Melting point	219-223 ºC

Symbol(GHS)	Xi
Hazard Codes	R36/37/38
SDS/MSDS	S26;S36

Source	SDS/MSDS Samples
Sigma-Aldrich	View & Download
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Acros-Organics	View & Download

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Peer-Reviewed Papers

Modified expression of aryl hydrocarbon receptor-related genes by deoxymiroestrol, a phytoestrogen, in mouse hepatocytes in primary culture.Latiporn Udomsuk et al.Journal of ethnopharmacology, 137(1), 902-908 (2011-07-23) Modulation of aryl hydrocarbon receptor regulated genes by acute administration of trimethylarsine oxide in the lung, kidney and heart of C57BL/6 mice.Osama H Elshenawy et al.Xenobiotica; the fate of foreign compounds in biological systems, 45(10), 930-943 (2015-06-05) Structural features of cytochrome P450 1A associated with the absence of EROD activity in liver of the loricariid catfish Pterygoplichthys sp.Thiago E M Parente et al.Gene, 489(2), 111-118 (2011-08-16) Reduction of resazurin to resorufin catalyzed by gold nanoparticles: dramatic reaction acceleration by laser or LED plasmon excitationAlejo CJ, et al. Catalysis Science & Technology, 1(8), 1506-1511 (2011) Methoxyresorufin: an inappropriate substrate for CYP1A2 in the mouse.J T Hamm et al.Biochemical pharmacology, 56(12), 1657-1660 (1999-02-11) Sex-specific differences in hyperoxic lung injury in mice: role of cytochrome P450 (CYP)1A.Krithika Lingappan et al.Toxicology, 331, 14-23 (2015-02-24) Expression of aryl hydrocarbon receptor 1 (AHR1), AHR1 nuclear translocator 1 (ARNT1) and CYP1 family monooxygenase mRNAs and their activity in chicken ovarian follicles following in vitro exposure to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD).Piotr A Antos et al.Toxicology letters, 237(2), 100-111 (2015-06-06) Immunochemical detection of cytochrome P450 enzymes in liver microsomes of 27 cynomolgus monkeys.Shotaro Uehara et al.The Journal of pharmacology and experimental therapeutics, 339(2), 654-661 (2011-08-19) Analysis of the AHR gene proximal promoter GGGGC-repeat polymorphism in lung, breast, and colon cancer.Barbara C Spink et al.Toxicology and applied pharmacology, 282(1), 30-41 (2014-12-03) Inhibition of cytochrome P450 1A2-mediated metabolism and production of reactive oxygen species by heme oxygenase-1 in rat liver microsomes.James R Reed et al.Drug metabolism letters, 5(1), 6-16 (2010-10-15) Structural features of cytochrome P450 1A associated with the absence of EROD activity in liver of the loricariid catfish Pterygoplichthys sp.Thiago E M Parente et al.Gene, 489(2), 111-118 (2011-08-16) Reduction of resazurin to resorufin catalyzed by gold nanoparticles: dramatic reaction acceleration by laser or LED plasmon excitationAlejo CJ, et al. Catalysis Science & Technology, 1(8), 1506-1511 (2011) Lack of constitutive and inducible ethoxyresorufin-O-deethylase activity in the liver of suckermouth armored catfish (Hypostomus affinis and Hypostomus auroguttatus, Loricariidae).T E M Parente et al.Comparative biochemistry and physiology. Toxicology & pharmacology : CBP, 150(2), 252-260 (2009-05-23) Potent inhibition of CYP1A2 by Frutinone A, an active ingredient of the broad spectrum antimicrobial herbal extract from P. fruticosa.Roslyn S Thelingwani et al.Xenobiotica; the fate of foreign compounds in biological systems, 42(10), 989-1000 (2012-04-27) Inhibition of rat liver cytochrome P450 isozymes by isothiocyanates and their conjugates: a structure-activity relationship study.C C Conaway et al.Carcinogenesis, 17(11), 2423-2427 (1996-11-01) Maternal obesity alters feto-placental cytochrome P4501A1 activity.B N DuBois et al.Placenta, 33(12), 1045-1051 (2012-10-11) Differential inducing effect of benzo[a]pyrene on gene expression and enzyme activity of cytochromes P450 1A1 and 1A2 in Sprague-Dawley and Wistar rats.Maura Floreani et al.Drug metabolism and pharmacokinetics, 27(6), 640-652 (2012-07-13) Human health risk assessment of soil dioxin/furans contamination and dioxin-like activity determined by ethoxyresorufin-O-deethylase bioassay.Yu Bon Man et al.Environmental science and pollution research international, 22(7), 5218-5227 (2014-12-10) Potentiating effect of graphene nanomaterials on aromatic environmental pollutant-induced cytochrome P450 1A expression in the topminnow fish hepatoma cell line PLHC-1.Tobias Lammel et al.Environmental toxicology, 30(10), 1192-1204 (2014-04-08) Effects of BDE-209 and its mixtures with BDE-47 and BDE-99 on multiple biomarkers in Carassius auratus.Zhengxin Xie et al.Environmental toxicology and pharmacology, 38(2), 554-561 (2014-09-03) Activation of the aryl hydrocarbon receptor by the widely used Src family kinase inhibitor 4-amino-5-(4-chlorophenyl)-7-(dimethylethyl)pyrazolo[3,4-d]pyrimidine (PP2).Katrin Frauenstein et al.Archives of toxicology, 89(8), 1329-1336 (2014-08-02) The effect of cloudy apple juice on hepatic and mammary gland phase I and II enzymes induced by DMBA in female Sprague-Dawley rats.Hanna Szaefer et al.Drug and chemical toxicology, 37(4), 472-479 (2014-03-04) Identification of mitochondrial cytochrome P450 induced in response to polycyclic aromatic hydrocarbons in the mummichog (Fundulus heteroclitus).Dawoon Jung et al.Comparative biochemistry and physiology. Toxicology & pharmacology : CBP, 151(1), 107-112 (2009-09-18) Novel Marmoset Cytochrome P450 2C19 in Livers Efficiently Metabolizes Human P450 2C9 and 2C19 Substrates, S-Warfarin, Tolbutamide, Flurbiprofen, and Omeprazole.Shotaro Uehara et al.Drug metabolism and disposition: the biological fate of chemicals, 43(10), 1408-1416 (2015-08-01) Interference with xenobiotic metabolic activity by the commonly used vehicle solvents dimethylsulfoxide and methanol in zebrafish (Danio rerio) larvae but not Daphnia magna.Rhiannon M David et al.Chemosphere, 88(8), 912-917 (2012-04-05) CYP1B1 detection.Rao L Divi et al.Current protocols in toxicology, Chapter 4, Unit 4-Unit 4 (2012-04-19) ahr2, But Not ahr1a or ahr1b, Is Required for Craniofacial and Fin Development and TCDD-dependent Cardiotoxicity in Zebrafish.Jaclyn P Souder et al.Toxicological sciences : an official journal of the Society of Toxicology, 170(1), 25-44 (2019-03-26) Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin.Thomas K H Chang et al.Journal of pineal research, 48(1), 55-64 (2009-11-19) A comparison of in vitro ADME properties and pharmacokinetics of azithromycin and selected 15-membered ring macrolides in rodents.Astrid Milić et al.European journal of drug metabolism and pharmacokinetics, 39(4), 263-276 (2013-10-12) The aryl hydrocarbon receptor pathway and the response to 3-methylcholanthrene are altered in the liver of adrenalectomized rats.Anne K Mullen Grey et al.Drug metabolism and disposition: the biological fate of chemicals, 39(1), 83-91 (2010-10-01) In vivo indirect measurement of cytochrome P450-associated activities in freshwater gastropod molluscs.Beatrice Gagnaire et al.Environmental toxicology, 25(6), 545-553 (2009-06-16) A resorufin derivative as a fluorogenic indicator for cell viabilityIshiyama M, et al. Analytical Sciences, 15(10), 1025-1028 (1999) BFCOD activity in fish cell lines and zebrafish embryos and its modulation by chemical ligands of human aryl hydrocarbon and nuclear receptors.N Creusot et al.Environmental science and pollution research international, 22(21), 16393-16404 (2014-12-05) Up-regulation of cytochrome P450 and phase II enzyme systems in rat precision-cut rat lung slices by the intact glucosinolates, glucoraphanin and glucoerucin.Ahmad Faizal Abdull Razis et al.Lung cancer (Amsterdam, Netherlands), 71(3), 298-305 (2010-07-20) The licorice flavonoid isoliquiritigenin reduces DNA-binding activity of AhR in MCF-7 cells.Tsz Yan Wong et al.Chemico-biological interactions, 221, 70-76 (2014-08-12) Engineering bacterial cytochrome P450 (P450) BM3 into a prototype with human P450 enzyme activity using indigo formation.Sun-Ha Park et al.Drug metabolism and disposition: the biological fate of chemicals, 38(5), 732-739 (2010-01-27) Ethoxy-, pentoxy- and benzyloxyphenoxazones and homologues: a series of substrates to distinguish between different induced cytochromes P-450.M D Burke et al.Biochemical pharmacology, 34(18), 3337-3345 (1985-09-15) Mice deficient in the gene for cytochrome P450 (CYP)1A1 are more susceptible than wild-type to hyperoxic lung injury: evidence for protective role of CYP1A1 against oxidative stress.Krithika Lingappan et al.Toxicological sciences : an official journal of the Society of Toxicology, 141(1), 68-77 (2014-06-05) Disruption of cytochrome P4501A2 in mice leads to increased susceptibility to hyperoxic lung injury.Lihua Wang et al.Free radical biology & medicine, 82, 147-159 (2015-02-15) The naturally occurring aliphatic isothiocyanates sulforaphane and erucin are weak agonists but potent non-competitive antagonists of the aryl hydrocarbon receptor.Ahmad F Abdull Razis et al.Archives of toxicology, 86(10), 1505-1514 (2012-05-31) Tolbutamide hydroxylation by hepatic microsomes from Atlantic salmon (Salmo salar L.).AnnaLotta Schiller Vestergren et al.Molecular biology reports, 39(6), 6867-6873 (2012-02-09) Modulation of cytochrome P450 2A5 activity by lipopolysaccharide: low-dose effects and non-monotonic dose-response relationship.Ana C A X De-Oliveira et al.PloS one, 10(1), e0117842-e0117842 (2015-01-31) The point of transition on the dose-effect curve as a reference point in the evaluation of in vitro toxicity data.Salomon Sand et al.Journal of applied toxicology : JAT, 32(10), 843-849 (2012-06-27) Biotransformation and Oxidative Stress Responses in Captive Nile Crocodile (Crocodylus niloticus) Exposed to Organic Contaminants from the Natural Environment in South Africa.Augustine Arukwe et al.PloS one, 10(6), e0130002-e0130002 (2015-06-19) Assessment of biological effects of pollutants in a hyper eutrophic tropical water body, Lake Beira, Sri Lanka using multiple biomarker responses of resident fish, Nile tilapia (Oreochromis niloticus).Asoka Pathiratne et al.Ecotoxicology (London, England), 19(6), 1019-1026 (2010-03-17) HepG2 cells as an in vitro model for evaluation of cytochrome P450 induction by xenobiotics.Jong Min Choi et al.Archives of pharmacal research, 38(5), 691-704 (2014-10-23) Cancer preventive potential of methanol extracts of Hypsizigus marmoreus.Jong Sun Chang et al.Journal of medicinal food, 12(3), 493-500 (2009-07-25) Phenethyl isothiocyanate, a naturally occurring phytochemical, is an antagonist of the aryl hydrocarbon receptor.Ahmad F Abdull Razis et al.Molecular nutrition & food research, 56(3), 425-434 (2011-12-17) A methoxyflavonoid, chrysoeriol, selectively inhibits the formation of a carcinogenic estrogen metabolite in MCF-7 breast cancer cells.Hitomi Takemura et al.The Journal of steroid biochemistry and molecular biology, 118(1-2), 70-76 (2009-10-17) CYP1D1, pseudogenized in human, is expressed and encodes a functional drug-metabolizing enzyme in cynomolgus monkey.Yasuhiro Uno et al.Biochemical pharmacology, 81(3), 442-450 (2010-11-13) Effect of broccoli (Brassica oleracea) and its phytochemical sulforaphane in balanced diets on the detoxification enzymes levels of tilapia (Oreochromis niloticus) exposed to a carcinogenic and mutagenic pollutant.V Villa-Cruz et al.Chemosphere, 74(9), 1145-1151 (2009-01-16) Effect of commercially available green and black tea beverages on drug-metabolizing enzymes and oxidative stress in Wistar rats.Hsien-Tsung Yao et al.Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 70, 120-127 (2014-05-13)

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