Record Information
Version1.0
Creation date2010-04-08 22:11:22 UTC
Update date2019-11-26 03:10:24 UTC
Primary IDFDB014599
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(S)-Carvone
DescriptionConstituent of dill (Anethum graveolens) and caraway (Carum carvi) 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 Number2244-16-8
Structure
Thumb
Synonyms
SynonymSource
(-)-(4R)-CarvoneChEBI
(-)-(R)-CarvoneChEBI
(-)-p-Mentha-6,8-dien-2-oneChEBI
(4R)-CarvoneChEBI
(5R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-oneChEBI
(R)-(-)-CarvoneChEBI
(R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-oneChEBI
(R)-5-Isopropenyl-2-methylcyclohex-2-en-1-oneChEBI
L-1-Methyl-4-isopropenyl-6-cyclohexen-2-oneChEBI
L-CarvoneChEBI
L-p-Mentha-1(6),8-dien-2-oneChEBI
Levo-carvoneChEBI
(-)-CarvoneHMDB
(4R)-(-)-CarvoneHMDB
(R)-(-)-p-Mentha-6,8-dien-2-oneHMDB
2-Methyl-5-(1-methylethenyl)-(R)-2-cyclohexen-1-oneHMDB
L(-)-CarvoneHMDB
(+)-(4S)-carvonebiospider
(+)-(s)-carvonebiospider
(+)-carvonbiospider
(+)-carvonebiospider
(4S)-carvonebiospider
(4S)-p-mentha-1(6),8-dien-2-onebiospider
(5S)-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-onebiospider
(5S)-2-methyl-5-(1-methylethenyl)cyclohex-2-en-1-onebiospider
(5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-onebiospider
(s)-(+)-carvonebiospider
(S)-(+)-p-mentha-6,8-dien- 2-onebiospider
(S)-(+)-p-mentha-6,8-dien-2-onebiospider
(S)-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-onebiospider
(S)-2-methyl-5-(1-methylvinyl)cyclohex-2-en-1-onebiospider
(S)-5-Isopropenyl-2-methyl-2-cyclohexenonebiospider
(S)-5-isopropenyl-2-methylcyclohex-2-en-1-onebiospider
(s)-carvonebiospider
(S)-d-p-Mentha-6,8,(9)-dien-2-onebiospider
2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (5S)-biospider
2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (S)-biospider
Carvone, (+)-biospider
D-(+)-carvonebiospider
d-1-Methyl-4-isopropenyl-6-cyclohexen-2-onebiospider
D-carvonebiospider
D-p-mentha-6,8,(9)-dien-2-onebiospider
D-P-Mentha-6,8(9)-dien-2-oneHMDB
D(+)-carvonebiospider
p-Mentha-6,8-dien-2-one, (S)-(+)-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
BioavailabilityYesChemAxon
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 KeyULDHMXUKGWMISQ-SECBINFHSA-N
Isomeric SMILESCC(=C)[C@@H]1CC=C(C)C(=O)C1
Average Molecular Weight150.2176
Monoisotopic Molecular Weight150.10446507
Classification
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
OntologyNo ontology term
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°DFC
Experimental Water Solubility1.3 mg/mL at 18 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP1.267
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +61.2DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-9300000000-0663a3956cbefc28418aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-9300000000-0663a3956cbefc28418aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-9300000000-0663a3956cbefc28418aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-9300000000-0663a3956cbefc28418aJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f83-9200000000-e9569993e9ab3a8d9c56JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ , positive (Annotated)splash10-052f-9600000000-9902205f6d338c08818dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udi-0900000000-52f6355f33c4b2243d8aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0udi-0900000000-cb6bd893e3059c4e749aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0udi-0900000000-12445f07d9581bb79ba9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0zfr-0900000000-f9115bab64084ca3e9c6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0zfr-0900000000-c2cc2f68aa635d48f7d2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0pb9-0900000000-34673104b5cbea631ccaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0a4i-0900000000-3c5bc016004147d81ac1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0a4i-0900000000-805c8d6f02a70e4d8cedJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0a4i-1900000000-90f1a3149285030d18d3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-0a4i-4900000000-c900c93dbadd576b2e03JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-0a4l-9700000000-ccd0df21a8aba540288cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-052f-9400000000-b05876718fef3d10e1e6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-00kf-9200000000-97e06bb63f72b6a871e6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-0a4i-0900000000-62d73cc97ac426baf5d8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-004l-9000000000-672e06fb3b7870b5e066JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-001i-9000000000-a5c95a778293e816e298JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-000t-9100000000-c3c9a32c71b3929313ebJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-9000000000-fb41d95361a6747c1394JSpectraViewer | MoNA
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
MSMass Spectrum (Electron Ionization)splash10-0f8c-9200000000-88f46d943b306bc533dbJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID15855
ChEMBL IDCHEMBL501949
KEGG Compound IDC11383
Pubchem Compound ID16724
Pubchem Substance IDNot Available
ChEBI ID15399
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04487
CRC / DFC (Dictionary of Food Compounds) IDJSX52-Q:JSW31-E
EAFUS IDNot Available
Dr. Duke IDD-CARVONE|(+)-CARVONE|D-(+)-CARVONE
BIGG IDNot Available
KNApSAcK IDC00010891
HET ID0WU
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID2244-16-8
GoodScent IDrw1007121
SuperScent ID16724
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 / Bioactivities
DescriptorIDDefinitionReference
acetylcholinesterase inhibitor38462 An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.DUKE
anti acetylcholinesterase38462 An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.DUKE
anti Alzheimeran52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti cholinesterase37733 An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).DUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
caraway
  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
  2. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  3. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spice
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bread
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
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.