Carvone (YMDB01648)

Identification
YMDB IDYMDB01648
NameCarvone
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
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
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (-)-(4R)-carvone
  • (-)-(R)-carvone
  • (-)-Carvone
  • (-)-p-mentha-6,8-dien-2-one
  • (4R)-Carvone
  • (5R)-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one
  • (R)-(-)-carvone
  • (R)-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one
  • (R)-5-isopropenyl-2-methylcyclohex-2-en-1-one
  • l-1-methyl-4-isopropenyl-6-cyclohexen-2-one
  • l-carvone
  • l-p-mentha-1(6),8-dien-2-one
  • levo-carvone
  • 1-Carvone
  • 2-Methyl-5-(1-methyl-1-ethenyl)-2-cyclohexen-1-one
  • 2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-one
  • 2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-enone
  • 2-Methyl-5-isopropenyl-2-cyclohexenone
  • 5-Isopropenyl-2-methylcyclohex-2-en-1-one
  • Carvol
  • Carvon
  • Karvon
  • p-Mentha-6,8-dien-2-one
  • (RS)-5-Isopropenyl-2-methylcyclohex-2-en-1-one
  • Carvone, (R)-isomer
  • Limonen-6-one
  • 2-Methyl-5-(1-methylethenyl)-2-cyclohexene-1-one
  • 5-Isopropyl-2-methyl-2-cyclohexen-1-one
  • Carvone, (S)-isomer
CAS number6485-40-1
WeightAverage: 150.2176
Monoisotopic: 150.10446507
InChI KeyULDHMXUKGWMISQ-UHFFFAOYSA-N
InChIInChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3
IUPAC Name2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one
Traditional IUPAC Namecarvone
Chemical FormulaC10H14O
SMILESCC(=C)C1CC=C(C)C(=O)C1
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
Physical Properties
StateSolid
Charge0
Melting point< 25 °C
Experimental Properties
PropertyValueReference
Water Solubility1.31 mg/mL at 25 oC [SUZUKI,T (1991)]PhysProp
LogP2.71 [GRIFFIN,S ET AL. (1999)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.16 g/LALOGPS
logP2.77ALOGPS
logP2.55ChemAxon
logS-2.1ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
BasilFDB014587
FennelFDB014587
LicoriceFDB014587
MintFDB014587
MintyFDB014587
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f8c-9100000000-64d2436851c170c3898aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4l-3900000000-1935fc84143fcf43b855JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4l-4900000000-856f6fa492156b47d6abJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f8c-9100000000-64d2436851c170c3898aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4l-3900000000-1935fc84143fcf43b855JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4l-4900000000-856f6fa492156b47d6abJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f8l-9200000000-0d07518eb09c4d6d7512JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-62861ac4cbf0b95e5069JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-5900000000-b282dcb5d4a98c3f852fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-0fd631d26260645c64aeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-97d37f99bcaf0ed7d108JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-1817a8dceee7a31df4e0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-6900000000-581a45ee1ec95e201138JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-22917433edc8ad9dbc2eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-c0270d719fd67ba328d9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001j-9700000000-dfa5cb40b47870793316JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-3900000000-f279f95a33eb225c1b14JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07eg-9400000000-34f0a30acb50659192b6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mo-9000000000-7b658cbdc17dd03f44edJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0kai-9100000000-ea28fdf9d5478ea50fe2JSpectraViewer | MoNA
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15400
HMDB IDHMDB0035824
Pubchem Compound ID7439
Kegg IDC01767
ChemSpider ID21106424
FOODB IDFDB014587
Wikipedia IDCarvone
BioCyc IDNot Available