1,3-Butadiene (T3D0156)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (2)XML
Targets (2)
Record Information
Version2.0
Creation Date2009-03-06 18:58:11 UTC
Update Date2014-12-24 20:21:14 UTC
Accession NumberT3D0156
Identification
Common Name1,3-Butadiene
ClassSmall Molecule
Description1,3-Butadiene is a simple conjugated diene with the formula C4H6. It is an important industrial chemical used as a monomer in the production of synthetic rubber. When the word butadiene is used, most of the time it refers to 1,3-butadiene. 1,3-Butadiene is inconvenient for laboratory use because it is a flammable gas subject to polymerization on storage. 3-Butadiene cyclic sulfone (sulfolene) is a convenient solid storable source for 1,3-butadiene for many laboratory purposes when the generation of sulfur dioxide byproduct in the reaction mixture is not objectionable. Long-term exposure has been associated with cardiovascular disease, there is a consistent association with leukemia, and weaker association with other cancers. Most butadiene is polymerized to produce synthetic rubber. While polybutadiene itself is a very soft, almost liquid material, copolymers prepared from mixtures of butadiene with styrene and/or acrylonitrile, such as acrylonitrile butadiene styrene (ABS), acrylonitrile butadiene (NBR) and styrene-butadiene (SBR) are tough and elastic. SBR is the material most commonly used for the production of automobile tires. Smaller amounts of butadiene are used to make the nylon intermediate, adiponitrile, by the addition of a molecule of hydrogen cyanide to each of the double bonds in a process called hydrocyanation developed by DuPont. Other synthetic rubber materials such as chloroprene, and the solvent sulfolane are also manufactured from butadiene. Butadiene is used in the industrial production of 4-vinylcyclohexene via a Diels Alder dimerization reaction and the vinylcyclohexene is a common impurity found in butadiene upon storage. Cyclooctadiene and cyclododecatriene are produced via nickel- or titanium-catalyzed dimerization and trimerization reactions, respectively. Butadiene is also useful in the synthesis of cycloalkanes and cycloalkenes, as it reacts with double and triple carbon-carbon bonds through the Diels-Alder reaction. The name butadiene can also refer to the isomer, 1,2-butadiene, which is a cumulated diene. However, this allene is difficult to prepare and has no industrial significance. This diene is also not expected to act as a diene in a Diels-Alder reaction due to its structure. To effect a Diels-Alder reaction only a conjugated diene will suffice.
Compound Type
  • Cigarette Toxin
  • Household Toxin
  • Industrial Precursor/Intermediate
  • Industrial/Workplace Toxin
  • Lachrymator
  • Metabolite
  • Organic Compound
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
1,3-Butadien
alpha,gamma-Butadiene
alpha,«gamma»-Butadiene
Biethylene
Bivinyl
Buta-1,3-dieen
Buta-1,3-dien
Buta-1,3-diene
Butadieen
Butadien
Butadiene
CH22CH1CH2CH2
CH2=CHCH=CH2
Divinyl
Erythrene
Pyrrolylene
Vinylethylene
Chemical FormulaC4H6
Average Molecular Mass54.090 g/mol
Monoisotopic Mass54.047 g/mol
CAS Registry Number106-99-0
IUPAC Namebuta-1,3-diene
Traditional Name1,3-butadiene
SMILESC=CC=C
InChI IdentifierInChI=1S/C4H6/c1-3-4-2/h3-4H,1-2H2
InChI KeyInChIKey=KAKZBPTYRLMSJV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alkadienes. These are acyclic hydrocarbons that contain exactly two carbon-to-carbon double bonds.
KingdomOrganic compounds
Super ClassHydrocarbons
ClassUnsaturated hydrocarbons
Sub ClassOlefins
Direct ParentAlkadienes
Alternative Parents
Substituents
  • Alkadiene
  • Unsaturated aliphatic hydrocarbon
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless gas.
Experimental Properties
PropertyValue
Melting Point-108.9°C
Boiling PointNot Available
Solubility0.735 mg/mL at 25°C
LogP1.99
Predicted Properties
PropertyValueSource
Water Solubility0.98 g/LALOGPS
logP1.94ALOGPS
logP1.63ChemAxon
logS-1.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.29 m³·mol⁻¹ChemAxon
Polarizability6.7 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ufr-9000000000-cddbfceffd529008d5ec2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ufr-9000000000-cddbfceffd529008d5ec2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-9000000000-e4f51ef2fbf933007d392017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-805abc61b7c8de6c57892016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-805abc61b7c8de6c57892016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-46aa55de9e12fa462b492016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-9000000000-191296d0bc49a4a79c022016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-9000000000-191296d0bc49a4a79c022016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-9000000000-7031b766ca514dc531b42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-9000000000-0d737e29499be79402072021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-9000000000-0d737e29499be79402072021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-9000000000-0d737e29499be79402072021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-1924391f943e092b44862021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-c60974066ebc2547dd572021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-9000000000-45337fddf4aab37b4ba02021-09-22View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-9000000000-cfc5558b93570d1d78c02014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CCl4, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
Toxicity Profile
Route of ExposureInhalation (8)
Mechanism of ToxicityCertain metabolites of 1,3-butadiene have been shown to bind to DNA and nucleoproteins, forming protein-DNA and DNA-DNA crosslinks. Specifically, 1,2-epoxybutene-3 and diepoxybutane react with guanine to cause crosslinking. (8, 1)
Metabolism1,3-Butadiene is absorbed following inhalation and is distributed to the adipose tissue, brain, liver, septum, and kidney. 1,3-Butadiene is believed to be metabolized in the liver by cytochrome P-450 enzymes, forming 1,2-epoxybutene-3 as the main metabolite. 1,2-Epoxybutene-3 is further transformed into 3-butene-1,2-diol by microsomal epoxide hydrolase. The metabolites of 1,3-butadiene are exhaled as carbon dioxide or excreted in the urine. (8)
Toxicity ValuesLD50: 3.21 g/kg (Oral, Mouse) (4) LC50: 270 000 mg/m3 over 2 hours (Inhalation, Mouse) (4)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)1, carcinogenic to humans. (7)
Uses/Sources1,3-Butadiene is made from the processing of petroleum. It is used mainly to make synthetic rubber for tires. It is also used to make plastics such as acrylics, and small amounts can be found in gasoline. (8)
Minimum Risk LevelNot Available
Health EffectsBreathing high levels of 1,3-butadiene causes central nervous system damage. Chronic exposure may also cause lung damage and kidney, liver, and cardiovascular disease. In addition, 1,3-butadiene is a known human carcinogen. (8)
SymptomsBreathing 1,3-butadiene may cause irritation of the eyes, nose, and throat. High levels of 1,3-butadiene can also cause, blurred vision, nausea, fatigue, headache, decreased blood pressure and pulse rate, and unconsciousness. Skin contact with liquid 1,3-butadiene can cause irritation and frostbite. (8)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB41792
PubChem Compound ID7845
ChEMBL IDCHEMBL537970
ChemSpider ID7557
KEGG IDC16450
UniProt IDNot Available
OMIM ID
ChEBI ID39478
BioCyc IDBUTADIENE
CTD IDC031763
Stitch ID1,3-Butadiene
PDB IDNot Available
ACToR ID204
Wikipedia Link1,3-butadiene
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Goggin M, Loeber R, Park S, Walker V, Wickliffe J, Tretyakova N: HPLC-ESI+-MS/MS analysis of N7-guanine-N7-guanine DNA cross-links in tissues of mice exposed to 1,3-butadiene. Chem Res Toxicol. 2007 May;20(5):839-47. Epub 2007 Apr 25. [17455958 ]
  2. Boysen G, Scarlett CO, Temple B, Combs TP, Brooks NL, Borchers CH, Swenberg JA: Identification of covalent modifications in P450 2E1 by 1,2-epoxy-3-butene in vitro. Chem Biol Interact. 2007 Mar 20;166(1-3):170-5. Epub 2007 Jan 17. [17298833 ]
  3. Norppa H: Genetic susceptibility, biomarker respones, and cancer. Mutat Res. 2003 Nov;544(2-3):339-48. [14644336 ]
  4. Ollagnier-de Choudens S, Fontecave M: The lipoate synthase from Escherichia coli is an iron-sulfur protein. FEBS Lett. 1999 Jun 18;453(1-2):25-8. [10403368 ]
  5. Zhang ZC, Zhang X, Yu QY, Liu ZC, Xu CM, Gao JS, Zhuang J, Wang X: Pd cluster nanowires as highly efficient catalysts for selective hydrogenation reactions. Chemistry. 2012 Feb 27;18(9):2639-45. doi: 10.1002/chem.201102903. Epub 2012 Jan 26. [22282407 ]
  6. USEPA (1985). Health Assessment Document: 1,3-Butadiene. EPA-600/8-85-004A.
  7. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  8. ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological Profile for 1,3-butadiene . U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Transient receptor potential cation channel subfamily A member 1
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Deering-Rice CE, Romero EG, Shapiro D, Hughen RW, Light AR, Yost GS, Veranth JM, Reilly CA: Electrophilic components of diesel exhaust particles (DEP) activate transient receptor potential ankyrin-1 (TRPA1): a probable mechanism of acute pulmonary toxicity for DEP. Chem Res Toxicol. 2011 Jun 20;24(6):950-9. doi: 10.1021/tx200123z. Epub 2011 May 25. [21591660 ]
  2. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]
2. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological Profile for 1,3-butadiene . U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]