Record Information
Version1.0
Created at2020-03-19 00:52:35 UTC
Updated at2020-12-07 19:07:42 UTC
CannabisDB IDCDB000712
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Nametrans-beta-Caryophyllene
DescriptionTrans-caryophyllene or beta-caryophyllene (BCP), also known as just caryophelene, 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 (PMID: 7640522 ). However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-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. Beta-caryophyllene is considered to be an isoprenoid lipid molecule. Beta-caryophyllene is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. There are several isomers of caryophyllene including beta-caryophyllene (with cis and trans double bonds), alpha-caryophyllene (also known as alpha humulene) and gamma-caryophyllene or isocaryophyllene (the cis double-bond isomer). The first total synthesis of beta-caryophyllene was done in 1964 by E. J. Corey and was considered one of the classic demonstrations of the possibilities of synthetic organic chemistry at the time ( Ref:DOI ). Beta-caryophyllene exists as a pale, clear liquid and has a sweet, woody or spicy odor along with a clove, peppery or woody taste. Beta-caryophyllene can be used in cosmetics as a perfuming agent or in food as a flavoring agent. β-Caryophyllene is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves), the essential oil of Cannabis sativa (PMID: 29783790 ), rosemary, and hops. Trans-beta-Caryophyllene is a sweet and dry tasting compound that can be found in a number of food items such as allspice, figs, pot marjoram, and roman camomile, which makes beta-caryophyllene a potential biomarker for the consumption of these food products. Beta-caryophyllene is one of the chemical compounds that contributes to the aroma of black pepper (PMID: 12462618 ). Beta-caryophyllene is the most common sesquiterpene in cannabis plants and exhibits anti-inflammatory, cytoprotective (gastric mucosa), and antimalarial activities. Beta-caryophyllene is a functional non-psychoactive CB2 receptor agonist (PMID: 26965491 ) and has shown analgesic, anti-inflammatory, neuroprotective, anti-depressive, anxiolytic and anti-nephtotoxicity effects in a number of studies (PMID: 28368293 ). More recently Beta caryophyllene has been shown to inhibit microglial cells, CD4+ and CD8+ T lymphocytes, as well as protein expression of pro-inflammatory cytokines in a murine model of multiple sclerosis. This led to a suppression of motor paralysis and neuroinflammation in the MS-affected animals (PMID: 28368293 ).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC15H24
Average Molecular Weight204.36
Monoisotopic Molecular Weight204.1878
IUPAC Name(1S,4Z,9R)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
Traditional Name(1S,4Z,9R)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
CAS Registry Number10579-93-8
SMILES
C\C1=C\CCC(=C)[C@@H]2CC(C)(C)[C@H]2CC1
InChI Identifier
InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6-/t13-,14-/m0/s1
InChI KeyNPNUFJAVOOONJE-BJLYVFBQSA-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
  • Caryophyllane sesquiterpenoid
  • Sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.35ALOGPS
logP4.52ChemAxon
logS-4.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity67.45 m³·mol⁻¹ChemAxon
Polarizability26.16 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
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
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified1.86 mg/g dry wt
    • David S. Wishart,...
details
Alien Dawg (Indica dominant)Detected and Quantified2.24 +/- 0.05 mg/g dry wt
    • David S. Wishart,...
details
GabriolaDetected and Quantified2.37 mg/g dry wt
    • David S. Wishart,...
details
Island HoneyDetected and Quantified1.32 mg/g dry wt
    • David S. Wishart,...
details
QuadraDetected and Quantified1.02 mg/g dry wt
    • David S. Wishart,...
details
Sensi StarDetected and Quantified0.78 mg/g dry wt
    • David S. Wishart,...
details
Sensi Star (Pure Indica)Detected and Quantified0.68 +/- 0.01 mg/g dry wt
    • David S. Wishart,...
details
Tangerine DreamDetected and Quantified0.85 mg/g dry wt
    • David S. Wishart,...
details
Tangerine Dream (Sativa dominant)Detected and Quantified0.80 +/- 0.03 mg/g dry wt
    • David S. Wishart,...
details
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 Compound5452236
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
  2. Pavlovic R, Nenna G, Calvi L, Panseri S, Borgonovo G, Giupponi L, Cannazza G, Giorgi A: Quality Traits of "Cannabidiol Oils": Cannabinoids Content, Terpene Fingerprint and Oxidation Stability of European Commercially Available Preparations. Molecules. 2018 May 20;23(5). pii: molecules23051230. doi: 10.3390/molecules23051230. [PubMed:29783790 ]
  3. Jirovetz L, Buchbauer G, Ngassoum MB, Geissler M: Aroma compound analysis of Piper nigrum and Piper guineense essential oils from Cameroon using solid-phase microextraction-gas chromatography, solid-phase microextraction-gas chromatography-mass spectrometry and olfactometry. J Chromatogr A. 2002 Nov 8;976(1-2):265-75. doi: 10.1016/s0021-9673(02)00376-x. [PubMed:12462618 ]
  4. Sharma C, Al Kaabi JM, Nurulain SM, Goyal SN, Kamal MA, Ojha S: Polypharmacological Properties and Therapeutic Potential of beta-Caryophyllene: A Dietary Phytocannabinoid of Pharmaceutical Promise. Curr Pharm Des. 2016;22(21):3237-64. doi: 10.2174/1381612822666160311115226. [PubMed:26965491 ]
  5. Alberti TB, Barbosa WL, Vieira JL, Raposo NR, Dutra RC: (-)-beta-Caryophyllene, a CB2 Receptor-Selective Phytocannabinoid, Suppresses Motor Paralysis and Neuroinflammation in a Murine Model of Multiple Sclerosis. Int J Mol Sci. 2017 Apr 1;18(4). pii: ijms18040691. doi: 10.3390/ijms18040691. [PubMed:28368293 ]
  6. 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 ]