Record Information
Version1.0
Created at2020-03-18 23:24:44 UTC
Updated at2020-12-07 19:07:06 UTC
CannabisDB IDCDB000099
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCamphene
DescriptionCamphene, also known as 2,2-dimethyl-3-methylenebicyclo[2.2.1]heptane or 2,2-dimethyl-3-methylenenorbornane, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Camphene is nearly insoluble in water but very soluble in common organic solvents. It volatilizes readily at room temperature and has a pungent smell. It exists as a flammable, white solid that has a minty, citrus, eucalyptus odor. It is produced industrially by catalytic isomerization of the more common alpha-pinene. Camphene is used in the preparation of fragrances and in food additives for flavouring. In the mid-19th century it was used as a fuel for lamps, but this was limited by its explosiveness. Camphene exists in all eukaryotes, ranging from yeast to plants to humans. Camphene can be found in a number of food items such as dill, carrots, caraway, hyssop, lemon, orange, nutmeg seed, parsley, sage, thyme, turmeric and fennel, which makes camphene a potential biomarker for the consumption of these food products. It is a minor constituent of many essential oils such as turpentine, cypress oil, camphor oil, citronella oil, neroli, ginger oil, and valerian. Camphene is one of several monoterpenes that are found in cannabis plants (PMID: 6991645 ).
Structure
Thumb
Synonyms
ValueSource
(+)-CompheneChEBI
(1R)-2,2-Dimethyl-3-methylenebicyclo[2.2.1]heptaneChEBI
(1R,4S)-(+)-CampheneChEBI
(1R,4S)-2,2-Dimethyl-3-methylenebicyclo[2.2.1]heptaneChEBI
(1R,4S)-CampheneChEBI
D-CampheneChEBI
(+)-CamphenePhytoBank
(1R)-CamphenePhytoBank
(±)-CamphenePhytoBank
2,2-Dimethyl-3-methylenenorbornanePhytoBank
2-Methylene-3,3-dimethylbicyclo[2.2.1]heptanePhytoBank
3,3-Dimethyl-2-methylenenorbornanePhytoBank
3,3-Dimethyl-2-methylenenorcamphanePhytoBank
dl-CamphenePhytoBank
Chemical FormulaC10H16
Average Molecular Weight136.23
Monoisotopic Molecular Weight136.1252
IUPAC Name(1R,4S)-2,2-dimethyl-3-methylidenebicyclo[2.2.1]heptane
Traditional Name(+)-camphene
CAS Registry Number5794-03-6
SMILES
CC1(C)[C@@H]2CC[C@@H](C2)C1=C
InChI Identifier
InChI=1S/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3/t8-,9+/m0/s1
InChI KeyCRPUJAZIXJMDBK-DTWKUNHWSA-N
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
Substituents
  • 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
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point51 - 52 °CWikipedia
Boiling Point159 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.56ALOGPS
logP2.86ChemAxon
logS-3.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.65 m³·mol⁻¹ChemAxon
Polarizability16.95 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-196b02102f0ebf09b534Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2900000000-c52b7cd8940e2fb05c54Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-6f9543516068b727c156Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-cce5a3a8054b82bf623fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-cce5a3a8054b82bf623fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2900000000-3b379a5acd27d5e4086cSpectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
8-Ball KushDetected and Quantified0.171 mg/g dry wt details
9 Lb HammerDetected and Quantified0.09 mg/g dry wt details
97 SageDetected and Quantified0.144 mg/g dry wt details
AdonisDetected and Quantified0.109 mg/g dry wt details
Alien DawgDetected and Quantified0.03 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Alien Dawg (Indica dominant)Detected and Quantified0.05 +/- 0.00 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Black BossDetected and Quantified0.123 mg/g dry wt details
Blue DreamDetected and Quantified0.067 mg/g dry wt details
ChemdawgDetected and Quantified0.075 mg/g dry wt details
Chemdawg #4Detected and Quantified0.077 mg/g dry wt details
Chemdawg #4Detected and Quantified0.122 mg/g dry wt details
Cookies and CreamDetected and Quantified0.095 mg/g dry wt details
Cosmic LotusDetected and Quantified0.061 mg/g dry wt details
FLODetected and Quantified0.054 mg/g dry wt details
GabriolaDetected and Quantified0.1 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Goji OGDetected and Quantified0.129 mg/g dry wt details
Gorilla GlueDetected and Quantified0.076 mg/g dry wt details
Gorilla Glue #4Detected and Quantified0.087 mg/g dry wt details
Hash PlantDetected and Quantified0.088 mg/g dry wt details
JabberwockyDetected and Quantified0.109 mg/g dry wt details
JabberwockyDetected and Quantified0.138 mg/g dry wt details
Lemon OGDetected and Quantified0.072 mg/g dry wt details
Lemon SkunkDetected and Quantified0.057 mg/g dry wt details
Lemon SkunkDetected and Quantified0.135 mg/g dry wt details
Liberty HazeDetected and Quantified0.099 mg/g dry wt details
Lucky CharmsDetected and Quantified0.15 mg/g dry wt details
Maui HazeDetected and Quantified0.099 mg/g dry wt details
Moby DickDetected and Quantified0.078 mg/g dry wt details
Pipe DreamDetected and Quantified0.108 mg/g dry wt details
Platinum DelightDetected and Quantified0.073 mg/g dry wt details
Purple EclipseDetected and Quantified0.087 mg/g dry wt details
QuadraDetected and Quantified0.06 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Rocket FuelDetected and Quantified0.113 mg/g dry wt details
Rollex OGDetected and Quantified0.195 mg/g dry wt details
Rosetta StoneDetected and Quantified0.1 mg/g dry wt details
Sensi StarDetected and Quantified0.01 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Strawberry FieldsDetected and Quantified0.094 mg/g dry wt details
Sunset SherbetDetected and Quantified0.064 mg/g dry wt details
Tangerine DreamDetected and Quantified0.02 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Venom OGDetected and Quantified0.091 mg/g dry wt details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001453
KNApSAcK IDC00000818
Chemspider IDNot Available
KEGG Compound IDC06304
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92221
PDB IDNot Available
ChEBI ID20
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. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]