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Showing Compound (S)-Carvone (FDB014599)

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
MOLSDFPDBSMILESInChI
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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0f8c-9200000000-88f46d943b306bc533db2015-03-01View Spectrum
GC-MS(R)-Carvone, non-derivatized, GC-MS Spectrumsplash10-0a59-9300000000-0663a3956cbefc28418aSpectrum
GC-MS(R)-Carvone, non-derivatized, GC-MS Spectrumsplash10-0a59-9300000000-0663a3956cbefc28418aSpectrum
GC-MS(R)-Carvone, non-derivatized, GC-MS Spectrumsplash10-0a59-9300000000-0663a3956cbefc28418aSpectrum
GC-MS(R)-Carvone, non-derivatized, GC-MS Spectrumsplash10-0a59-9300000000-0663a3956cbefc28418aSpectrum
Predicted GC-MS(R)-Carvone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f83-9200000000-e9569993e9ab3a8d9c56Spectrum
Predicted GC-MS(R)-Carvone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(R)-Carvone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ , positive (Annotated)splash10-052f-9600000000-9902205f6d338c08818d2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udi-0900000000-52f6355f33c4b2243d8a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0udi-0900000000-cb6bd893e3059c4e749a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0udi-0900000000-12445f07d9581bb79ba92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0zfr-0900000000-f9115bab64084ca3e9c62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0zfr-0900000000-c2cc2f68aa635d48f7d22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0pb9-0900000000-34673104b5cbea631cca2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0a4i-0900000000-3c5bc016004147d81ac12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0a4i-0900000000-805c8d6f02a70e4d8ced2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0a4i-1900000000-90f1a3149285030d18d32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-0a4i-4900000000-c900c93dbadd576b2e032020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-0a4l-9700000000-ccd0df21a8aba540288c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-052f-9400000000-b05876718fef3d10e1e62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-00kf-9200000000-97e06bb63f72b6a871e62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-0a4i-0900000000-62d73cc97ac426baf5d82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-004l-9000000000-672e06fb3b7870b5e0662020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-001i-9000000000-a5c95a778293e816e2982020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-000t-9100000000-c3c9a32c71b3929313eb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-9000000000-fb41d95361a6747c13942020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-62861ac4cbf0b95e50692016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-5900000000-b282dcb5d4a98c3f852f2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-0fd631d26260645c64ae2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-97d37f99bcaf0ed7d1082016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-1817a8dceee7a31df4e02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-6900000000-581a45ee1ec95e2011382016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
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 agent that blocks the breakdown of acetylcholine, increasing its concentration and enhancing cholinergic transmission. Therapeutically, it improves cognitive function and muscle contraction, commonly used in managing Alzheimer's disease, myasthenia gravis, and glaucoma.DUKE
Anti acetylcholinesterase38462 An agent that inhibits acetylcholinesterase, increasing acetylcholine levels. It enhances cholinergic transmission, used therapeutically to treat Alzheimer's disease, myasthenia gravis, and glaucoma, improving cognitive function, muscle strength, and reducing intraocular pressure.DUKE
Anti-Alzheimeran52217 An agent that inhibits the progression of Alzheimer's disease, reducing beta-amyloid plaque formation and neuroinflammation. Therapeutically, it improves cognitive function and memory, commonly used in managing mild to moderate Alzheimer's disease and other neurodegenerative disorders.DUKE
Anti cholinesterase37733 An agent that inhibits acetylcholinesterase, increasing acetylcholine levels, and enhancing cholinergic transmission. Therapeutically, it's used to treat myasthenia gravis, glaucoma, and Alzheimer's disease, improving muscle strength, reducing eye pressure, and enhancing cognitive function.DUKE
Insecticide24852 An agent that kills or repels insects, used to control pests and prevent disease transmission. Therapeutically, insecticides have applications in public health and veterinary medicine, key medical uses include controlling insect-borne diseases such as malaria, typhus, and Lyme disease.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.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.