Record Information
Version1.0
Creation date2010-04-08 22:10:52 UTC
Update date2015-07-20 23:01:51 UTC
Primary IDFDB013718
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(R)-Carvone
DescriptionConstit. of spearmint (Mentha crispa) costmary, kuromoji and other oils. Flavouring ingredient Carvone 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)
CAS Number6485-40-1
Structure
Thumb
Synonyms
SynonymSource
(-)-(4R)-CarvoneChEBI
(-)-(r)-carvonebiospider
(-)-carvonebiospider
(-)-p-Mentha-6,8-dien-2-onebiospider
(4R)-(-)-Carvonebiospider
(4R)-CarvoneChEBI
(5R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-oneChEBI
(R)-(-)-CarvoneChEBI
(R)-(-)-P-Mentha-6,8-dien-2-oneHMDB
(R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-oneChEBI
(R)-5-Isopropenyl-2-methylcyclohex-2-en-1-oneChEBI
(r)-carvonebiospider
2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (R)-biospider
2-Methyl-5-(1-methylethenyl)-(R)-2-cyclohexen-1-oneHMDB
L-1-Methyl-4-isopropenyl-6-cyclohexen-2-oneChEBI
L-CarvoneChEBI
L-P-Mentha-1(6),8-dien-2-oneChEBI
L(-)-carvonebiospider
Levo-carvonebiospider
p-Mentha-6,8-dien-2-one, (R)-(-)-biospider
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
Polarizability17.65 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H14O
IUPAC name(5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one
InChI IdentifierInChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m1/s1
InChI KeyInChIKey=ULDHMXUKGWMISQ-SECBINFHSA-N
Isomeric SMILESCC(=C)[C@@H]1CC=C(C)C(=O)C1
Average Molecular Weight150
Monoisotopic Molecular Weight150
Classification
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassPrenol lipids
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 79.96%; H 9.39%; O 10.65%DFC
Melting Point<15 oC
Boiling PointBp 230-231°DFC
Experimental Water Solubility1.31 mg/mL at 25 oCSUZUKI,T (1991)
Experimental logP2.71GRIFFIN,S ET AL. (1999)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -62.46DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-9300000000-0663a3956cbefc28418aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f83-9200000000-e9569993e9ab3a8d9c56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-62861ac4cbf0b95e5069View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-5900000000-b282dcb5d4a98c3f852fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-0fd631d26260645c64aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-97d37f99bcaf0ed7d108View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-1817a8dceee7a31df4e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-6900000000-581a45ee1ec95e201138View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0f8c-9200000000-88f46d943b306bc533dbView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID388655
ChEMBL IDCHEMBL2229268
KEGG Compound IDC01767
Pubchem Compound ID439570
Pubchem Substance IDNot Available
ChEBI ID15400
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35089
CRC / DFC (Dictionary of Food Compounds) IDJSX52-Q:JGG35-A
EAFUS IDNot Available
Dr. Duke ID(-)-CARVONE
BIGG IDNot Available
KNApSAcK IDC00000807
HET IDNot Available
Flavornet ID6485-40-1
GoodScent IDrw1002741
SuperScent ID439570
Wikipedia IDCarvone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
mint
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
minty
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spearmint
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.