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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 21:08:06 UTC
Update Date2021-10-13 06:53:31 UTC
HMDB IDHMDB0036065
Secondary Accession Numbers
  • HMDB36065
Metabolite Identification
Common Namealpha-Farnesene
Descriptionalpha-Farnesene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (3E,6E)-alpha-Farnesene, also known as trans-alpha-Farnesene, is a sweet, bergamot, and citrus tasting flavouring ingredient. (3E,6E)-alpha-Farnesene is a constituent of the natural coating of apples and pears and other fruit. It has been identified in gingers, cottonseeds, common oregano, sweet oranges, spearmints, guava, pomes, and pears. This could make (3E,6E)-alpha-farnesene a potential biomarker for the consumption of these foods.
Structure
Data?1601234304
Synonyms
ValueSource
(3E,6E)-alpha-FarneseneChEBI
(3E,6E)-a-FarneseneGenerator
(3E,6E)-Α-farneseneGenerator
a-FarneseneGenerator
Α-farneseneGenerator
(E,E)-FarneseneHMDB
trans-FarneseneHMDB
3,7,11-Trimethyl-(E,E)-1,3,6,10-dodecatetraeneHMDB
alpha-trans,trans-FarneseneHMDB
trans,trans-alpha-FarneseneHMDB
alpha-FarneseneMeSH
(3E,6E)-3,7,11-Trimethyl-1,3,6,10-dodecatetraeneHMDB
(E,E)-alpha-FarneseneHMDB
(E,E)-α-FarneseneHMDB
3,7,11-Trimethyl-1,3,6,10-dodecatetraeneHMDB
FarneseneHMDB
trans,trans-α-FarneseneHMDB
trans-2,6,10-Trimethyl-2,6,9,11-dodecatetraeneHMDB
trans-3,7,11-Trimethyl-1,3,6,10-dodecatetraeneHMDB
trans-alpha-FarneseneHMDB
trans-α-FarneseneHMDB
Chemical FormulaC15H24
Average Molecular Weight204.3511
Monoisotopic Molecular Weight204.187800768
IUPAC Name(3E,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene
Traditional Namefarnesene
CAS Registry Number502-61-4
SMILES
CC(C)=CCC\C(C)=C\C\C=C(/C)C=C
InChI Identifier
InChI=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
Chemical Taxonomy
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

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point260.00 to 262.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.011 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.139 (est)The Good Scents Company Information System
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0052 g/LALOGPS
logP10(5.7) g/LALOGPS
logP10(5.14) g/LChemAxon
logS10(-4.6) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+154.30731661259
DarkChem[M-H]-154.14731661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Farnesene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0673-9800000000-2417bd57042b291e594e2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Farnesene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Farnesene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9300000000-3317cba9629f9379052f2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Farnesene 10V, Positive-QTOFsplash10-0a4i-3690000000-313b913d532cd4decec12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Farnesene 20V, Positive-QTOFsplash10-0pw9-9710000000-078e5a8d7e85822b7c0c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Farnesene 40V, Positive-QTOFsplash10-0uxr-9100000000-3d3f85f913cafb612d5c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Farnesene 10V, Negative-QTOFsplash10-0udi-0090000000-6d4cdcd69849df029e452016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Farnesene 20V, Negative-QTOFsplash10-0udi-0190000000-e363a25bab51e774a5922016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Farnesene 40V, Negative-QTOFsplash10-0kg9-4900000000-b4cda282a594b52f25392016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Farnesene 10V, Negative-QTOFsplash10-0udi-0190000000-fa0c676eabe0c49e322b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Farnesene 20V, Negative-QTOFsplash10-0udi-0390000000-0d353a60a5a97cd9c1a32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Farnesene 40V, Negative-QTOFsplash10-014i-4900000000-9f5bab6c0c653c72230e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Farnesene 10V, Positive-QTOFsplash10-060s-7910000000-05be940f3488abb12fe82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Farnesene 20V, Positive-QTOFsplash10-0a7l-9300000000-a54209dd2c1271d1d7d72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Farnesene 40V, Positive-QTOFsplash10-05ru-9000000000-a7b8e3b259690a16a4412021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014895
KNApSAcK IDC00003130
Chemspider ID4444849
KEGG Compound IDC09665
BioCyc IDCPD-8764
BiGG IDNot Available
Wikipedia LinkFarnesene
METLIN IDNot Available
PubChem Compound5281516
PDB IDNot Available
ChEBI ID10280
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1044061
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.