Showing Compound Card for Fenchyl alcohol (CDB000607)

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Record Information
Version1.0
Created at2020-03-19 00:46:23 UTC
Updated at2020-12-07 19:07:34 UTC
CannabisDB IDCDB000607
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameFenchyl alcohol
DescriptionFenchyl alcohol, also known as fenchol, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings. Fenchol or 1,3,3-trimethyl-2-norbornanol is a monoterpenoid and an isomer of borneol. 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 the plastids. 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. It is a colorless or white solid. It occurs widely in nature. The naturally occurring enantiopure (1R)-endo-(+)-fenchol is used extensively in perfumery. Fenchol gives basil its characteristic scent (DOI: Ref:DOI ) and comprises 15.9% of the volatile oils of some species of Aster ( Ref:DOI ). Fenchyl alcohol has also been detected as a volatile component in cannabis plant samples ( PMID: 6991645 , 26657499 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,3,3-Trimethyl-2-norbornanolMeSH
endo-FencholMeSH
FencholMeSH
Fenchol, ((endo)-(+-))-isomerMeSH
Fenchol, ((exo)-(+-))-isomerMeSH
Fenchol, (1R-endo)-isomerMeSH
Fenchol, (1S-endo)-isomerMeSH
Fenchol, (1S-exo)-isomerMeSH
Fenchol, (endo)-isomerMeSH
Fenchol, (exo)-isomerMeSH
Fenchyl alcoholMeSH
Chemical FormulaC10H18O
Average Molecular Weight154.25
Monoisotopic Molecular Weight154.1358
IUPAC Name(1R,2R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
Traditional Name(1R,2R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
CAS Registry Number2217-02-9
SMILES
CC1(C)[C@H]2CC[C@](C)(C2)[C@H]1O
InChI Identifier
InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m0/s1
InChI KeyIAIHUHQCLTYTSF-OYNCUSHFSA-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
  • Fenchane monoterpenoid
  • Bicyclic monoterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point39 to 45 °CWikipedia
Boiling Point201 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.3ALOGPS
logP2.15ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-0.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.16 m³·mol⁻¹ChemAxon
Polarizability18.51 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSFenchyl alcohol, non-derivatized, GC-MS Spectrumsplash10-001i-9100000000-d1740c27ff7b86a0b13cSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0900000000-ed507d1b1719e12edbc12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-1900000000-0fe0191c4bde6f56fa8c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05aa-9500000000-f103d6927c834ced27782016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-d7f7c5b94ca90ef600002016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-4ebc0294913d58ac18f52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fe0-2900000000-b92c9da7506b101aadc12016-08-03View Spectrum
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 Quantified0.13 mg/g dry wt
    • David S. Wishart,...
 details
Alien Dawg (Indica dominant)Detected and Quantified0.24 +/- 0.04 mg/g dry wt
    • David S. Wishart,...
 details
ChemdogDetected and Quantified0.5 +/- 0.3 mg/g dry wt details
Crown OgDetected and Quantified0.6 +/- 0.1 mg/g dry wt details
GabriolaDetected and Quantified0.45 mg/g dry wt
    • David S. Wishart,...
 details
GasDetected and Quantified0.6 +/- 0.1 mg/g dry wt details
GelatoDetected and Quantified1 +/- 0.1 mg/g dry wt details
Island HoneyDetected and Quantified0.03 mg/g dry wt
    • David S. Wishart,...
 details
Miami White KushDetected and Quantified0.8 +/- 0.3 mg/g dry wt details
Og KushDetected and Quantified0.5 +/- 0.4 mg/g dry wt details
QuadraDetected and Quantified0.59 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.06 mg/g dry wt
    • David S. Wishart,...
 details
Sensi Star (Pure Indica)Detected and Quantified0.07 +/- 0.00 mg/g dry wt
    • David S. Wishart,...
 details
SherbertDetected and Quantified0.6 +/- 0.3 mg/g dry wt details
Skywalker Og KushDetected and Quantified0.6 +/- 0.3 mg/g dry wt details
Superman Og KushDetected and Quantified0.6 +/- 0.1 mg/g dry wt details
Tahoe Og KushDetected and Quantified0.6 +/- 0.1 mg/g dry wt details
Tangerine DreamDetected and Quantified0.06 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine Dream (Sativa dominant)Detected and Quantified0.06 +/- 0.00 mg/g dry wt
    • David S. Wishart,...
 details
Triple ODetected and Quantified0.7 +/- 0.2 mg/g dry wt 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 Compound6997371
PDB IDNot Available
ChEBI IDNot Available
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. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]