Lee, Hoi-Seon; Journal of Agricultural and Food Chemistry; vol. 60; nb. 50; (2012); p. 12349 - 12354, View in Reaxys 5 of 32

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

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Type (Pharmacological Data)

percent mortality

Value of Type (Pharmacological Data)

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 6 of 32

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)

0.6 - 2.1 μg/cm2

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 7 of 32

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 8 of 32

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-Al-

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da-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) = ~200 (substrate: acetaldehyde), ~99 (substrate: phenylacetaldehyde) at 50 μM

Location

Page/Page column 1; 49-50

Patent; Mochly-Rosen, Daria; Chen, Che-Hong; Yang, Wenjin; US2010/113423; (2010); (A1) English, View in Reaxys 9 of 32

Effect (Pharmacological Data)

hepatoprotective

Species or Test-System (Pharmacological Data)

XVIInc/Z mice

Sex

female

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

150 mg/kg

Kind of Dosing (Pharmacological Data)

test comp. dissolv. in olive oil; admin. daily for 4 days

Exposure Period (Pharmacological Data)

Method (Pharmacological Data)

homozygous mice aged 3 months; treat. with 0.1 μM 5,9-diMeDBC for 48 h after 4 d tretreatm. with test comp.; kill. by cervical dislocation; livers homogen.; DNA extract.; (32P)postlabel. assay of adducts; autoradiography; immunoblot analysis

Further Details (Pharmacological Data)

kept under standard conditions; 20 deg C; relat. humid. 50 percent; 12-h light/dark cycle; 5,9-diMeDBC= 5,9-dimethyldibenzo(c,g)carbazole

Results

100 percent inhibition of 5,9-diMeDBC-DNA adduct formation; no induction of CYP1A1; induction of CYP1A2

Taras-Valero, Daniele; Perin-Roussel, Odette; Plessis, Marie-Jose; Perin, Francois; Environmental and Molecular Mutagenesis; vol. 32; nb. 4; (1998); p. 314 - 324, View in Reaxys 10 of 32

Effect (Pharmacological Data)

hepatoprotective

Species or Test-System (Pharmacological Data)

DBA/2N mice

Sex

female

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

150 mg/kg

Kind of Dosing (Pharmacological Data)

test comp. dissolv. in olive oil; admin. daily for 4 days

Exposure Period (Pharmacological Data)

Method (Pharmacological Data)

Further Details (Pharmacological Data)

kept under standard conditions; 20 deg C; relat. humid. 50 percent; 12-h light/dark cycle; 5,9-diMeDBC= 5,9-dimethyldibenzo(c,g)carbazole

Results

ca. 65 percent inhibition of 5,9-diMeDBC-DNA adduct formation; no induction of CYP1A1; induction of CYP1A2

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Taras-Valero, Daniele; Perin-Roussel, Odette; Plessis, Marie-Jose; Perin, Francois; Environmental and Molecular Mutagenesis; vol. 32; nb. 4; (1998); p. 314 - 324, View in Reaxys 11 of 32

Effect (Pharmacological Data)

hepatotoxic

Species or Test-System (Pharmacological Data)

DBA/2N mice

Sex

female

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

150 mg/kg

Kind of Dosing (Pharmacological Data)

test comp. dissolv. in olive oil; 2 daily injections

Exposure Period (Pharmacological Data)

48 h

Method (Pharmacological Data)

homozygous mice aged 3 months; kill. by cervical dislocation; livers homogen.; GST and UDPGT activities; bromodeoxyuridine (BrdU) labeling indices

Further Details (Pharmacological Data)

kept under standard conditions; 20 deg C; relat. humid. 50 percent; 12-h light/dark cycle; GST=glutathione-S-transferase; UDPGT=uridine diphosphoglucuronyl transferase

Results

activ. of GST and UDPGT signif. increas.; very weak level of label. hepatocytes; no induction of DNA synthesis

Taras-Valero, Daniele; Perin-Roussel, Odette; Plessis, Marie-Jose; Perin, Francois; Environmental and Molecular Mutagenesis; vol. 32; nb. 4; (1998); p. 314 - 324, View in Reaxys 12 of 32

Effect (Pharmacological Data)

hepatotoxic

Species or Test-System (Pharmacological Data)

XVIInc/Z mice

Sex

female

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

150 mg/kg

Kind of Dosing (Pharmacological Data)

test comp. dissolv. in olive oil; 2 daily injections

Exposure Period (Pharmacological Data)

48 h

Method (Pharmacological Data)

homozygous mice aged 3 months; kill. by cervical dislocation; livers homogen.; GST and UDPGT activities; bromodeoxyuridine (BrdU) labeling indices

Further Details (Pharmacological Data)

kept under standard conditions; 20 deg C; relat. humid. 50 percent; 12-h light/dark cycle; GST=glutathione-S-transferase; UDPGT=uridine diphosphoglucuronyl transferase

Results

weak increase in activ. of GST and UDPGT (1.1-fold); very weak level of label. hepatocytes; no induction of DNA synthesis

Taras-Valero, Daniele; Perin-Roussel, Odette; Plessis, Marie-Jose; Perin, Francois; Environmental and Molecular Mutagenesis; vol. 32; nb. 4; (1998); p. 314 - 324, View in Reaxys 13 of 32

Effect (Pharmacological Data)

enzyme; induction of

Species or Test-System (Pharmacological Data)

human Hela cells

Method (Pharmacological Data)

cells cultured in Dulbecco's Modified Eagle's Medium, 6.2-617 μM title comp.; total RNA isolated; P450 1A1 mRNA quantified

Further Details (Pharmacological Data)

maximal induction of cytochrome P450 1A1 mRNA (Imax), concentration of half-maximal induction (IM)

Results

Imax: 0.12E6 mRNA molecules/150 ng, IM: 275 μM

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Froetschl, Roland; Chichmanov, Lubomir; Kleeberg, Ullrich; Hildebrandt, Alfred G.; Roots, Ivar; Brockmoeller, Juergen; Chemical Research in Toxicology; vol. 11; nb. 12; (1998); p. 1447 - 1452, View in Reaxys 14 of 32

Effect (Pharmacological Data)

enzyme; induction of

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

450 mg/kg

Method (Pharmacological Data)

in vivo; animals were injected with 150 mg/kg of title compound three times for 3 days; at 24 h after last treatment hepatocytes were isolated; incubation at 37 deg C; CYP1A1, CYP1A2, NAT1, NAT2 activities determination; colorimetric method

Results

title compound exposure led to increase of the CYP1A1 and CYP1A2 activities but the NAT1 and NAT2 activities remained unchanged

Padma, Palghat Raghunathan; Oesch-Bartlomowicz, Barbara; Hengstler, Jan Georg; Oesch, Franz; Archives of Toxicology; vol. 71; nb. 10; (1997); p. 655 - 659, View in Reaxys 15 of 32

Effect (Pharmacological Data)

enzyme; examination of

Species or Test-System (Pharmacological Data)

human hepatocyte HHO9i microsomes

Sex

male

Concentration (Pharmacological Data)

<= 500 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in methanol

Method (Pharmacological Data)

distinction of CYP1A1 and CYP2A2 activity in microsomes by selective inhibition using title comp.; title comp. incubated with ER and microsomes at pH 7.6; EROD measured spectrophotometrically; control: without title comp.

Further Details (Pharmacological Data)

ER: 7-ethoxyresorufin, 0.17 and 0.42 μmol/l tested; EROD: ER O-deethylation

Results

at title comp. conc. 2-10 μmol/l, calculated CYP1A1 and CYP1A2 activities were relatively independent; at 5 μmol/l, levels of CYP1A2 and CYP1A1 EROD activities: 14.0 and 8.5 pmol/mg protein, resp. (figures)

Pastrakuljic, Aleksandra; Tang, Bing K.; Roberts, Eve A.; Kalow, Werner; Biochemical Pharmacology; vol. 53; nb. 4; (1997); p. 531 - 538, View in Reaxys 16 of 32

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

human liver microsomes expressing CYP1A2

Concentration (Pharmacological Data)

<= 500 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in methanol

Method (Pharmacological Data)

inhibitory effect of title comp. on EROD activity of CYP1A2 with ER as substrate; inhibition kinetics; title comp. incubated with ER and microsomal protein in buffer at pH 7.6; EROD measured spectrophotometrically; control: without title comp.

Further Details (Pharmacological Data)

ER: 7-ethoxyresorufin, 0.17 and 0.42 μmol/l tested; EROD: ER O-deethylation

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

0.6 μmol/l

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Results

Ki = 700 nmol/l; inhibition with title comp. was consistent with competitive type (table, figure)

Pastrakuljic, Aleksandra; Tang, Bing K.; Roberts, Eve A.; Kalow, Werner; Biochemical Pharmacology; vol. 53; nb. 4; (1997); p. 531 - 538, View in Reaxys 17 of 32

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

human liver microsomes expressing CYP1A1

Concentration (Pharmacological Data)

<= 500 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in methanol

Method (Pharmacological Data)

inhibitory effect of title comp. on EROD activity of CYP1A1 with ER as substrate; inhibition kinetics; title comp. incubated with ER and microsomal protein in buffer at pH 7.6; EROD measured spectrophotometrically; control: without title comp.

Further Details (Pharmacological Data)

ER: 7-ethoxyresorufin, 0.17 and 0.42 μmol/l tested; EROD: ER O-deethylation

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

11 μmol/l

Results

Ki = 10000 nmol/l; inhibition with title comp. was consistent with competitive type (table, figure)

Pastrakuljic, Aleksandra; Tang, Bing K.; Roberts, Eve A.; Kalow, Werner; Biochemical Pharmacology; vol. 53; nb. 4; (1997); p. 531 - 538, View in Reaxys 18 of 32

Effect (Pharmacological Data)

enzyme; examination of

Species or Test-System (Pharmacological Data)

human liver microsomes

Concentration (Pharmacological Data)

<= 500 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in methanol

Method (Pharmacological Data)

Further Details (Pharmacological Data)

ER: 7-ethoxyresorufin, 0.17 and 0.42 μmol/l tested; EROD: ER O-deethylation; microsomes from surplus portions of livers used for segmental liver transplants

Results

at title comp. concentrations 2-10 μmol/l, calculated CYP1A1 and CYP1A2 activities were relatively independent; at 5 μmol/l, levels of CYP1A2 and CYP1A1 EROD activity ranged from 45.3 to 75.8 and from 0.4 to 2.7 pmol/mg protein, resp. (figures)

Pastrakuljic, Aleksandra; Tang, Bing K.; Roberts, Eve A.; Kalow, Werner; Biochemical Pharmacology; vol. 53; nb. 4; (1997); p. 531 - 538, View in Reaxys 19 of 32

Effect (Pharmacological Data)

enzyme; induction of

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

150 mg/kg

Kind of Dosing (Pharmacological Data)

dosage as mg/kg body weight; solution in sunflower oil

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Exposure Period (Pharmacological Data)

Method (Pharmacological Data)

rat weight 250-325 g; housed 2-3/cage; free access to water and food; liver excised; parenchymal and nonparenchymal cells isolated on day 4; microsomes prepared

Further Details (Pharmacological Data)

microsomes incubated with 16 and 128 μM aflatoxin B1 for 15 min; AFB1-9a-hydroxylase activity; formation of AFM1, AFQ1, AFB1-E metabolites formation in microsomes

Results

AFB1-9a-hydroxylase activity induced in parenchymal and nonparenchymal cells; enhanced formation rate of AFM1, AFQ1, AFB1-E in parenchymal cells; AFM1, AFQ1 and AFB1-E formation signif. increased in nonparenchymal cells

Gemechu-Hatewu, M.; Platt, K.-L.; Oesch, F.; Steinberg, P.; Archives of Toxicology; vol. 70; nb. 9; (1996); p. 553 558, View in Reaxys 20 of 32

Effect (Pharmacological Data)

effect on protein expression

Species or Test-System (Pharmacological Data)

human colon adenocarcinoma LS180/AD50 cells

Concentration (Pharmacological Data)

10 μmol/l

Exposure Period (Pharmacological Data)

48 - 72 h

Method (Pharmacological Data)

cells treated with/without (control) title comp. then harvested

Further Details (Pharmacological Data)

amounts of P-glycoprotein (Pgp), cytochromes P450 (CYP) 3A4 and 3A5 quantified by immunoblot analysis

Results

title comp. increased Pgp (2.7-fold) and CYP3As (2.6-fold) expression

Schuetz, Erin G.; Beck, William T.; Schuetz, John D.; Molecular Pharmacology; vol. 49; nb. 2; (1996); p. 311 318, View in Reaxys 21 of 32

Effect (Pharmacological Data)

enzyme; examination of

Endpoint of Effect (Pharmacological Data)

cytochrome P450 enzymes activity

Species or Test-System (Pharmacological Data)

New Zealand rabbit

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

150 mg/kg/d

Kind of Dosing (Pharmacological Data)

in corn oil

Exposure Period (Pharmacological Data)

Method (Pharmacological Data)

rabbits weighing ca. 2.5 kg; liver microsomes; Western-blot analysis: specific contents of CYP1A1/2, 2B4, 3A6, 2A1/2 and 4A1; effect on cytochrome P450-dependent monooxygenase activitie (EROD, PROD, COH, ETND)

Further Details (Pharmacological Data)

EROD: ethoxyresorufin O-deethylase; PROD: pentoxyresorufin O-depentylase; COH: coumarin 7-hydroxylase; ETND: ethylmorphine N-demethylase

Results

significant effects: decrease in COH (168 pmol/mg protein/min; control: 340) activity, 29 percent increase in CYP1A2 level

Rey-Grobellet; Eeckhoutte; Sutra; Alvinerie; Galtier; Xenobiotica; vol. 26; nb. 7; (1996); p. 765 - 778, View in Reaxys 22 of 32

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)

20 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 23 of 32

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)

230 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 24 of 32

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)

76 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 25 of 32

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)

110 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 26 of 32

Effect (Pharmacological Data)

drug interaction

Species or Test-System (Pharmacological Data)

DBA/2N mice

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

150 mg/kg

Kind of Dosing (Pharmacological Data)

one injection for four days

Method (Pharmacological Data)

10 mg/kg 2-amino-3,8-dimethyl-imidazol<4,5-f>quinoxaline (MeIQx) administered by gavage; animals were sacrificed, organs removed; radioactivity measurements

Further Details (Pharmacological Data)

effect on time dependent organ distribution of MeIQx

Results

slightly increased microsomal activating capacity

Vikse; Ingebrigsten; Klungsoyr; Alexander; Pharmacology and Toxicology; vol. 77; nb. 1; (1995); p. 57 - 64, View in Reaxys 27 of 32

Effect (Pharmacological Data)

drug interaction

Species or Test-System (Pharmacological Data)

BLJ57/6J mice

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

150 mg/kg

Kind of Dosing (Pharmacological Data)

one injection for four days

Method (Pharmacological Data)

10 mg/kg 2-amino-3,8-dimethyl-imidazol<4,5-f>quinoxaline (MeIQx) administered by gavage; animals were sacrificed, organs removed; radioactivity measurements

Further Details (Pharmacological Data)

effect on time dependent organ distribution of MeIQx

Results

slightly increased microsomal activating capacity

Vikse; Ingebrigsten; Klungsoyr; Alexander; Pharmacology and Toxicology; vol. 77; nb. 1; (1995); p. 57 - 64, View in Reaxys 28 of 32

Effect (Pharmacological Data)

activation of chloroxazone 6-hydroxylation

Species or Test-System (Pharmacological Data)

Sprague-Dawley rats

Sex

male and female

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

150 mg/kg/day

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Exposure Period (Pharmacological Data)

Method (Pharmacological Data)

adult rats pretreated with title compd., decapitated 24 h after last treatment; hepatic microsomes prepn., incubation with 2 or 200 μM chloroxazone (20 min); HPLC anal.

Results

sex- and chloroxazone-concn.-dependent kinetic parameters (Vmax = 3.66 - 71.2 pmol/min/mg) evaluated (table)

Jayyosi; Knoble; Muc; Erick; Thomas; Kelley; Journal of Pharmacology and Experimental Therapeutics; vol. 273; nb. 3; (1995); p. 1156 - 1161, View in Reaxys 29 of 32

Effect (Pharmacological Data)

enzyme; examination of

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Concentration (Pharmacological Data)

200 mg/kg/d

Exposure Period (Pharmacological Data)

Method (Pharmacological Data)

weight 240-260 g; effects of title comp. on P450-dependent metabolism of theophylline by rat liver microsomes; rats were killed 1 d after a last dose of title comp.

Further Details (Pharmacological Data)

liver microsomal protein 2 mg/ml; NADPH-regenerating system; Tris buffer 0.1 M, pH 7.4; 37 deg C; theophylline 25 mM; 1 h

Results

increased the rate of 1,3-dimethylureic acid production (ca. 2.5-fold), small effect on 1methylxanthine production

Davis; Aarons; Houston; Xenobiotica; vol. 25; nb. 6; (1995); p. 563 - 573, View in Reaxys 30 of 32

Effect (Pharmacological Data)

inhibition of ECOD activity

Species or Test-System (Pharmacological Data)

Wistar rat

Concentration (Pharmacological Data)

100 μmol/l

Method (Pharmacological Data)

male rats pretreated with phenobarbital i.p at dose 80 mg/kg/day for 3 days; starved for 12 h; sacrificed 24 h after last injection; liver removed, homogenated; assay mixture for ECOD activity: Tris-HCl, 7-ethoxycoumarin, NADPH, microsomal protein

Further Details (Pharmacological Data)

ECOD - 7-ethoxycoumarin O-deethylase

Type (Pharmacological Data)

inhibition constant

Value of Type (Pharmacological Data)

9.28 μmol/l

Hanioka, Nobumitsu; Jinno, Hideto; Toyo'oka, Toshimasa; Kojima, Shigeo; Ando, Masanori; Chemosphere; vol. 28; nb. 9; (1994); p. 1589 - 1598, View in Reaxys 31 of 32

Effect (Pharmacological Data)

inhibition of ECOD activity

Species or Test-System (Pharmacological Data)

Wistar rat

Concentration (Pharmacological Data)

100 μmol/l

Method (Pharmacological Data)

male rats pretreated with 3-methylcholanthrene i.p at dose 20 mg/kg/day for 3 days; starved for 12 h; sacrified 24 h after last injection; liver removed, homogenated; assay mixture for ECOD activity: Tris-HCl, 7-ethoxycoumarin, NADPH, microsomal protein

Further Details (Pharmacological Data)

ECOD - 7-ethoxycoumarin O-deethylase

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Type (Pharmacological Data)

inhibition constant

Value of Type (Pharmacological Data)

14.9 μmol/l

Hanioka, Nobumitsu; Jinno, Hideto; Toyo'oka, Toshimasa; Kojima, Shigeo; Ando, Masanori; Chemosphere; vol. 28; nb. 9; (1994); p. 1589 - 1598, View in Reaxys 32 of 32

Comment (Pharmacological Data)

substrate to inhibition assay in ABA biosynthesis; conc: c = 100 μM, inhibition: (I) = 21 percent;

Norman Poling; Maier; Pon; Agricultural and Biological Chemistry; vol. 52; nb. 5; (1988); p. 1309 - 1310, View in Reaxys Ecotoxicology (3) 1 of 3

Effect (Ecotoxicology)

insecticidal

Endpoint of Effect (Ecotoxicology)

mortality

Species or Test-System (Ecotoxicology)

Sitophilus oryzae, rice weevil

Method (Ecotoxicology)

20 adult insects (10-15 d) in cages; mortality determination after 24 h of treatment; fumigation chamber volume 3.4 l; test fumigant material deposited on a piece of filter paper

Type (Ecotoxicology)

LC50

Value of Type (Ecotoxicology)

19.3 μl/l air

Lee, Sung-Eun; Lee, Byoung-Ho; Choi, Won-Sik; Park, Byeoung-Soo; Kim, Jeong-Gyu; Campbell, Bruce C.; Pest Management Science; vol. 57; nb. 6; (2001); p. 548 - 553, View in Reaxys 2 of 3

Effect (Ecotoxicology)

insecticidal

Endpoint of Effect (Ecotoxicology)

mortality

Species or Test-System (Ecotoxicology)

Sitophilus oryzae, rice weevil

Method (Ecotoxicology)

20 adult insects (10-15 d) in cages; mortality determination after 24 h of treatment; fumigation chamber volume 3.4 l; test fumigant material deposited on a piece of filter paper

Type (Ecotoxicology)

LC95

Value of Type (Ecotoxicology)

78.3 μl/l air

Lee, Sung-Eun; Lee, Byoung-Ho; Choi, Won-Sik; Park, Byeoung-Soo; Kim, Jeong-Gyu; Campbell, Bruce C.; Pest Management Science; vol. 57; nb. 6; (2001); p. 548 - 553, View in Reaxys 3 of 3

Effect (Ecotoxicology)

enzyme; inhibition of

Species or Test-System (Ecotoxicology)

Sitophilus oryzae, rice weevil

Method (Ecotoxicology)

solution of acetylcholinesterase from adult insects (100 μl), acetylcholine iodide (0.5 mM), 5,5'-dithiobis(2-nitrobenzoic acid) (0.33 mM), phosphate buffer (92.7 mM) and test compound incubated at 25 deg C for 5 min; UV-estimation of thiocholine level

Type (Ecotoxicology)

Value of Type (Ecotoxicology)

0.71 mmol/l

Lee, Sung-Eun; Lee, Byoung-Ho; Choi, Won-Sik; Park, Byeoung-Soo; Kim, Jeong-Gyu; Campbell, Bruce C.; Pest Management Science; vol. 57; nb. 6; (2001); p. 548 - 553, View in Reaxys Isolation from Natural Product (3) Isolation from Comment (IsolaNatural Product tion from Natural Product)

References

aus Petersiliensamenoel nach Δ

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

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mit aethanol. KOH Isolierung aus dem aetherischen Oel der Blaetter von Murraya koenigii.

isosafrole-substances of uncertain configurative homogeneity

Dutt; Indian Soap J.; vol. 23; (1958); p. 201,205, View in Reaxys

Isolierung aus dem aetherischen Oel der Wurzeln von Ligusticum acutilobum.

isosafrole-substances of uncertain configurative homogeneity

Noguchi et al.; Yakugaku Zasshi; vol. 57; (1937); p. 769,773; dtsch. Ref. S. 187; Chem.Abstr.; (1938); p. 3360, View in Reaxys

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