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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:09:32 UTC
Update Date2019-07-23 06:34:27 UTC
HMDB IDHMDB0041469
Secondary Accession Numbers
  • HMDB41469
Metabolite Identification
Common NameDihydrocarveol acetate
DescriptionDihydrocarveol acetate, also known as 8-p-menthen-2-yl acetate or carhydrine, 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. Dihydrocarveol acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563863667
Synonyms
ValueSource
Dihydrocarveol acetic acidGenerator
(-)-Dihydrocarvyl acetateHMDB
2-Methyl-5-(1-methylethenyl)cyclohexyl acetateHMDB
2-Methyl-5-(prop-1-en-2-yl)cyclohexyl acetateHMDB
5-Isopropenyl-2-methylcyclohexyl acetateHMDB
8-p-Menthen-2-yl acetateHMDB
CarhydrineHMDB
Dihydrocarveyl acetateHMDB
Dihydrocarvyl acetateHMDB
FEMA 2380HMDB
Iso-dihydrocarvyl acetateHMDB
Isodihydrocarveol, acetateHMDB
Neo-isodihydrocarveol, acetateHMDB
p-Menth-8(9)-en-2-yl acetateHMDB
p-Menth-8-en-2-ol, acetateHMDB
p-Menth-8-en-2-yl acetateHMDB
p-Mentha-8-en-2-ol-acetateHMDB
Tuberyl acetateHMDB
2-Methyl-5-(prop-1-en-2-yl)cyclohexyl acetic acidGenerator
Chemical FormulaC12H20O2
Average Molecular Weight196.286
Monoisotopic Molecular Weight196.146329884
IUPAC Name2-methyl-5-(prop-1-en-2-yl)cyclohexyl acetate
Traditional Namedihydrocarvyl acetate
CAS Registry Number20777-49-5
SMILES
CC1CCC(CC1OC(C)=O)C(C)=C
InChI Identifier
InChI=1S/C12H20O2/c1-8(2)11-6-5-9(3)12(7-11)14-10(4)13/h9,11-12H,1,5-7H2,2-4H3
InChI KeyTUSIZTVSUSBSQI-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
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
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
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP3.46ALOGPS
logP2.76ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.37 m³·mol⁻¹ChemAxon
Polarizability23.09 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-9300000000-9beb866d9483e92bb89aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1900000000-0a05dddfff8d65051dd8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052s-4900000000-5fb6bb7348b393a55bf4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067i-9100000000-facf36cf931cb5c50270Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-1900000000-3e96e81756a8bb940372Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-2900000000-2ef85f875545afcb0d97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k9l-6900000000-6b47596f472174553a53Spectrum
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 IDFDB021427
KNApSAcK IDC00035825
Chemspider ID28089
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound30248
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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.