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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:39:41 UTC

Update Date

2022-03-07 02:57:12 UTC

HMDB ID

HMDB0041792

Secondary Accession Numbers

HMDB41792

Metabolite Identification

Common Name

1,3-Butadiene

Description

1,3-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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,3-Butadien	ChEBI
alpha,gamma-Butadiene	ChEBI
Bivinyl	ChEBI
Buta-1,3-dien	ChEBI
CH2=ch-CH=ch2	ChEBI
Divinyl	ChEBI
Vinylethylene	ChEBI
a,g-Butadiene	Generator
Α,γ-butadiene	Generator
alpha,«gamma»-butadiene	HMDB
Biethylene	HMDB
Buta-1,3-dieen	HMDB
Buta-1,3-diene	HMDB
Butadieen	HMDB
Butadien	HMDB
Butadiene	HMDB
CH22CH1CH2CH2	HMDB
CH2=chch=ch2	HMDB
Erythrene	HMDB
Pyrrolylene	HMDB
1,3-Butadiene	ChEBI

Chemical Formula

C₄H₆

Average Molecular Weight

54.0904

Monoisotopic Molecular Weight

54.046950192

IUPAC Name

buta-1,3-diene

Traditional Name

1,3-butadiene

CAS Registry Number

106-99-0

SMILES

C=CC=C

InChI Identifier

InChI=1S/C4H6/c1-3-4-2/h3-4H,1-2H2

InChI Key

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.

Kingdom

Organic compounds

Super Class

Hydrocarbons

Class

Unsaturated hydrocarbons

Sub Class

Olefins

Direct Parent

Alkadienes

Alternative Parents

Unsaturated aliphatic hydrocarbons

Substituents

Alkadiene
Unsaturated aliphatic hydrocarbon
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

butadiene (CHEBI:39478 )
a small molecule (BUTADIENE )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0041792)
Extracellular (HMDB: HMDB0041792)

Source

Exogenous

Exogenous (HMDB: HMDB0041792)

Process

Not Available

Role

Biological role

Carcinogenic agent (HMDB: HMDB0041792)
Mutagen (HMDB: HMDB0041792)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-108.9 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.74 mg/mL at 25 °C	Not Available
LogP	1.99	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.98 g/L	ALOGPS
logP	1.94	ALOGPS
logP	1.63	ChemAxon
logS	-1.7	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	20.29 m³·mol⁻¹	ChemAxon
Polarizability	6.7 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	117.627	30932474
DeepCCS	[M-H]-	115.732	30932474
DeepCCS	[M-2H]-	151.077	30932474
DeepCCS	[M+Na]+	125.484	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,3-Butadiene	C=CC=C	523.3	Standard polar	33892256
1,3-Butadiene	C=CC=C	388.6	Standard non polar	33892256
1,3-Butadiene	C=CC=C	389.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 1,3-Butadiene EI-B (Non-derivatized)	splash10-0ufr-9000000000-cddbfceffd529008d5ec	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,3-Butadiene EI-B (Non-derivatized)	splash10-0ufr-9000000000-cddbfceffd529008d5ec	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,3-Butadiene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-9000000000-e4f51ef2fbf933007d39	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,3-Butadiene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-9000000000-cfc5558b93570d1d78c0	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Butadiene 10V, Positive-QTOF	splash10-0a4i-9000000000-805abc61b7c8de6c5789	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Butadiene 20V, Positive-QTOF	splash10-0a4i-9000000000-805abc61b7c8de6c5789	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Butadiene 40V, Positive-QTOF	splash10-0a4i-9000000000-46aa55de9e12fa462b49	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Butadiene 10V, Negative-QTOF	splash10-0udi-9000000000-191296d0bc49a4a79c02	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Butadiene 20V, Negative-QTOF	splash10-0udi-9000000000-191296d0bc49a4a79c02	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Butadiene 40V, Negative-QTOF	splash10-0udi-9000000000-7031b766ca514dc531b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Butadiene 10V, Negative-QTOF	splash10-0udi-9000000000-0d737e29499be7940207	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Butadiene 20V, Negative-QTOF	splash10-0udi-9000000000-0d737e29499be7940207	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Butadiene 40V, Negative-QTOF	splash10-0udi-9000000000-0d737e29499be7940207	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Butadiene 10V, Positive-QTOF	splash10-0a4i-9000000000-1924391f943e092b4486	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Butadiene 20V, Positive-QTOF	splash10-0a4i-9000000000-c60974066ebc2547dd57	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Butadiene 40V, Positive-QTOF	splash10-0f79-9000000000-45337fddf4aab37b4ba0	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00011553

Chemspider ID

7557

KEGG Compound ID

C16450

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

1,3-Butadiene

METLIN ID

Not Available

PubChem Compound

7845

PDB ID

Not Available

ChEBI ID

39478

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1146751

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [PubMed:22282407 ]

Showing metabocard for 1,3-Butadiene (HMDB0041792)

MOL for HMDB0041792 (1,3-Butadiene)

3D MOL for HMDB0041792 (1,3-Butadiene)

3D SDF for HMDB0041792 (1,3-Butadiene)

3D-SDF for HMDB0041792 (1,3-Butadiene)

PDB for HMDB0041792 (1,3-Butadiene)

3D PDB for HMDB0041792 (1,3-Butadiene)

SMILES for HMDB0041792 (1,3-Butadiene)

INCHI for HMDB0041792 (1,3-Butadiene)

Structure for HMDB0041792 (1,3-Butadiene)

3D Structure for HMDB0041792 (1,3-Butadiene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra