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trans-Dihydrocarvone (FDB003876)

Record Information
Version1.0
Creation date2010-04-08 22:05:59 UTC
Update date2019-11-26 02:59:39 UTC
Primary IDFDB003876
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nametrans-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 Number5948-04-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-066r-9200000000-f04be1ac2888052faf102015-03-01View Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-8861ba576d835c24c4e22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-9700000000-7b7dfb5b5671e2efed192016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-100r-9000000000-02b93dd813cef67449112016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-3bdcde43911faafba8b72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-66279fba8a75e05ec84b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05n3-9500000000-02a124dc8509d82c4bb82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gws-7900000000-b08efab8959a09a262162021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-9200000000-13ccbe770389182b9c062021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-4b6afc70d0efd7f97f152021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-c373c9eea3cebf186f532021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-6d20364e296745592a692021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kn-6900000000-23186e60d8ffad6745272021-10-21View Spectrum
NMR
TypeDescriptionView
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
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 IDNot Available
Dr. Duke ID(E)-DIHYDROCARVONE|TRANS-DIHYDROCARVONE
BIGG IDNot Available
KNApSAcK IDC00033439
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID5948-04-9
GoodScent IDrw1511171
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
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.
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
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.