Record Information
Version1.0
Creation date2010-04-08 22:11:25 UTC
Update date2020-09-17 15:32:36 UTC
Primary IDFDB014702
Secondary Accession Numbers
  • FDB014703
  • FDB014704
Chemical Information
FooDB Namebeta-Farnesene
Descriptionβ-Farnesene, also known as (Z)-β-farnesene or β-cis-farnesene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. β-Farnesene is 7,11-dimethyl-3-methylene-1,6,10-dodecatriene. beta-Farnesene exists as two stereoisomers about the geometry of its central double bond. β-Farnesene has one naturally occurring isomer. The E isomer is a constituent of various essential oils. It is also released by aphids as an alarm pheremone upon death to warn away other aphids. Several plants, including potato species, have been shown to emit this terpenoid as a natural insect repellent. β-Farnesene is a sweet, citrus, and green tasting compound.
CAS Number28973-97-9
Structure
Thumb
Synonyms
SynonymSource
(6Z)-7,11-Dimethyl-3-methylene-1,6,10-dodecatrieneChEBI
(Z)-beta-FarneseneChEBI
beta-(Z)-FarneseneChEBI
beta-cis-FarneseneChEBI
(Z)-b-FarneseneGenerator
(Z)-Β-farneseneGenerator
b-(Z)-FarneseneGenerator
Β-(Z)-farneseneGenerator
b-cis-FarneseneGenerator
Β-cis-farneseneGenerator
b-FarneseneGenerator
Β-farneseneGenerator
7,11-Dimethyl-3-methylene-1,6,10-dodecatrieneHMDB
cis-b-FarneseneGenerator
cis-Β-farneseneGenerator
beta-FarneseneMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.0034 g/LALOGPS
logP5.7ALOGPS
logP5.2ChemAxon
logS-4.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity72.18 m³·mol⁻¹ChemAxon
Polarizability26.75 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H24
IUPAC name(6Z)-7,11-dimethyl-3-methylidenedodeca-1,6,10-triene
InChI IdentifierInChI=1S/C15H24/c1-6-14(4)10-8-12-15(5)11-7-9-13(2)3/h6,9,12H,1,4,7-8,10-11H2,2-3,5H3/b15-12-
InChI KeyJSNRRGGBADWTMC-QINSGFPZSA-N
Isomeric SMILESCC(C)=CCC\C(C)=C/CCC(=C)C=C
Average Molecular Weight204.3511
Monoisotopic Molecular Weight204.187800768
Classification
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Farsesane sesquiterpenoid
  • Sesquiterpenoid
  • Alkatetraene
  • Branched unsaturated hydrocarbon
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Acyclic olefin
  • Hydrocarbon
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 88.16%; H 11.84%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00kf-9200000000-8fe9965c757993a3da3cSpectrum
Predicted GC-MSbeta-Farnesene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06dr-9800000000-0cf1a88b3286d23cfee8Spectrum
Predicted GC-MSbeta-Farnesene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2590000000-97aec58a39dbd95191c2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0api-9820000000-5cfce39fed14f59cb32cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9100000000-b58552bbf4bf6991f239Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-8679dd3e5f4e50a4cdedSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-6ebdcd800d0f42496ce2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kg9-4900000000-74d9a26b7a0e990038ebSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0290000000-452458c093084cfa4678Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00mn-5900000000-43455a50f927d4e73685Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-060s-9710000000-994d4c69028890070859Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a7l-9300000000-4a11eb2cdd00336af5afSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lgl-9100000000-0525b6ed5a080a68463bSpectrum
NMR
TypeDescriptionView
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJVC34-G:JVC34-G
EAFUS IDNot Available
Dr. Duke ID(3)-BETA-FARNESENE
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
Flavours
FlavorCitations
citrus
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
green
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
wood
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
sweet
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
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).