Isoprene (CHEM003185)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 05:54:33 UTC
Update Date2026-04-17 19:10:23 UTC
Accession NumberCHEM003185
Identification
Common NameIsoprene
ClassSmall Molecule
DescriptionIsoprene, or 2-methyl-1,3-butadiene, is a common organic compound with the formula CH2=C(CH3)CH=CH2. It is a colorless volatile liquid. Isoprene is produced by many plants. Isoprene is incorporated into and helps stabilize cell membranes in response to heat stress, conferring some tolerance to heat spikes. Isoprene is able to cause toxic effects in the testis of rats and at multiple organ sites in mice.
Contaminant Sources
  • Clean Air Act Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • Tobacco Smoke Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Cigarette Toxin
  • Food Toxin
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-Methyl-1,3-butadieneChEBI
2-MethylbutadieneChEBI
2-MethyldivinylChEBI
beta-MethylbivinylChEBI
CH2=C(CH3)CH=ch2ChEBI
IsopentadieneChEBI
IsoprenChEBI
IsoprenoChEBI
IsoterpeneChEBI
b-MethylbivinylGenerator
Β-methylbivinylGenerator
Chemical FormulaC5H8
Average Molecular Mass68.117 g/mol
Monoisotopic Mass68.063 g/mol
CAS Registry Number78-79-5
IUPAC Name2-methylbuta-1,3-diene
Traditional Nameisoprene
SMILESCC(=C)C=C
InChI IdentifierInChI=1S/C5H8/c1-4-5(2)3/h4H,1-2H2,3H3
InChI KeyRRHGJUQNOFWUDK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as branched unsaturated hydrocarbons. These are hydrocarbons that contains one or more unsaturated carbon atoms, and an aliphatic branch.
KingdomOrganic compounds
Super ClassHydrocarbons
ClassUnsaturated hydrocarbons
Sub ClassBranched unsaturated hydrocarbons
Direct ParentBranched unsaturated hydrocarbons
Alternative Parents
Substituents
  • Branched unsaturated hydrocarbon
  • Alkadiene
  • Unsaturated aliphatic hydrocarbon
  • Olefin
  • Acyclic olefin
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Actin Cytoskeleton
  • Cell surface
  • Cytoplasm
  • Cytosol
  • Dendritic Process
  • Endoplasmic reticulum
  • Extracellular
  • Extracellular matrix
  • Golgi apparatus
  • Lysosome
  • Membrane Fraction
  • Microsome
  • Mitochondrial Membrane
  • Mitochondrion
  • Perinuclear region
  • Peroxisomal Membrane
  • Peroxisome
  • Plasma Membrane
  • Soluble Fraction
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Carbon MetabolismNot AvailableNot Available
Metabolic PathwaysNot AvailableNot Available
ApoptosisNot Availablemap04210
Hmg Coa Reductase InhibitorsNot AvailableNot Available
Nitrogen MetabolismNot AvailableNot Available
Carotenoid BiosynthesisNot AvailableNot Available
Retinol MetabolismSMP00074 map00830
Dna replicationNot Availablemap03030
Terpenoid backbone biosynthesisNot Availablemap00900
Sphingolipid MetabolismSMP00034 map00600
Purine MetabolismSMP00050 map00230
Influenza aNot Availablemap05164
Fatty acid MetabolismSMP00051 map00071
Fatty Acid BiosynthesisSMP00456 map00061
Diterpenoid BiosynthesisNot AvailableNot Available
Cell cycleNot Availablemap04110
Biosynthesis Of Secondary MetabolitesNot AvailableNot Available
Antifungal AgentsNot AvailableNot Available
Allograft RejectionNot AvailableNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-143.95°C
Boiling Point34.067°C
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.8 g/LALOGPS
logP2.22ALOGPS
logP1.88ChemAxon
logS-1.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity24.58 m³·mol⁻¹ChemAxon
Polarizability8.58 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-9000000000-aa7bf6693faf53f2c9f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9000000000-79f5e8913a6e3948a925Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-cc71ad3e01e005b392f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9000000000-c4e0cc5173528ae70b45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9000000000-748a9309c1a76a36f582Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxr-9000000000-b24db55f64156fae0d1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-9000000000-13c3d4b2254b96312f2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9000000000-182e8f0f63d0901250e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-7b7c61918e48120c38a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9000000000-87c1aff470916cc07239Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9000000000-87c1aff470916cc07239Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-9000000000-7033f85bf44b5b1856d1Spectrum
MSMass Spectrum (Electron Ionization)splash10-014i-9000000000-bcc7aa57f0fa0fd9d399Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (2)
Uses/SourcesThis is a toxic chemical found in cigarettes or generated by tobacco combustion.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0253673
FooDB IDFDB005121
Phenol Explorer IDNot Available
KNApSAcK IDC00046784
BiGG IDNot Available
BioCyc IDCPD-9436
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIsoprene
Chemspider ID6309
ChEBI ID35194
PubChem Compound ID6557
Kegg Compound IDC16521
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17921528
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19011917
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=8690002