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Record Information
Version3.6
Creation Date2012-09-11 20:06:32 UTC
Update Date2017-08-15 22:23:47 UTC
HMDB IDHMDB0035162
Secondary Accession Numbers
  • HMDB35162
Metabolite Identification
Common Name(-)-Menthone
Description(-)-Menthone is found in cornmint. (-)-Menthone occurs with menthol in many essential oils including peppermint and geranium oils. (-)-Menthone is used in flavour compositions.L-Menthone is the most abundant in nature of the four possible stereoisomers. Menthone is used in perfumery and cosmetics for its characteristic aromatic and minty odor. (Wikipedia) (-)-Menthone belongs to the family of p-Menthane Monoterpenes. These are monoterpenes whose structure is based on the p-menthane backbone.
Structure
Thumb
Synonyms
ValueSource
(1R,4S)-P-Menthan-3-oneChEBI
(2S,5R)-2-Isopropyl-5-methylcyclohexanoneChEBI
(2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexanoneChEBI
(2S,5R)-MenthoneChEBI
(2S-trans)-5-Methyl-2-(1-methylethyl)cyclohexanoneChEBI
L-MenthoneChEBI
P-Menthan-3-oneChEBI
(-)-(1R,4S)-MenthoneHMDB
(-)-(2S,5R)-MenthoneHMDB
(-)-5-Methyl-2-(1-methylethyl)cyclohexanoneHMDB
(1R,4S)-(-)-P-Menthan-3-oneHMDB
(2S, 5R)-trans-2-Isopropyl-5-methylcyclohexanoneHMDB
(2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexanoneHMDB
5-Methyl-2-(1-methylethyl)-(2S,5R)-cyclohexanoneHMDB
5-Methyl-2-(1-methylethyl)-(2S-trans)-cyclohexanoneHMDB
Chemical FormulaC10H18O
Average Molecular Weight154.253
Monoisotopic Molecular Weight154.1357652
IUPAC Name(2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-one
Traditional Name(-)-menthone
CAS Registry Number14073-97-3
SMILES
CC(C)[C@@H]1CC[C@@H](C)CC1=O
InChI Identifier
InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9+/m1/s1
InChI KeyNFLGAXVYCFJBMK-BDAKNGLRSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Cyclohexanone
  • Cyclic ketone
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrient
Application
  • Nutrient
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-6 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.497 mg/mL at 25 °CNot Available
LogP3.05Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.27 mg/mLALOGPS
logP2.65ALOGPS
logP3.05ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.52 m3·mol-1ChemAxon
Polarizability19.02 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - EI-Bsplash10-03di-7900000000-72f9ad70ae1001e21eafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB013800
KNApSAcK IDC00000811
Chemspider ID24636
KEGG Compound IDC00843
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMenthone
NuGOwiki LinkHMDB0035162
METLIN IDNot Available
PubChem Compound26447
PDB IDNot Available
ChEBI ID15410
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .