Record Information
Version1.0
Creation date2010-04-08 22:11:32 UTC
Update date2019-11-26 03:10:55 UTC
Primary IDFDB014915
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(1R,4R)-Dihydrocarvone
Description(1r,4r)-dihydrocarvone, also known as (2r,5r)-2-methyl-5-isopropenylcyclohexanone, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids 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. Thus, (1r,4r)-dihydrocarvone is considered to be an isoprenoid lipid molecule (1r,4r)-dihydrocarvone is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (1r,4r)-dihydrocarvone is a herbal and minty tasting compound found in spearmint, which makes (1r,4r)-dihydrocarvone a potential biomarker for the consumption of this food product.
CAS Number5524-05-0
Structure
Thumb
Synonyms
SynonymSource
(2R,5R)-2-Methyl-5-isopropenylcyclohexanoneChEBI
(2R,5R)-5-Isopropenyl-2-methylcyclohexanoneChEBI
(2R-trans)-2-Methyl-5-(1-methylvinyl)cyclohexan-1-oneChEBI
D-DihydrocarvoneChEBI
(+)-Dihydrocarvonemanual
(+)-trans-Dihydrocarvonemanual
(1R,4R)-(+)-Dihydrocarvonemanual
(1R,4R)-Dihydrocarvonebiospider
(1R,4R)-p-menth-8-en-2-onebiospider
(2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexanonebiospider
(2R,5R)-2-methyl-5-isopropenylcyclohexanonebiospider
(2R,5R)-5-isopropenyl-2-methylcyclohexanonebiospider
Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, (2R-trans)-manual
Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, (2R,5R)-biospider
D-dihydrocarvonebiospider
p-Menth-8-en-2-one, (+)- (8CI)manual
Predicted Properties
PropertyValueSource
Water Solubility0.56 g/LALOGPS
logP2.39ALOGPS
logP2.7ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.3 m³·mol⁻¹ChemAxon
Polarizability18.26 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H16O
IUPAC name(2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one
InChI IdentifierInChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-9H,1,4-6H2,2-3H3/t8-,9-/m1/s1
InChI KeyAZOCECCLWFDTAP-RKDXNWHRSA-N
Isomeric SMILESC[C@@H]1CC[C@H](CC1=O)C(C)=C
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
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
  • 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 stateNot Available
Physical DescriptionNot Available
Mass CompositionC 78.90%; H 10.59%; O 10.51%DFC
Melting PointNot Available
Boiling PointBp 221-222°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +17.5DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-8861ba576d835c24c4e2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-9700000000-7b7dfb5b5671e2efed19JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-100r-9000000000-02b93dd813cef6744911JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-3bdcde43911faafba8b7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-66279fba8a75e05ec84bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05n3-9500000000-02a124dc8509d82c4bb8JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-066r-9200000000-f04be1ac2888052faf10JSpectraViewer | MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC11398
Pubchem Compound ID22227
Pubchem Substance IDNot Available
ChEBI ID154
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJXJ77-S:JXJ78-T
EAFUS IDNot Available
Dr. Duke ID(+)-DIHYDROCARVONE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1106571
SuperScent IDNot Available
Wikipedia IDNot Available
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
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
minty
  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).