Record Information
Version1.0
Creation date2010-04-08 22:11:23 UTC
Update date2019-11-26 03:10:31 UTC
Primary IDFDB014639
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(-)-Isomenthone
DescriptionIsomenthone, also known as alpha-isomenthone or cis-p-menthone, 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. Isomenthone is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number1196-31-2
Structure
Thumb
Synonyms
SynonymSource
(1S,4S)-(-)-p-Menthan-3-oneChEBI
(1S,4S)-p-Menthan-3-oneChEBI
(2S,5S)-2-Isopropyl-5-methylcyclohexanoneChEBI
(2S-cis)-5-Methyl-2-(1-methylethyl)cyclohexanoneChEBI
L-IsomenthoneChEBI
(1R,4R)-(+)-p-Menthan-3-oneHMDB
(1R,4R)-p-Menthan-3-oneHMDB
(-)-IsomenthoneHMDB
(1S,4S)-IsomenthoneHMDB
(2S,5S)-2-Isopropyl-5-methylcyclohexan-1-oneHMDB
(2S,5S)-5-Methyl-2-(1-methylethyl)cyclohexanoneHMDB
alpha-IsomenthoneHMDB
cis-MenthoneHMDB
cis-p-Menthan-3-oneHMDB
cis-p-MenthoneHMDB
DL-IsomenthoneHMDB
Α-isomenthoneHMDB
IsomenthoneMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.27 g/LALOGPS
logP2.65ALOGPS
logP3.05ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.52 m³·mol⁻¹ChemAxon
Polarizability18.67 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H18O
IUPAC name(2S,5S)-5-methyl-2-(propan-2-yl)cyclohexan-1-one
InChI IdentifierInChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9-/m0/s1
InChI KeyNFLGAXVYCFJBMK-IUCAKERBSA-N
Isomeric SMILESCC(C)[C@@H]1CC[C@H](C)CC1=O
Average Molecular Weight154.2493
Monoisotopic Molecular Weight154.135765198
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 77.87%; H 11.76%; O 10.37%DFC
Melting PointNot Available
Boiling PointBp7 79-80°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -94.3DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06r7-9300000000-1d150f2cf0a23dbfef0bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-fa99f8c083212e4f2fc3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-9800000000-7bf975ea31bcef83aa61JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9000000000-3f8923896797c4486693JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-d55afdef2faae68197a6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-91ec697d11dad181a342JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01oy-9600000000-7933610ac6051fc8ef81JSpectraViewer
ChemSpider ID4937714
ChEMBL IDNot Available
KEGG Compound IDC17125
Pubchem Compound ID6432469
Pubchem Substance IDNot Available
ChEBI ID36496
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34972
CRC / DFC (Dictionary of Food Compounds) IDJHQ37-H:JTF43-J
EAFUS IDNot Available
Dr. Duke ID(-)-ISOMENTHONE
BIGG IDNot Available
KNApSAcK IDC00010904
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1507821
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
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— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).