Showing Compound Card for Carvone (CDB000086)

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Record Information
Version1.0
Created at2020-03-18 23:24:15 UTC
Updated at2020-12-07 19:07:05 UTC
CannabisDB IDCDB000086
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCarvone
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 a volatile terpenoid found in cannabis plants (PMID: 6991645 ). 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).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-(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
Chemical FormulaC10H14O
Average Molecular Weight150.22
Monoisotopic Molecular Weight150.1045
IUPAC Name(5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one
Traditional Name(-)-carvone
CAS Registry Number6485-40-1
SMILES
CC(=C)[C@@H]1CC=C(C)C(=O)C1
InChI Identifier
InChI=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
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 15 °CNot Available
Boiling Point231 °CWikipedia
Water Solubility1.31 mg/mL at 25 °CNot Available
logP2.71Not Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0f8c-9200000000-88f46d943b306bc533db2015-03-01View Spectrum
GC-MSCarvone, non-derivatized, GC-MS Spectrumsplash10-0a59-9300000000-0663a3956cbefc28418aSpectrum
GC-MSCarvone, non-derivatized, GC-MS Spectrumsplash10-0a59-9300000000-0663a3956cbefc28418aSpectrum
GC-MSCarvone, non-derivatized, GC-MS Spectrumsplash10-0a59-9300000000-0663a3956cbefc28418aSpectrum
GC-MSCarvone, non-derivatized, GC-MS Spectrumsplash10-0a59-9300000000-0663a3956cbefc28418aSpectrum
Predicted GC-MSCarvone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f83-9200000000-e9569993e9ab3a8d9c56Spectrum
Predicted GC-MSCarvone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCarvone, 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
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0035089
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013718
KNApSAcK IDC00000807
Chemspider ID388655
KEGG Compound IDC01767
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439570
PDB IDNot Available
ChEBI ID15400
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [PubMed:5556886 ]
  3. Inglik N, Rudenko BA, Kakhnovskii IM, Koroleva TV: [Gas chromatographic study of the composition of the volatile components of the urine in normal subjects and patients with diabetes mellitus]. Lab Delo. 1989;(8):24-7. [PubMed:2477620 ]