cis-stilbene oxide
bibenzyl, alpha,alpha'-epoxy-, cis-
 
Notes:
None found
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CAS Number: 1689-71-0Picture of molecule3D/inchi
FDA UNII: GIX80CN6Z7
Nikkaji Web: J878H
Beilstein Number: 0082737
MDL: MFCD00005122
XlogP3: 2.90 (est)
Molecular Weight: 196.24884000
Formula: C14 H12 O
NMR Predictor: Predict (works with chrome or firefox)
Category: information only not used for fragrances or flavors
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Flash Point: > 230.00 °F. TCC ( > 110.00 °C. )
Soluble in:
 water, 80.82 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Sigma-Aldrich: Aldrich
For experimental / research use only.
cis-Stilbene Oxide 97%
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: information only not used for fragrances or flavors
Recommendation for cis-stilbene oxide usage levels up to:
 not for fragrance use.
 
Recommendation for cis-stilbene oxide flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System: Search
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 98511
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 (2R,3S)-2,3-diphenyloxirane
Chemidplus: 0001689710
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References:
 (2R,3S)-2,3-diphenyloxirane
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 98511
Pubchem (sid): 135056891
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
KEGG (GenomeNet): C16014
HMDB (The Human Metabolome Database): HMDBP01791
Export Tariff Code: 2910.90.2000
ChemSpider: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 not found in nature
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Synonyms:
 bibenzyl, alpha,alpha'-epoxy-, cis-
cis-2,3-diphenyl oxirane
(2R,3S)-2,3-diphenyloxirane
 oxirane, 2,3-diphenyl-, cis- (9CI)
(Z)-stilbene oxide
 stilbene oxide, cis-
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Articles:
PubMed: A novel activity of microsomal epoxide hydrolase: metabolism of the endocannabinoid 2-arachidonoylglycerol.
PubMed: Highly enantioselective iron(II)-catalyzed opening reaction of aromatic meso-epoxides with indoles.
PubMed: Characterization of Hovi-mEH1, a microsomal epoxide hydrolase from the glassy-winged sharpshooter Homalodisca vitripennis.
PubMed: Cloning and characterization of a microsomal epoxide hydrolase from Heliothis virescens.
PubMed: An electric field-induced change in the selectivity of a metal oxide-catalyzed epoxide rearrangement.
PubMed: Development of fluorescent substrates for microsomal epoxide hydrolase and application to inhibition studies.
PubMed: Modular, active, and robust Lewis acid catalysts supported on a metal-organic framework.
PubMed: Crystal structure of the cystic fibrosis transmembrane conductance regulator inhibitory factor Cif reveals novel active-site features of an epoxide hydrolase virulence factor.
PubMed: Regulation of JH epoxide hydrolase versus JH esterase activity in the cabbage looper, Trichoplusia ni, by juvenile hormone and xenobiotics.
PubMed: The Saccharomyces cerevisiae ORF YNR064c protein has characteristics of an 'orphaned' epoxide hydrolase.
PubMed: Parallel mechanistic studies on the counterion effect of manganese salen and porphyrin complexes on olefin epoxidation by iodosylarenes.
PubMed: Functional analysis of human microsomal epoxide hydrolase genetic variants.
PubMed: Epoxide hydrolases in the rat epididymis: possible roles in xenobiotic and endogenous fatty acid metabolism.
PubMed: Characterization and cDNA cloning of a clofibrate-inducible microsomal epoxide hydrolase in Drosophila melanogaster.
PubMed: Kinetics and mechanism of rhenium-catalyzed O atom transfer from epoxides.
PubMed: Non-synonymous single nucleotide alterations in the microsomal epoxide hydrolase gene and their functional effects.
PubMed: Brassica napus soluble epoxide hydrolase (BNSEH1).
PubMed: Overexpression of Arabidopsis thaliana soluble epoxide hydrolase 1 in Pichia pastoris and characterisation of the recombinant enzyme.
PubMed: Activation of nitrous oxide and selective epoxidation of alkenes catalyzed by the manganese-substituted polyoxometalate, [Mn(III)2ZnW(Zn2W9O34)2]10-.
PubMed: Expression and activity of microsomal epoxide hydrolase in follicles isolated from mouse ovaries.
PubMed: Comparative metabolism and excretion of benzo(a)pyrene in 2 species of ictalurid catfish.
PubMed: First success of catalytic epoxidation of olefins by an electron-rich iron(III) porphyrin complex and H2O2: imidazole effect on the activation of H2O2 by iron porphyrin complexes in aprotic solvent.
PubMed: Metabolic activation of the proestrogens trans-stilbene and trans-stilbene oxide by rat liver microsomes.
PubMed: Cress and potato soluble epoxide hydrolases: purification, biochemical characterization, and comparison to mammalian enzymes.
PubMed: Reduction of stilbene oxide and styrene oxide to the corresponding alkenes by intestinal bacteria.
PubMed: Biochemical evidence for the involvement of tyrosine in epoxide activation during the catalytic cycle of epoxide hydrolase.
PubMed: Epoxide hydrolase--polymorphism and role in toxicology.
PubMed: Induction of hepatic heme oxygenase and changes in cytochrome P-450s in response to oxidative stress produced by stilbenes and stilbene oxides in rats.
PubMed: Characterization of epoxide hydrolase activity in Alternaria alternata f. sp. lycopersici. Possible involvement in toxin production.
PubMed: Assessment of possible protective roles of selenium, zinc, and cis-stilbene oxide against acute T-2 toxin poisoning: a preliminary report.
PubMed: Selective Oxygen Transfers with Iron(III) Porphyrin Nitrite.
PubMed: Interindividual and interspecies variation in hepatic microsomal epoxide hydrolase activity: studies with cis-stilbene oxide, carbamazepine 10, 11-epoxide and naphthalene.
PubMed: Development of an in situ toxicity assay system using recombinant baculoviruses.
PubMed: Kinetic parameters of lymphocyte microsomal epoxide hydrolase in carbamazepine hypersensitive patients. Assessment by radiometric HPLC.
PubMed: Induction of metallothionein synthesis by glutathione depletion after trans- and cis-stilbene oxide administration in rats.
PubMed: Lymphocyte microsomal epoxide hydrolase in patients on carbamazepine therapy.
PubMed: Kinetics and stereochemistry of the microsomal epoxide hydrolase-catalyzed hydrolysis of cis-stilbene oxides.
PubMed: Selective induction of rat liver phase II enzymes by N-heterocycle analogues of phenanthrene: a response exhibiting high correlation between UDP-glucuronosyltransferase and microsomal epoxide hydrolase activities.
PubMed: Effects of environmentally encountered epoxides on mouse liver epoxide-metabolizing enzymes.
PubMed: Comparative studies of the effects of stilbene compounds on hepatic ornithine decarboxylase and S-adenosylmethionine decarboxylase induction in rats.
PubMed: Expression of arylhydrocarbon hydroxylase, epoxide hydrolases, glutathione S-transferase and UDP-glucuronosyltransferases in H5-6 hepatoma cells.
PubMed: Rat and human liver cytosolic epoxide hydrolases: evidence for multiple forms at level of protein and mRNA.
PubMed: Human glutathione S-transferase deficiency as a marker of susceptibility to epoxide-induced cytogenetic damage.
PubMed: Characterization of distinct forms of cytochromes P-450, epoxide metabolizing enzymes and UDP-glucuronosyltransferases in rat skin.
PubMed: Effect of hypolipidemic compounds on lauric acid hydroxylation and phase II enzymes.
PubMed: Microsomal and cytosolic epoxide hydrolase and glutathione S-transferase activities in the gill, liver, and kidney of the rainbow trout, Salmo gairdneri. Baseline levels and optimization of assay conditions.
PubMed: The low reactivity of 5H-dibenzo[a, d]cycloheptene 10,11-oxide in microsomal epoxide hydrolase catalysed hydration.
PubMed: Immunochemical comparison of human and rhesus monkey liver microsomal and the hepatocellular carcinoma-induced human serum epoxide hydrolases (preneoplastic antigens): basis for an enzyme-linked immunoabsorbent assay.
PubMed: Human liver cytosolic epoxide hydrolases.
PubMed: Hepatic epoxide hydrolase activities and their induction by clofibrate and diethylhexylphthalate in various strains of mice.
PubMed: Metabolism of tridiphane (2-(3,5-dichlorophenyl)-2(2,2,2-trichloroethyl)oxirane) by hepatic epoxide hydrolases and glutathione S-transferases in mouse.
PubMed: Purification of microsomal epoxide hydrolase from liver of rhesus monkey: partial separation of cis- and trans-stilbene oxide hydrolase.
PubMed: The effect of tridiphane (2-(3,5-dichlorophenyl)-2-(2,2,2-trichloroethyl)oxirane) on hepatic epoxide-metabolizing enzymes: indications of peroxisome proliferation.
PubMed: Inhibition of epoxide hydrolases and glutathione S-transferases by 2-, 3-, and 4-substituted derivatives of 4'-phenylchalcone and its oxide.
PubMed: Stereoselectivity and enantioselectivity of glutathione S-transferase toward stilbene oxide substrates.
PubMed: Hepatic levels of cytosolic, microsomal and 'mitochondrial' epoxide hydrolases and other drug-metabolizing enzymes after treatment of mice with various xenobiotics and endogenous compounds.
PubMed: Subcellular and organ distribution of cholesterol epoxide hydrolase in the rat.
PubMed: Epoxide hydrolysis in the cytosol of rat liver, kidney, and testis. Measurement in the presence of glutathione and the effect of dietary clofibrate.
PubMed: Effect of aging on testicular epoxide hydrolase and glutathione-S-transferase activities in mice.
PubMed: Comparison of crude and affinity purified cytosolic epoxide hydrolases from hepatic tissue of control and clofibrate-fed mice.
PubMed: Subcellular distribution, catalytic properties and partial purification of epoxide hydrolase in the human adrenal gland.
PubMed: Hereditary interindividual differences in the glutathione transferase activity towards trans-stilbene oxide in resting human mononuclear leukocytes are due to a particular isozyme(s).
PubMed: Properties of cytosolic epoxide hydrolase purified from the liver of untreated and clofibrate-treated mice. Characterization of optimal assay conditions, substrate specificity and effects of modulators on the catalytic activity.
PubMed: Effect of dietary clofibrate on epoxide hydrolase activity in tissues of mice.
PubMed: Epoxide metabolism in the liver of mice treated with clofibrate (ethyl-alpha-(p-chlorophenoxyisobutyrate)), a peroxisome proliferator.
PubMed: Cyclopropyl oxiranes: reversible inhibitors of cytosolic and microsomal epoxide hydrolases.
PubMed: A methodology for the analysis of the preneoplastic antigen.
PubMed: Measurement and characterization of membrane-bound and soluble epoxide hydrolase activities in resting mononuclear leukocytes from human blood.
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