Record Information
Version1.0
Creation date2010-04-08 22:08:30 UTC
Update date2018-01-25 19:39:45 UTC
Primary IDFDB009286
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namecis-Dihydrocarvone
DescriptionCis-dihydrocarvone, also known as (2r,5s)-2-methyl-5-isopropenylcyclohexanone or (1r,4s)-menth-8-en-2-one, 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, cis-dihydrocarvone is considered to be an isoprenoid lipid molecule. Cis-dihydrocarvone is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Cis-dihydrocarvone is a herbal and warm tasting compound and can be found in a number of food items such as dill, spearmint, wild celery, and common oregano, which makes cis-dihydrocarvone a potential biomarker for the consumption of these food products.
CAS Number3792-53-8
Structure
Thumb
Synonyms
SynonymSource
(1R,4S)-Iso-dihydrocarvoneChEBI
(1R,4S)-IsodihydrocarvoneChEBI
(2R,5S)-2-Methyl-5-isopropenylcyclohexanoneChEBI
(2R,5S)-5-Isopropenyl-2-methylcyclohexanoneChEBI
(+/-)-Isodihydrocarvonemanual
(z)-dihydrocarvonebiospider
(z)-isodihydrocarvonebiospider
cis-p-Menth-8-en-2-onemanual
Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, (2R,5S)-rel-manual
Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, cis-manual
Isodihydrocarvonemanual
p-Menth-8-en-2-one, cis-manual
p-Menth-8-en-2-one, Z-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
Polarizability17.9 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H16O
IUPAC name(2R,5S)-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-BDAKNGLRSA-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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-aac90d2e594a64ffc23bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-9600000000-07ad24338c7e47056fd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0le9-9000000000-a10b5ec9782fd22e6d6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-9820037a1b10b33bdc1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-ab126e3fddd65ad137c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mx-9500000000-380342ffa7a1fd0a2134View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID443167
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS ID911
Dr. Duke ID(Z)-DIHYDROCARVONE|CIS-DIHYDROCARVONE|ISODIHYDROCARVONE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet ID3792-53-8
GoodScent IDrw1416651
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
herb
  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
warm
  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. 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).