Showing Compound Card for beta-Caryophyllene alcohol (CDB000213)

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Record Information
Version1.0
Created at2020-03-19 00:24:49 UTC
Updated at2020-11-18 16:34:55 UTC
CannabisDB IDCDB000213
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namebeta-Caryophyllene alcohol
Descriptionbeta-Caryophyllene alcohol, also known as caryolan-1-ol or caryophyllenol, belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H). beta-Caryophyllene alcohol is a neutral compound. beta-Caryophyllene alcohol is a naturally occurring organic compound derived from Caryophyllene. beta-Caryophyllene alcohol has an earthy, moss, and spicy odor ( Ref:DOI ). beta-Caryophyllene alcohol has been detected in grapefruit juice, black pepper cornmint, and oils from bergamot, hinoki root (2.61%), hinoki wood (1.49%), hop and palmarosa ( Ref:DOI ). This could make beta-caryophyllene alcohol a potential biomarker for the consumption of these foods. beta-Caryophyllene alcohol was a tertiary alcohol detected in cannabis (PMID: 6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC15H26O
Average Molecular Weight222.37
Monoisotopic Molecular Weight222.1984
IUPAC Name(1S,2S,5R,8R)-4,4,8-trimethyltricyclo[6.3.1.0^{2,5}]dodecan-1-ol
Traditional Name(1S,2S,5R,8R)-4,4,8-trimethyltricyclo[6.3.1.0^{2,5}]dodecan-1-ol
CAS Registry Number472-97-9
SMILES
CC1(C)C[C@H]2[C@H]1CC[C@@]1(C)CCC[C@]2(O)C1
InChI Identifier
InChI=1S/C15H26O/c1-13(2)9-12-11(13)5-8-14(3)6-4-7-15(12,16)10-14/h11-12,16H,4-10H2,1-3H3/t11-,12+,14-,15+/m1/s1
InChI KeyFUQAYSQLAOJBBC-OSRDXIQISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentTertiary alcohols
Alternative Parents
Substituents
  • Tertiary alcohol
  • Cyclic alcohol
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.52ALOGPS
logP3.43ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)-0.19ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity66.5 m³·mol⁻¹ChemAxon
Polarizability27.39 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSbeta-Caryophyllene alcohol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
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
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
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 CompoundNot Available
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 ]