Showing Compound Card for trans-beta-Farnesene (CDB000352)

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Record Information
Version1.0
Created at2020-03-19 00:32:28 UTC
Updated at2020-12-07 19:07:23 UTC
CannabisDB IDCDB000352
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Nametrans-beta-Farnesene
Description(E)-Beta-Farnesene, also known as EBF or trans-beta-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. The beta isomer exists as two stereoisomers (cis and trans) about the geometry of its central double bond. However, only the trans isomer exists in nature. Beta-Farnesene exists as a clear colorless liquid and is a hydrophobic, neutral compound that is insoluble in water. It has a woody, sweet, citrus aroma and is used as a masking or perfuming agent. Beta-Farnesene is found naturally in many plants and plant essential oils including basil, blood orange, carrots, celery, ginger, grapefruit, lavender, mint, orange peel, parsley, peppermint, pine, rosemary and thyme. It is one of several sesquiterpenes that are found in cannabis plants (PMID: 6991645 ). It is also found in cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ). Beta-Farnesene is also released by aphids as an alarm pheremone upon death to warn away other aphids (PMID: 21092302 )
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(6E)-7,11-Dimethyl-3-methylene-1,6,10-dodecatrieneChEBI
(e)-7,11-Dimethyl-3-methylenedodeca-1,6,10-trieneChEBI
beta-FarneseneChEBI
beta-trans-FarneseneChEBI
trans-7,11-Dimethyl-3-methylene-1,6,10-dodecatrieneChEBI
b-FarneseneGenerator
Β-farneseneGenerator
b-trans-FarneseneGenerator
Β-trans-farneseneGenerator
(e)-b-FarneseneGenerator
(e)-Β-farneseneGenerator
(E)-beta-FarneseneChEBI, KEGG
trans-b-FarneseneGenerator
trans-β-FarneseneGenerator
(E)-7,11-Dimethyl-3-methylene-1,6,10-dodecatrienePhytoBank
trans-beta-FarnesenePhytoBank
Chemical FormulaC15H24
Average Molecular Weight204.36
Monoisotopic Molecular Weight204.1878
IUPAC Name(6E)-7,11-dimethyl-3-methylidenedodeca-1,6,10-triene
Traditional Nameβ-farnesene
CAS Registry Number18452-58-9
SMILES
CC(C)=CCC\C(C)=C\CCC(=C)C=C
InChI Identifier
InChI=1S/C15H24/c1-6-14(4)10-8-12-15(5)11-7-9-13(2)3/h6,9,12H,1,4,7-8,10-11H2,2-3,5H3/b15-12+
InChI KeyJSNRRGGBADWTMC-NTCAYCPXSA-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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0034 g/lALOGPS
logP5.70ALOGPS
Predicted Properties
PropertyValueSource
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
Polarizability26.89 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS7,11-Dimethyl-3-methylene-1,6E,10-dodecatriene, non-derivatized, GC-MS Spectrumsplash10-00kf-9100000000-0de28d2b36d20fb36076Spectrum
GC-MS7,11-Dimethyl-3-methylene-1,6E,10-dodecatriene, non-derivatized, GC-MS Spectrumsplash10-014l-9100000000-f65ac7d94ccd703ca91dSpectrum
GC-MS7,11-Dimethyl-3-methylene-1,6E,10-dodecatriene, non-derivatized, GC-MS Spectrumsplash10-00kf-9300000000-b9d4d3c4eb1b8ad6bb3dSpectrum
GC-MS7,11-Dimethyl-3-methylene-1,6E,10-dodecatriene, non-derivatized, GC-MS Spectrumsplash10-00kf-9100000000-0de28d2b36d20fb36076Spectrum
GC-MS7,11-Dimethyl-3-methylene-1,6E,10-dodecatriene, non-derivatized, GC-MS Spectrumsplash10-014l-9100000000-f65ac7d94ccd703ca91dSpectrum
GC-MS7,11-Dimethyl-3-methylene-1,6E,10-dodecatriene, non-derivatized, GC-MS Spectrumsplash10-00kf-9300000000-b9d4d3c4eb1b8ad6bb3dSpectrum
Predicted GC-MS7,11-Dimethyl-3-methylene-1,6E,10-dodecatriene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01bi-9800000000-3bc4e66181d2648448f2Spectrum
Predicted GC-MS7,11-Dimethyl-3-methylene-1,6E,10-dodecatriene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified1.54 mg/g dry wt
    • David S. Wishart,...
 details
Alien Dawg (Indica dominant)Detected and Quantified4.22 +/- 0.27 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified3.1 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified1.01 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified2.21 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine Dream (Sativa dominant)Detected and Quantified3.57 +/- 0.17 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0062763
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00003131
Chemspider IDNot Available
KEGG Compound IDC09666
BioCyc IDCPD-8239
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281517
PDB IDNot Available
ChEBI ID10418
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Kunert G, Reinhold C, Gershenzon J: Constitutive emission of the aphid alarm pheromone, (E)-beta-farnesene, from plants does not serve as a direct defense against aphids. BMC Ecol. 2010 Nov 23;10:23. doi: 10.1186/1472-6785-10-23. [PubMed:21092302 ]
  3. Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. [PubMed:19932496 ]
  4. Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. [PubMed:17710406 ]