Record Information
Created at2020-03-19 00:30:03 UTC
Updated at2020-12-07 19:07:20 UTC
CannabisDB IDCDB000306
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Nameα-trans-bergamotene
Descriptionα-Trans-bergamotene belongs to the class of organic compounds known as bicyclic sesquiterpenoids. These are sesquiterpenoids containing exactly two rings, which are fused together. α-Trans-bergamotene is formally classified as a polycyclic hydrocarbon although it is biochemically a sesquiterpene as it synthesized via multiple isoprene units. 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. 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. There are four known Bergamotene isomers including α-cis-, α-trans-, β-cis- and β-trans-bergamotene. α-trans-bergamotene is a neutral, hydrophobic molecule that is insoluble in water. It exists as a clear, greenish oil that has a woody or warm tea-like odor. It is found in the fruits and essential oils of anise, basil, cumin, carrot, bergamot, lime, lemon, cottonseed, nutmeg, black pepper and kumquat. α-trans-bergamotene is also found in the essential oils of plants such as tobacco (PMID:28434859 ) and cannabis (PMID:6991645 ). It is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ). Isomers of bergamotene have a function as pheromones for some insect species. Evidence suggests that plants under attack by herbivore insects are able to release specific amounts of bergamotene to attract natural enemies of the insect herbivores, using these sesquiterpenes as a defense mechanism (PMID: 16418295 ). More specifically, the tobacco plant emits α-trans-bergamotene from its flowers at night to attract the tobacco hawk moth (Manduca sexta) as a pollinator; however, during the day the leaves produce α-trans-bergamotene to lure predatory insects to feed on any larvae and eggs that the pollinator may have produced (PMID: 28434859 ).
Chemical FormulaC15H24
Average Molecular Weight204.36
Monoisotopic Molecular Weight204.1878
IUPAC Name(1S,5S,6R)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene
Traditional Name(-)-trans-α-bergamotene
CAS Registry Number13474-59-4
InChI Identifier
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
  • Pinane monoterpenoid
  • Bicyclic monoterpenoid
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors

Industrial application:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity68.52 m³·mol⁻¹ChemAxon
Polarizability26.45 ųChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
EI-MS/GC-MSNot Available
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.28 mg/g dry wt
    • David S. Wishart,...
GabriolaDetected and Quantified0.32 mg/g dry wt
    • David S. Wishart,...
Island HoneyDetected and Quantified0.14 mg/g dry wt
    • David S. Wishart,...
QuadraDetected and Quantified0.19 mg/g dry wt
    • David S. Wishart,...
Sensi StarDetected and Quantified0.16 mg/g dry wt
    • David S. Wishart,...
Tangerine DreamDetected and Quantified0.29 mg/g dry wt
    • David S. Wishart,...
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6429302
PDB IDNot Available
ChEBI ID62756
General References
  1. Zhou W, Kugler A, McGale E, Haverkamp A, Knaden M, Guo H, Beran F, Yon F, Li R, Lackus N, Kollner TG, Bing J, Schuman MC, Hansson BS, Kessler D, Baldwin IT, Xu S: Tissue-Specific Emission of (E)-alpha-Bergamotene Helps Resolve the Dilemma When Pollinators Are Also Herbivores. Curr Biol. 2017 May 8;27(9):1336-1341. doi: 10.1016/j.cub.2017.03.017. Epub 2017 Apr 20. [PubMed:28434859 ]
  2. 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 ]
  3. Schnee C, Kollner TG, Held M, Turlings TC, Gershenzon J, Degenhardt J: The products of a single maize sesquiterpene synthase form a volatile defense signal that attracts natural enemies of maize herbivores. Proc Natl Acad Sci U S A. 2006 Jan 24;103(4):1129-34. doi: 10.1073/pnas.0508027103. Epub 2006 Jan 17. [PubMed:16418295 ]