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Butadiene monoxide

CAS No.:
930-22-3
Catalog Number:
AG0033IV
Molecular Formula:
C4H6O
Molecular Weight:
70.0898
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1g
97%
In Stock USA
United States
$50
- +
5g
97%
In Stock USA
United States
$150
- +
10g
97%
In Stock USA
United States
$263
- +
25g
97%
In Stock USA
United States
$525
- +
100g
97%
In Stock USA
United States
$1500
- +
Product Description
Catalog Number:
AG0033IV
Chemical Name:
Butadiene monoxide
CAS Number:
930-22-3
Molecular Formula:
C4H6O
Molecular Weight:
70.0898
MDL Number:
MFCD00005149
IUPAC Name:
2-ethenyloxirane
InChI:
InChI=1S/C4H6O/c1-2-4-3-5-4/h2,4H,1,3H2
InChI Key:
GXBYFVGCMPJVJX-UHFFFAOYSA-N
SMILES:
C=CC1CO1
EC Number:
213-210-4
UN Number:
1993
Properties
Complexity:
49.6  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
70.042g/mol
Formal Charge:
0
Heavy Atom Count:
5  
Hydrogen Bond Acceptor Count:
1  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
70.091g/mol
Monoisotopic Mass:
70.042g/mol
Rotatable Bond Count:
1  
Topological Polar Surface Area:
12.5A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0
XLogP3:
0.5  
Literature
Title Journal
Inhibitory potency of 4-carbon alkanes and alkenes toward CYP2E1 activity. Toxicology 20140406
DNA damage induced by three major metabolites of 1,3-butadiene in human hepatocyte L02 cells. Mutation research 20120918
A mechanistic modeling framework for predicting metabolic interactions in complex mixtures. Environmental health perspectives 20111201
Kinetics of ethylene and ethylene oxide in subcellular fractions of lungs and livers of male B6C3F1 mice and male fischer 344 rats and of human livers. Toxicological sciences : an official journal of the Society of Toxicology 20111001
Quantitative analysis of trihydroxybutyl mercapturic acid, a urinary metabolite of 1,3-butadiene, in humans. Chemical research in toxicology 20110919
1,3-Butadiene: Biomarkers and application to risk assessment. Chemico-biological interactions 20110630
Stereoselective coupling reaction of dimethylzinc and alkyne toward nickelacycles. Organic letters 20110506
1,3-Butadiene: II. Genotoxicity profile. Critical reviews in toxicology 20101001
Exposure-response of 1,2:3,4-diepoxybutane-specific N-terminal valine adducts in mice and rats after inhalation exposure to 1,3-butadiene. Toxicological sciences : an official journal of the Society of Toxicology 20100601
Mutagenicity of stereochemical configurations of 1,3-butadiene epoxy metabolites in human cells. Research report (Health Effects Institute) 20100601
Quantitative investigation on the metabolism of 1,3-butadiene and of its oxidized metabolites in once-through perfused livers of mice and rats. Toxicological sciences : an official journal of the Society of Toxicology 20100301
Stereoselective ring expansion of vinyl oxiranes: mechanistic insights and natural product total synthesis. Angewandte Chemie (International ed. in English) 20100222
Cob(I)alamin for trapping butadiene epoxides in metabolism with rat S9 and for determining associated kinetic parameters. Chemical research in toxicology 20090901
Genotoxicity of 1,3-butadiene and its epoxy intermediates. Research report (Health Effects Institute) 20090801
Investigation on the mechanisms of genotoxicity of butadiene, styrene and their combination in human lymphocytes using the Comet assay. Mutation research 20090512
Alternative reagents for chemical noise reduction in liquid chromatography-mass spectrometry using selective ion-molecule reactions. Journal of the American Society for Mass Spectrometry 20090101
An efficient and general enantioselective synthesis of sphingosine, phythosphingosine, and 4-substituted derivatives. Organic letters 20090101
Evaluation of cancer tests of 1,3-butadiene using internal dose, genotoxic potency, and a multiplicative risk model. Cancer research 20081001
Bimetallic dendrimer-encapsulated nanoparticles as catalysts: a review of the research advances. Chemical Society reviews 20080801
HPRT mutations in lymphocytes from 1,3-butadiene-exposed workers in China. Environmental health perspectives 20080201
Catalytic performance of symmetrical and unsymmetrical sulfur-containing pincer complexes: synthesis and tandem catalytic activity of the first PCS-pincer palladium complex. Chemistry (Weinheim an der Bergstrasse, Germany) 20080101
Development of a physiologically based toxicokinetic model for butadiene and four major metabolites in humans: global sensitivity analysis for experimental design issues. Chemico-biological interactions 20070501
Metabolism of 1,3-butadiene to toxicologically relevant metabolites in single-exposed mice and rats. Chemico-biological interactions 20070320
Some insights into the mode of action of butadiene by examining the genotoxicity of its metabolites. Chemico-biological interactions 20070320
Synthesis of DNA oligodeoxynucleotides containing structurally defined N6-(2-hydroxy-3-buten-1-yl)-adenine adducts of 3,4-epoxy-1-butene. Chemico-biological interactions 20070320
Mutagenicity of stereochemical configurations of 1,2-epoxybutene and 1,2:3,4-diepoxybutane in human lymphblastoid cells. Chemico-biological interactions 20070320
Quantitative analysis of N-terminal valine peptide adducts specific for 1,2-epoxy-3-butene. Chemico-biological interactions 20070320
N-terminal globin adducts as biomarkers for formation of butadiene derived epoxides. Chemico-biological interactions 20070320
Identification of covalent modifications in P450 2E1 by 1,2-epoxy-3-butene in vitro. Chemico-biological interactions 20070320
Copper-catalyzed rearrangement of vinyl oxiranes. Journal of the American Chemical Society 20061220
Palladium-catalyzed DYKAT of butadiene monoepoxide: enantioselective total synthesis of (+)-DMDP, (-)-bulgecinine, and (+)-broussonetine G. Chemistry (Weinheim an der Bergstrasse, Germany) 20060825
3,4-Epoxy-1-butene, a reactive metabolite of 1,3-butadiene, induces somatic mutations in Xpc-null mice. Environmental and molecular mutagenesis 20060101
Cellular analysis of disorazole C and structure-activity relationship of analogs of the natural product. Chemical biology & drug design 20060101
Hemoglobin adducts and micronuclei in rodents after treatment with isoprene monoxide or butadiene monoxide. Mutation research 20050801
Structure of an oligodeoxynucleotide containing a butadiene oxide-derived N1 beta-hydroxyalkyl deoxyinosine adduct in the human N-ras codon 61 sequence. Biochemistry 20050308
Regio- and stereoselectivity of the addition of O-, S-, N-, and C-nucleophiles to the beta vinyl oxirane derived from D-glucal. The Journal of organic chemistry 20041210
Effects of 1,3-butadiene, isoprene, and their photochemical degradation products on human lung cells. Environmental health perspectives 20041101
Stereospecific uncatalyzed alpha-O-glycosylation and alpha-C-glycosidation by means of a new D-Gulal-derived alpha vinyl oxirane. The Journal of organic chemistry 20041015
Synthesis of chiral phosphoantigens and their activity in gamma delta T cell stimulation. Bioorganic & medicinal chemistry letters 20040906
DNA adducts in rats and mice following exposure to [4-14C]-1,2-epoxy-3-butene and to [2,3-14C]-1,3-butadiene. Chemico-biological interactions 20040630
Characterization of alkyl-cobalamins formed on trapping of epoxide metabolites of 1,3-butadiene. Journal of separation science 20040501
Dose responses for DNA adduct formation in tissues of rats and mice exposed by inhalation to low concentrations of 1,3-[2,3-[(14)C]-butadiene. Chemico-biological interactions 20040315
Dose responses for the formation of hemoglobin adducts and urinary metabolites in rats and mice exposed by inhalation to low concentrations of 1,3-[2,3-(14)C]-butadiene. Chemico-biological interactions 20040315
Identification and characterization of a series of nucleoside adducts formed by the reaction of 2'-deoxyguanosine and 1,2,3,4-diepoxybutane under physiological conditions. Chemical research in toxicology 20031201
Genetic susceptibility, biomarker respones, and cancer. Mutation research 20031101
Mutagenic spectrum of butadiene-derived N1-deoxyinosine adducts and N6,N6-deoxyadenosine intrastrand cross-links in mammalian cells. Chemical research in toxicology 20021201
New stereoselective beta-glycosylation via a vinyl oxirane derived from D-glucal. Organic letters 20021017
Synthesis and characterization of water-soluble hydroxybutenyl cyclomaltooligosaccharides (cyclodextrins). Carbohydrate research 20020315
Enantioselective allylation of beta,gamma-unsaturated aldehydes generated via Lewis acid induced rearrangement of 2-vinyloxiranes. Organic letters 20020110
Dose-dependent excretion of unconjugated 3-butene-1,2-diol measured in urine with a gc/ms after 1,3-butadiene exposure. Toxicology mechanisms and methods 20020101
Metabolism of butadiene monoxide by freshly isolated hepatocytes from mice and rats: different partitioning between oxidative, hydrolytic, and conjugation pathways. Drug metabolism and disposition: the biological fate of chemicals 20010601
Cellular and molecular basis for species, sex and tissue differences in 1,3-butadiene metabolism. Chemico-biological interactions 20010601
First-pass metabolism of 1,3-butadiene in once-through perfused livers of rats and mice. Chemico-biological interactions 20010601
Physiological modeling of butadiene disposition in mice and rats. Chemico-biological interactions 20010601
Development of a preliminary physiologically based toxicokinetic (PBTK) model for 1,3-butadiene risk assessment. Chemico-biological interactions 20010601
Mutational spectrum of 1,3-butadiene and metabolites 1,2-epoxybutene and 1,2,3,4-diepoxybutane to assess mutagenic mechanisms. Chemico-biological interactions 20010601
Advances in the mass spectrometry of hemoglobin adducts: global analysis of the covalent binding of butadiene monoxide. Chemico-biological interactions 20010601
A novel DNA adduct, originating from 1,2-epoxy-3,4-butanediol, is the major DNA adduct after exposure to [2,3-(14)C]-1,3-butadiene,[4-(14)C]-1,2-epoxy-3-butane. Chemico-biological interactions 20010601
In vitro genotoxicity testing of (1-chloroethenyl)oxirane, a metabolite of beta-chloroprene. Chemico-biological interactions 20010601
Synthesis and characterization of oligodeoxynucleotides containing an N1 beta-hydroxyalkyl adduct of 2'-deoxyinosine. Chemical research in toxicology 20010601
Synthesis and characterization of nucleosides and oligonucleotides bearing adducts of butadiene epoxides on adenine n(6) and guanine n(2). Chemical research in toxicology 20010401
Lung-specific mutagenicity and mutational spectrum in B6C3F1 lacI transgenic mice following inhalation exposure to 1,2-epoxybutene. Mutation research 20010125
Hemoglobin adducts of epoxybutene in workers occupationally exposed to 1,3-butadiene. Archives of toxicology 20010101
Reactive metabolites of 1,3-butadiene: DNA and hemoglobin adduct formation and potential roles in carcinogenicity. Advances in experimental medicine and biology 20010101
Point mutations induced by 1,2-epoxy-3-butene N1 deoxyinosine adducts. Environmental and molecular mutagenesis 20010101
1,3-Butadiene oxidation by human myeloperoxidase. Role of chloride ion in catalysis of divergent pathways. The Journal of biological chemistry 19921005
Properties