Record Information
Version1.0
Creation date2010-04-08 22:06:32 UTC
Update date2020-09-17 15:35:23 UTC
Primary IDFDB005121
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsoprene
DescriptionIsoprene, also known as 2-methyl-1,3-butadiene, 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. It is a common organic compound with the formula CH2=C(CH3)‚àíCH=CH2. In its pure form it is a colorless volatile liquid. It is produced by many plants and animals (including humans) and its polymers are the main component of natural rubber. C. G. Williams named the compound in 1860 after obtaining it from thermal decomposition (pyrolysis) of natural rubber. He correctly deduced the empirical formula C5H8 (https://doi.org/10.1098/rspl.1859.0101). Isoprene is produced and emitted by many species of trees (major producers are oaks, poplars, eucalyptus, and some legumes). Isoprene is made through the mevalonic acid pathway in the cytosol and also, in eubacteria, green algae and the plastids of superior plants, through the methyl-erythritol 4-phosphate pathway (MEP pathway, also called the non-mevalonate pathway). Isoprene has been detected, but not quantified, in a few different foods, such as carrots, sweet oranges, and wild carrots.
CAS Number78-79-5
Structure
Thumb
Synonyms
SynonymSource
2-Methyl-1,3-butadieneChEBI
2-MethylbutadieneChEBI
2-MethyldivinylChEBI
beta-MethylbivinylChEBI
CH2=C(CH3)CH=ch2ChEBI
IsopentadieneChEBI
IsoprenChEBI
IsoprenoChEBI
IsoterpeneChEBI
b-MethylbivinylGenerator
Β-methylbivinylGenerator
β-methylbivinylbiospider
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H8
IUPAC name2-methylbuta-1,3-diene
InChI IdentifierInChI=1S/C5H8/c1-4-5(2)3/h4H,1-2H2,3H3
InChI KeyRRHGJUQNOFWUDK-UHFFFAOYSA-N
Isomeric SMILESCC(=C)C=C
Average Molecular Weight68.117
Monoisotopic Molecular Weight68.062600256
Classification
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateliquid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point-145.9 oC
Boiling PointNot Available
Experimental Water Solubility0.642 mg/mL at 25 oCMCAULIFFE,C (1966)
Experimental logP2.42CHEMICALS INSPECTION AND TESTING INSTITU (
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-9000000000-aa7bf6693faf53f2c9f8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9000000000-79f5e8913a6e3948a925JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-cc71ad3e01e005b392f4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9000000000-c4e0cc5173528ae70b45JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9000000000-748a9309c1a76a36f582JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxr-9000000000-b24db55f64156fae0d1dJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-014i-9000000000-bcc7aa57f0fa0fd9d399JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC16521
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI ID35194
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDISOPRENE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).