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Record Information
Version3.6
Creation Date2006-08-13 19:43:36 UTC
Update Date2016-02-11 01:06:44 UTC
HMDB IDHMDB04487
Secondary Accession NumbersNone
Metabolite Identification
Common Name(+)-(S)-Carvone
DescriptionCarvone is a volatile terpenoid. Carvone is found in many essential oils and is very abundant in the seeds of caraway (Carum carvi). Carvone is occasionally found as a component of biological fluids in normal individuals. Caraway was used for medicinal purposes by the ancient Romans, but carvone was probably not isolated as a pure compound until Varrentrapp obtained it in1841. (PMID: 5556886 , 2477620 , Wikipedia).
Structure
Thumb
Synonyms
ValueSource
(+)-(4S)-CarvoneChEBI
(+)-(S)-CarvoneChEBI
(5S)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-oneChEBI
(S)-(+)-CarvoneChEBI
(S)-(+)-P-Mentha-6,8-dien-2-oneChEBI
(S)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-oneChEBI
(S)-2-Methyl-5-(1-methylvinyl)cyclohex-2-en-1-oneChEBI
(S)-5-Isopropenyl-2-methylcyclohex-2-en-1-oneChEBI
(S)-CarvoneChEBI
CarvolChEBI
CarvoneChEBI
D-(+)-CarvoneChEBI
D-CarvoneChEBI
(+)-CarvoneHMDB
2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-oneHMDB
D-P-Mentha-6,8(9)-dien-2-oneHMDB
Chemical FormulaC10H14O
Average Molecular Weight150.2176
Monoisotopic Molecular Weight150.10446507
IUPAC Name(5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one
Traditional Namecarvone, (+)-
CAS Registry Number2244-16-8
SMILES
CC(=C)[C@H]1CC=C(C)C(=O)C1
InChI Identifier
InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m0/s1
InChI KeyInChIKey=ULDHMXUKGWMISQ-VIFPVBQESA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Cyclic ketone
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point< 15 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1300 mg/L at 18 °CNot Available
LogP1.267Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.16 mg/mLALOGPS
logP2.77ALOGPS
logP2.55ChemAxon
logS-2.1ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.17 m3·mol-1ChemAxon
Polarizability17.65 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0pb9-0900000000-cad4b73ca0349a0fca73View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4l-9700000000-4f8b99aefc0ccf7e31f4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052f-9600000000-9902205f6d338c08818dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-300) , Positivesplash10-0a59-9200000000-b8485ca29dc163ef7386View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0kai-9200000000-87c2472a96aad69404afView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB014599
KNApSAcK IDC00010891
Chemspider ID15855
KEGG Compound IDC11383
BioCyc IDCPD-1089
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04487
Metagene LinkHMDB04487
METLIN IDNot Available
PubChem Compound16724
PDB ID0WU
ChEBI ID15399
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [5556886 ]
  2. Hahn I, Scherer PW, Mozell MM: A mass transport model of olfaction. J Theor Biol. 1994 Mar 21;167(2):115-28. [8207942 ]
  3. Jager W, Mayer M, Reznicek G, Buchbauer G: Percutaneous absorption of the montoterperne carvone: implication of stereoselective metabolism on blood levels. J Pharm Pharmacol. 2001 May;53(5):637-42. [11370703 ]
  4. Inglik N, Rudenko BA, Kakhnovskii IM, Koroleva TV: [Gas chromatographic study of the composition of the volatile components of the urine in normal subjects and patients with diabetes mellitus]. Lab Delo. 1989;(8):24-7. [2477620 ]