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(R)-Carvone (FDB013718)

Record Information
Version1.0
Creation date2010-04-08 22:10:52 UTC
Update date2020-09-17 15:30:23 UTC
Primary IDFDB013718
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(R)-Carvone
DescriptionCarvone, with R and S isomers, 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. Carvone is a neutral compound. Carvone is a naturally occurring organic compound found in many essential oils but is most abundant in the oils from caraway seeds (Carum carvi), spearmint (Mentha spicata), and dill (PMID: 27427817). Carvone is occasionally found as a component of biological fluids in normal individuals. Both carvones (R, S) are used in the food and flavor industry (http//doi:10.1016/j.foodchem.2005.01.003). R-carvone is also used in air freshening products and in essential oils used in aromatherapy and alternative medicine. Caraway was used for medicinal purposes by the ancient Romans, but carvone was probably not isolated as a pure compound until Varrentrapp obtained it in 1841 (PMID: 5556886, 2477620). Carvone may help in the management of diseases (PMID: 30374904) and had been considered as an adjuvant for treatment of cancer patients (PMID: 30087792) and patients with epilepsy (PMID: 31239862). It also has been successfully used as a biopesticide (PMID: 30250476).
CAS Number6485-40-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 230-231°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
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 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
Food Biomarker OntologyNot Available
VMH 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.