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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:18:32 UTC
Update Date2022-03-07 02:55:10 UTC
HMDB IDHMDB0037066
Secondary Accession Numbers
  • HMDB37066
Metabolite 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 an extremely weak basic (essentially neutral) compound (based on its pKa). beta-Caryophyllene alcohol is an earthy, moss, and spicy tasting compound. Outside of the human body, beta-caryophyllene alcohol has been detected, but not quantified in, several different foods, such as citrus, fruits, herbs and spices, and pepper (spice). This could make beta-caryophyllene alcohol a potential biomarker for the consumption of these foods.
Structure
Data?1563862971
Synonyms
ValueSource
b-Caryophyllene alcoholGenerator
Β-caryophyllene alcoholGenerator
4,4,8-Trimethyl-tricyclo(6.3.1.02,5)dodecan-1-olHMDB
4,4,8-Trimethyltricyclo(6.3.1.02,5)dodecan-1-olHMDB
4,4,8-Trimethyltricyclo[6.3.1.02,5]dodecan-1-ol, 9ciHMDB
Caryolan-1-olHMDB
CaryophyllenolHMDB
beta-Caryophyllene alcoholMeSH
Chemical FormulaC15H26O
Average Molecular Weight222.3663
Monoisotopic Molecular Weight222.198365454
IUPAC Name4,4,8-trimethyltricyclo[6.3.1.0²,⁵]dodecan-1-ol
Traditional Name4,4,8-trimethyltricyclo[6.3.1.0²,⁵]dodecan-1-ol
CAS Registry Number472-97-9
SMILES
CC1(C)CC2C1CCC1(C)CCCC2(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
InChI KeyFUQAYSQLAOJBBC-UHFFFAOYSA-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 Descriptors
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point94 - 96 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0093 g/LALOGPS
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
Polarizability27.43 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+151.97631661259
DarkChem[M-H]-149.6131661259
DeepCCS[M+H]+157.00830932474
DeepCCS[M-H]-154.6530932474
DeepCCS[M-2H]-189.10530932474
DeepCCS[M+Na]+164.29430932474
AllCCS[M+H]+154.232859911
AllCCS[M+H-H2O]+150.632859911
AllCCS[M+NH4]+157.732859911
AllCCS[M+Na]+158.632859911
AllCCS[M-H]-161.632859911
AllCCS[M+Na-2H]-162.032859911
AllCCS[M+HCOO]-162.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
beta-Caryophyllene alcoholCC1(C)CC2C1CCC1(C)CCCC2(O)C12195.4Standard polar33892256
beta-Caryophyllene alcoholCC1(C)CC2C1CCC1(C)CCCC2(O)C11629.6Standard non polar33892256
beta-Caryophyllene alcoholCC1(C)CC2C1CCC1(C)CCCC2(O)C11634.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
beta-Caryophyllene alcohol,1TMS,isomer #1CC12CCCC(O[Si](C)(C)C)(C1)C1CC(C)(C)C1CC21763.1Semi standard non polar33892256
beta-Caryophyllene alcohol,1TBDMS,isomer #1CC12CCCC(O[Si](C)(C)C(C)(C)C)(C1)C1CC(C)(C)C1CC22010.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - beta-Caryophyllene alcohol GC-MS (Non-derivatized) - 70eV, Positivesplash10-06tf-3920000000-b68753a0c64ca8112abc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Caryophyllene alcohol GC-MS (1 TMS) - 70eV, Positivesplash10-0v7r-5290000000-2abb69265dc4b41e9d832017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Caryophyllene alcohol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene alcohol 10V, Positive-QTOFsplash10-0ab9-0090000000-f722d04da4e967382a9b2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene alcohol 20V, Positive-QTOFsplash10-0ab9-1290000000-68742d2f6dacdd03ba4c2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene alcohol 40V, Positive-QTOFsplash10-054x-8910000000-6d5494cbf7239c6a62882016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene alcohol 10V, Negative-QTOFsplash10-00di-0090000000-df53e329d8b4cb3216602016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene alcohol 20V, Negative-QTOFsplash10-00di-0090000000-78f3f8caa5d303c302f12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene alcohol 40V, Negative-QTOFsplash10-0a4i-3950000000-68721e6a300ef023c3c02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene alcohol 10V, Negative-QTOFsplash10-00di-0090000000-ab61d8a2af41e6ed2e492021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene alcohol 20V, Negative-QTOFsplash10-00di-0090000000-ab61d8a2af41e6ed2e492021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene alcohol 40V, Negative-QTOFsplash10-00di-0090000000-ab61d8a2af41e6ed2e492021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene alcohol 10V, Positive-QTOFsplash10-00di-1290000000-b8ad223195b98618f7332021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene alcohol 20V, Positive-QTOFsplash10-0ac0-9660000000-c0162b1be56a39c1cd112021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Caryophyllene alcohol 40V, Positive-QTOFsplash10-00l6-9100000000-768051f4547352e86ab42021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB016050
KNApSAcK IDC00021969
Chemspider ID55073
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound61125
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .