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(3E,6E)-alpha-Farnesene (FDB014895)

Record Information
Version1.0
Creation date2010-04-08 22:11:32 UTC
Update date2020-09-17 15:32:36 UTC
Primary IDFDB014895
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(3E,6E)-alpha-Farnesene
DescriptionTrans-trans-alpha-Farnesene, also known as (3E,6E)-alpha-Farnesene, belongs to the class of organic compounds known as sesquiterpenoids. Sesquiterpenes 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-erythritol-phosphate (MEP) pathway in the cytosol. The term farnesene refers to a set of six closely related chemical compounds (4 alpha-Farnesenes and 2 Beta-Farnesenes) which all are sesquiterpenes. α-Farnesene and β-Farnesene are isomers, differing by the location of one double bond. β-Farnesene is 7,11-dimethyl-3-methylene-1,6,10-dodecatriene while α-Farnesene is 3,7,11-trimethyl-1,3,6,10-dodecatetraene. There are four known Alpha-farnesene stereoisomers which differ about the geometry of two of its three internal double bonds (the stereoisomers of the third internal double bond are identical). (3E,6E)-alpha-Farnesene is one of the 4 isomers of Alpha-farnesene and is the most common isomer, Trans-trans-alpha-Farnesene is a hydrophobic, neutral molecule that is not water soluble. It has a woody, bergamot, green and citrus like aroma and a fresh, green, fruity taste. Trans-trans-alpha-Farnesene is used as a flavoring and perfuming agent. It is found in the coating of apples, and other fruits, and it is responsible for the characteristic green apple odour (doi:10.1038/2101260a0). (3E,6E)-alpha-Farnesene is found within a few different foods, such as gingers, cottonseeds, common oregano and sweet oranges. (3E,6E)-alpha-Farnesene has also been detected, but not quantified in, several different foods, such as apples, pears, spearmints, guava, and carrots.
CAS Number502-61-4
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0052 g/LALOGPS
logP5.7ALOGPS
logP5.14ChemAxon
logS-4.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity73.25 m³·mol⁻¹ChemAxon
Polarizability26.86 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H24
IUPAC name(3E,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene
InChI IdentifierInChI=1S/C15H24/c1-6-14(4)10-8-12-15(5)11-7-9-13(2)3/h6,9-10,12H,1,7-8,11H2,2-5H3/b14-10+,15-12+
InChI KeyCXENHBSYCFFKJS-VDQVFBMKSA-N
Isomeric SMILESCC(C)=CCC\C(C)=C\C\C=C(/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:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 88.16%; H 11.84%DFC
Melting Point< 25 oC
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)splash10-0006-9300000000-3317cba9629f9379052f2015-03-01View Spectrum
Predicted GC-MS(3E,6E)-alpha-Farnesene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0673-9800000000-2417bd57042b291e594eSpectrum
Predicted GC-MS(3E,6E)-alpha-Farnesene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3E,6E)-alpha-Farnesene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-3690000000-313b913d532cd4decec12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pw9-9710000000-078e5a8d7e85822b7c0c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9100000000-3d3f85f913cafb612d5c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-6d4cdcd69849df029e452016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-e363a25bab51e774a5922016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kg9-4900000000-b4cda282a594b52f25392016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0190000000-fa0c676eabe0c49e322b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0390000000-0d353a60a5a97cd9c1a32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-4900000000-9f5bab6c0c653c72230e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-060s-7910000000-05be940f3488abb12fe82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a7l-9300000000-a54209dd2c1271d1d7d72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ru-9000000000-a7b8e3b259690a16a4412021-09-22View Spectrum
NMR
TypeDescriptionView
ChemSpider ID4444849
ChEMBL IDCHEMBL3182226
KEGG Compound IDC09665
Pubchem Compound ID5281516
Pubchem Substance IDNot Available
ChEBI ID10280
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36066
CRC / DFC (Dictionary of Food Compounds) IDJXF60-O:JXF61-P
EAFUS ID1333
Dr. Duke IDTRANS-ALPHA-FARNESENE|FARNESENE|TRANS,TRANS-ALPHA-FARNESENE
BIGG IDNot Available
KNApSAcK IDC00003130
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID502-61-4
GoodScent IDrw1044061
SuperScent ID5281516
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 / Bioactivities
DescriptorIDDefinitionReference
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
pheromone26013 A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
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
lavender
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
lime
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
citrus
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bergamot
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
myrrh
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
neroli
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
green
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.