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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:09:08 UTC
Update Date2019-07-23 06:20:18 UTC
HMDB IDHMDB0036083
Secondary Accession Numbers
  • HMDB36083
Metabolite Identification
Common NameCarveol
DescriptionCarveol, also known as fema 2247, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Carveol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862818
Synonyms
ValueSource
5-Isopropenyl-2-methyl-2-cyclohexen-1-olChEBI
p-Mentha-1,8-dien-6-olChEBI
p-Mentha-6,8-dien-2-olChEBI
1-Methyl-4-isopropenyl-6-cyclohexen-2-olHMDB
2-Methyl-5(1-methylethenyl)cyclohex-2-ene-1-olHMDB
2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-olHMDB
2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-olHMDB
2-Methyl-5-isopropenyl-2-cyclohexen-1-olHMDB
2-Methyl-5-[1-methylethenyl]-2-cyclohexen-1-olHMDB
5-Isopropenyl-2-methylcyclohex-2-en-1-olHMDB
6,8-p-Menthadien-2-olHMDB
FEMA 2247HMDB
p-Mentha-1(6),8-dien-2-olHMDB
Chemical FormulaC10H16O
Average Molecular Weight152.237
Monoisotopic Molecular Weight152.120115135
IUPAC Name2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol
Traditional Namecarveol
CAS Registry Number99-48-9
SMILES
CC(=C)C1CC=C(C)C(O)C1
InChI Identifier
InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9-11H,1,5-6H2,2-3H3
InChI KeyBAVONGHXFVOKBV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.12Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.82 g/LALOGPS
logP2.41ALOGPS
logP1.99ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)18.21ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48 m³·mol⁻¹ChemAxon
Polarizability18.34 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9300000000-c0df06475a23b1847e64Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a5c-9400000000-20e9d5aa724b146ecbe0Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9300000000-c0df06475a23b1847e64Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a5c-9400000000-20e9d5aa724b146ecbe0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gc9-9200000000-d270baae0672bddf4630Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-059l-9420000000-c8fe9a59dae7a88e5d86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-1900000000-6cbdaa00e43b6a5f1466Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-7900000000-b55dc6268bf1d9facfabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9200000000-82efaa1d3034c0a127adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-63662b96265d54ab95acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-fb53bb25a46fab88d48aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0frl-6900000000-b30096dc2484f9341f67Spectrum
MSMass Spectrum (Electron Ionization)splash10-00kf-9600000000-b8936fad384c0f501d3aSpectrum
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 IDFDB014919
KNApSAcK IDC00010883
Chemspider ID7160
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarveol
METLIN IDNot Available
PubChem Compound7438
PDB IDNot Available
ChEBI ID23046
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.