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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 20:50:52 UTC
Update Date2021-09-14 15:45:30 UTC
HMDB IDHMDB0035824
Secondary Accession Numbers
  • HMDB35824
Metabolite Identification
Common NameCarvone
DescriptionCarvone, also known as carvol or limonen-6-one, 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. Based on a literature review a significant number of articles have been published on Carvone.
Structure
Data?1563862777
Synonyms
ValueSource
1-CarvoneChEBI
2-Methyl-5-(1-methyl-1-ethenyl)-2-cyclohexen-1-oneChEBI
2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-oneChEBI
2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-enoneChEBI
2-Methyl-5-isopropenyl-2-cyclohexenoneChEBI
5-Isopropenyl-2-methylcyclohex-2-en-1-oneChEBI
CarvolChEBI
CarvonChEBI
KarvonChEBI
p-Mentha-6,8-dien-2-oneChEBI
(RS)-5-Isopropenyl-2-methylcyclohex-2-en-1-oneHMDB
Carvone, (R)-isomerHMDB
Limonen-6-oneHMDB
2-Methyl-5-(1-methylethenyl)-2-cyclohexene-1-oneHMDB
5-Isopropyl-2-methyl-2-cyclohexen-1-oneHMDB
Carvone, (S)-isomerHMDB
Chemical FormulaC10H14O
Average Molecular Weight150.221
Monoisotopic Molecular Weight150.104465071
IUPAC Name2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one
Traditional Namecarvone
CAS Registry Number22327-39-5
SMILES
CC(=C)C1CC=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
InChI KeyULDHMXUKGWMISQ-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
  • Cyclohexenone
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.16 g/LALOGPS
logP10(2.77) g/LALOGPS
logP10(2.55) g/LChemAxon
logS10(-2.1) g/LALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.17 m³·mol⁻¹ChemAxon
Polarizability17.66 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+135.11931661259
DarkChem[M-H]-130.26831661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CarvoneCC(=C)C1CC=C(C)C(=O)C11704.5Standard polar33892256
CarvoneCC(=C)C1CC=C(C)C(=O)C11221.6Standard non polar33892256
CarvoneCC(=C)C1CC=C(C)C(=O)C11235.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Carvone,1TMS,isomer #1C=C(C)C1C=C(O[Si](C)(C)C)C(C)=CC11381.4Semi standard non polar33892256
Carvone,1TMS,isomer #1C=C(C)C1C=C(O[Si](C)(C)C)C(C)=CC11350.4Standard non polar33892256
Carvone,1TBDMS,isomer #1C=C(C)C1C=C(O[Si](C)(C)C(C)(C)C)C(C)=CC11619.2Semi standard non polar33892256
Carvone,1TBDMS,isomer #1C=C(C)C1C=C(O[Si](C)(C)C(C)(C)C)C(C)=CC11525.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Carvone EI-B (Non-derivatized)splash10-0f8c-9100000000-64d2436851c170c3898a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Carvone GC-EI-TOF (Non-derivatized)splash10-0a4l-3900000000-1935fc84143fcf43b8552017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Carvone GC-EI-TOF (Non-derivatized)splash10-0a4l-4900000000-856f6fa492156b47d6ab2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Carvone EI-B (Non-derivatized)splash10-0f8c-9100000000-64d2436851c170c3898a2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Carvone GC-EI-TOF (Non-derivatized)splash10-0a4l-3900000000-1935fc84143fcf43b8552018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Carvone GC-EI-TOF (Non-derivatized)splash10-0a4l-4900000000-856f6fa492156b47d6ab2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carvone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f8l-9200000000-0d07518eb09c4d6d75122016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carvone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0kai-9100000000-ea28fdf9d5478ea50fe22015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvone 10V, Positive-QTOFsplash10-0udi-0900000000-62861ac4cbf0b95e50692016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvone 20V, Positive-QTOFsplash10-0udi-5900000000-b282dcb5d4a98c3f852f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvone 40V, Positive-QTOFsplash10-1000-9100000000-0fd631d26260645c64ae2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvone 10V, Negative-QTOFsplash10-0002-0900000000-97d37f99bcaf0ed7d1082016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvone 20V, Negative-QTOFsplash10-0002-0900000000-1817a8dceee7a31df4e02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvone 40V, Negative-QTOFsplash10-001l-6900000000-581a45ee1ec95e2011382016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvone 10V, Negative-QTOFsplash10-0002-0900000000-22917433edc8ad9dbc2e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvone 20V, Negative-QTOFsplash10-0002-0900000000-c0270d719fd67ba328d92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvone 40V, Negative-QTOFsplash10-001j-9700000000-dfa5cb40b478707933162021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvone 10V, Positive-QTOFsplash10-0a4i-3900000000-f279f95a33eb225c1b142021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvone 20V, Positive-QTOFsplash10-07eg-9400000000-34f0a30acb50659192b62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvone 40V, Positive-QTOFsplash10-00mo-9000000000-7b658cbdc17dd03f44ed2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014587
KNApSAcK IDC00035062
Chemspider ID21106424
KEGG Compound IDNot Available
BioCyc IDCarvones
BiGG IDNot Available
Wikipedia LinkCarvone
METLIN IDNot Available
PubChem Compound7439
PDB IDNot Available
ChEBI ID38265
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1228101
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.