3,4-EPOXY-1-BUTENE

Details

Stereochemistry	RACEMIC
Molecular Formula	C4H6O
Molecular Weight	70.0898
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C=CC1CO1

InChI

InChIKey=GXBYFVGCMPJVJX-UHFFFAOYSA-N

InChI=1S/C4H6O/c1-2-4-3-5-4/h2,4H,1,3H2

HIDE SMILES / InChI

Molecular Formula	C4H6O
Molecular Weight	70.0898
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Approval Year

PubMed

Title	Date	PubMed
Inhibitory potency of 4-carbon alkanes and alkenes toward CYP2E1 activity.	2014-04-06	24561005
1,3-Butadiene: II. Genotoxicity profile.	2010-10	20868267
Mutagenicity of stereochemical configurations of 1,3-butadiene epoxy metabolites in human cells.	2010-06	20853577
Exposure-response of 1,2:3,4-diepoxybutane-specific N-terminal valine adducts in mice and rats after inhalation exposure to 1,3-butadiene.	2010-06	20176624
Quantitative investigation on the metabolism of 1,3-butadiene and of its oxidized metabolites in once-through perfused livers of mice and rats.	2010-03	20007191
Stereoselective ring expansion of vinyl oxiranes: mechanistic insights and natural product total synthesis.	2010-02-22	20135664
Cob(I)alamin for trapping butadiene epoxides in metabolism with rat S9 and for determining associated kinetic parameters.	2009-09	19764821
Genotoxicity of 1,3-butadiene and its epoxy intermediates.	2009-08	20017413
Investigation on the mechanisms of genotoxicity of butadiene, styrene and their combination in human lymphocytes using the Comet assay.	2009-05-12	19428383
An efficient and general enantioselective synthesis of sphingosine, phythosphingosine, and 4-substituted derivatives.	2009-01-01	19053731
Evaluation of cancer tests of 1,3-butadiene using internal dose, genotoxic potency, and a multiplicative risk model.	2008-10-01	18829559
Bimetallic dendrimer-encapsulated nanoparticles as catalysts: a review of the research advances.	2008-08	18648686
HPRT mutations in lymphocytes from 1,3-butadiene-exposed workers in China.	2008-02	18288319
Catalytic performance of symmetrical and unsymmetrical sulfur-containing pincer complexes: synthesis and tandem catalytic activity of the first PCS-pincer palladium complex.	2008	18432627
Development of a physiologically based toxicokinetic model for butadiene and four major metabolites in humans: global sensitivity analysis for experimental design issues.	2007-05-01	17397815
Identification of covalent modifications in P450 2E1 by 1,2-epoxy-3-butene in vitro.	2007-03-20	17298833
N-terminal globin adducts as biomarkers for formation of butadiene derived epoxides.	2007-03-20	17084829
Quantitative analysis of N-terminal valine peptide adducts specific for 1,2-epoxy-3-butene.	2007-03-20	16860298
Mutagenicity of stereochemical configurations of 1,2-epoxybutene and 1,2:3,4-diepoxybutane in human lymphblastoid cells.	2007-03-20	16854403
Synthesis of DNA oligodeoxynucleotides containing structurally defined N6-(2-hydroxy-3-buten-1-yl)-adenine adducts of 3,4-epoxy-1-butene.	2007-03-20	16765925
Some insights into the mode of action of butadiene by examining the genotoxicity of its metabolites.	2007-03-20	16698003
Metabolism of 1,3-butadiene to toxicologically relevant metabolites in single-exposed mice and rats.	2007-03-20	16616907
Copper-catalyzed rearrangement of vinyl oxiranes.	2006-12-20	17165756
Palladium-catalyzed DYKAT of butadiene monoepoxide: enantioselective total synthesis of (+)-DMDP, (-)-bulgecinine, and (+)-broussonetine G.	2006-08-25	16807949
Cellular analysis of disorazole C and structure-activity relationship of analogs of the natural product.	2006-01	16492150
3,4-Epoxy-1-butene, a reactive metabolite of 1,3-butadiene, induces somatic mutations in Xpc-null mice.	2006-01	16094661
Hemoglobin adducts and micronuclei in rodents after treatment with isoprene monoxide or butadiene monoxide.	2005-08-01	15925539
Structure of an oligodeoxynucleotide containing a butadiene oxide-derived N1 beta-hydroxyalkyl deoxyinosine adduct in the human N-ras codon 61 sequence.	2005-03-08	15736943
Regio- and stereoselectivity of the addition of O-, S-, N-, and C-nucleophiles to the beta vinyl oxirane derived from D-glucal.	2004-12-10	15575746
Effects of 1,3-butadiene, isoprene, and their photochemical degradation products on human lung cells.	2004-11	15531432
Synthesis of chiral phosphoantigens and their activity in gamma delta T cell stimulation.	2004-09-06	15357974
DNA adducts in rats and mice following exposure to [4-14C]-1,2-epoxy-3-butene and to [2,3-14C]-1,3-butadiene.	2004-06-30	15223358
Characterization of alkyl-cobalamins formed on trapping of epoxide metabolites of 1,3-butadiene.	2004-05	15335048
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.	2004-03-15	15013822
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.	2004-03-15	15013821
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.	2003-12	14680375
Genetic susceptibility, biomarker respones, and cancer.	2003-11	14644336
Mutagenic spectrum of butadiene-derived N1-deoxyinosine adducts and N6,N6-deoxyadenosine intrastrand cross-links in mammalian cells.	2002-12	12482239
New stereoselective beta-glycosylation via a vinyl oxirane derived from D-glucal.	2002-10-17	12375921
Synthesis and characterization of water-soluble hydroxybutenyl cyclomaltooligosaccharides (cyclodextrins).	2002-03-15	11890887
Enantioselective allylation of beta,gamma-unsaturated aldehydes generated via Lewis acid induced rearrangement of 2-vinyloxiranes.	2002-01-10	11772096
Dose-dependent excretion of unconjugated 3-butene-1,2-diol measured in urine with a gc/ms after 1,3-butadiene exposure.	2002	20021174
In vitro genotoxicity testing of (1-chloroethenyl)oxirane, a metabolite of beta-chloroprene.	2001-06-01	11397425
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.	2001-06-01	11397423
Advances in the mass spectrometry of hemoglobin adducts: global analysis of the covalent binding of butadiene monoxide.	2001-06-01	11397420
Mutational spectrum of 1,3-butadiene and metabolites 1,2-epoxybutene and 1,2,3,4-diepoxybutane to assess mutagenic mechanisms.	2001-06-01	11397399
Development of a preliminary physiologically based toxicokinetic (PBTK) model for 1,3-butadiene risk assessment.	2001-06-01	11397398
Synthesis and characterization of oligodeoxynucleotides containing an N1 beta-hydroxyalkyl adduct of 2'-deoxyinosine.	2001-06	11409946
Point mutations induced by 1,2-epoxy-3-butene N1 deoxyinosine adducts.	2001	11774359
Reactive metabolites of 1,3-butadiene: DNA and hemoglobin adduct formation and potential roles in carcinogenicity.	2001	11765021

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:11:48 GMT 2025` Edited by `admin` on `Mon Mar 31 22:11:48 GMT 2025`
Record UNII	478ERR5NKR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

3,4-EPOXY-1-BUTENE

Systematic Name

English

NSC-24251

Preferred Name

English

OXIRANE, 2-ETHENYL-

Systematic Name

English

3,4-EPOXY-1-BUTENE [HSDB]

Common Name

English

OXIRANE, ETHENYL-

Systematic Name

English

VINYL EPOXIDE

Common Name

English

NSC-8023

Code

English

EPOXYBUTADIENE

Systematic Name

English

1,3-BUTADIENE MONOEPOXIDE

Common Name

English

VINYLOXIRANE

Systematic Name

English

(±)-VINYLOXIRANE

Systematic Name

English

2-VINYLOXIRANE

Systematic Name

English

1,2-OXIDO-3-BUTENE

Common Name

English

1,2-EPOXY-3-BUTENE

Systematic Name

English

1-BUTENE, 3,4-EPOXY-

Systematic Name

English

BUTADIENE EPOXIDE

Common Name

English

BUTADIENE MONOXIDE

Systematic Name

English

1,3-BUTADIENE MONOOXIDE

Systematic Name

English

Code System Code Type Description

PUBCHEM

13586