You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB01741
NameMenthone
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description(-)-Menthone, also known as L-menthone or p-menthan-3-one, 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. Thus, (-)-menthone is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on (-)-Menthone.
Structure
Thumb
Synonyms
  • (-)-Menthone
  • (2R,5S)-rel-5-methyl-2-(1-methylethyl)cyclohexanone
  • l-Menthone
  • menthone
  • p-Menthan-3-one
  • rel-(1R,4S)-p-menthan-3-one
  • rel-(2R,5S)-2-isopropyl-5-methylcyclohexanone
  • trans-5-methyl-2-(1-methylethyl)cyclohexanone
  • trans-menthan-3-one
  • trans-menthone
  • trans-p-menthan-3-one
  • (1R,4S)-Menthone
  • (1R,4S)-p-Menthan-3-one
  • (2S,5R)-2-Isopropyl-5-methylcyclohexanone
  • (2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexanone
  • (2S-trans)-5-Methyl-2-(1-methylethyl)cyclohexanone
  • (2S,5R)-Menthone
  • (-)-(1R,4S)-Menthone
  • (-)-(2S,5R)-Menthone
  • (-)-5-Methyl-2-(1-methylethyl)cyclohexanone
  • (1R,4S)-(-)-P-Menthan-3-one
  • (2S, 5R)-trans-2-Isopropyl-5-methylcyclohexanone
  • (2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexanone
  • 5-Methyl-2-(1-methylethyl)-(2S,5R)-cyclohexanone
  • 5-Methyl-2-(1-methylethyl)-(2S-trans)-cyclohexanone
  • (1R,4S)-p-Menth-3-one
  • (2S,5R)-(-)-Menthone
  • (2S,5R)-2-Isopropyl-5-methylcyclohexan-1-one
  • trans-(-)-p-Menthan-3-one
CAS number89-80-5
WeightAverage: 154.2493
Monoisotopic: 154.135765198
InChI KeyNFLGAXVYCFJBMK-BDAKNGLRSA-N
InChIInChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9+/m1/s1
IUPAC Name(2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-one
Traditional IUPAC Name(-)-menthone
Chemical FormulaC10H18O
SMILESCC(C)[C@@H]1CC[C@@H](C)CC1=O
Chemical Taxonomy
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
Physical Properties
StateLiquid
Charge0
Melting point−6 °C
Experimental Properties
PropertyValueReference
Water Solubility0.688 mg/mL at 25 oC [SUZUKI,T (1991)]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.26 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
Polarizability19.02 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
FreshFDB009778
GreenFDB009778
MintyFDB009778
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-7900000000-72f9ad70ae1001e21eafJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004j-2900000000-9f3548951fa6e98aa410JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0170-4900000000-82f88e79cd91a887a98fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-7900000000-72f9ad70ae1001e21eafJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004j-2900000000-9f3548951fa6e98aa410JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0170-4900000000-82f88e79cd91a887a98fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-07bo-9300000000-3f63fc6dbb3efa362d59JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-07bo-9300000000-3f63fc6dbb3efa362d59JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052g-9300000000-f26613921d7b53d7fd71JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-9000000000-6701bba716a6affa8766JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-0002-9000000000-b0b5dd86e6d1a6de2171JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-000t-9000000000-d18a7464317ee5b6d7ccJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-000i-1900000000-244db80c070c100b12b8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-000i-2900000000-b84cff8176943c1c01cfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-000i-4900000000-3164f9befc45e23067a9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-000i-7900000000-aa7dd74302c4ed215ce5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-001a-9600000000-f847c953bdb697e434a9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0012-9400000000-23a0fccfb9523e3d21ecJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000t-9200000000-54afdeb4f58eddee2447JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000t-9100000000-b0e554c807437d6fbe0aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-000t-9000000000-575fad481c43a10742f2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-00l2-9000000000-2869717ccfb0fbe67a4bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-015a-9000000000-b2a684427d58a3d1e8d8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-0690-9000000000-68fcde55699d18a522f7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-0ar3-9100000000-25c9da89880a6d44b24dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-000t-9000000000-96ef6ca330f562128056JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-9000000000-70388bb385562f798a7aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0a4i-1900000000-05762909cf77edb47697JSpectraViewer | MoNA
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
MSMass Spectrum (Electron Ionization)splash10-07bf-9300000000-03e6f833d8a9130c9648JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID36503
HMDB IDHMDB0035162
Pubchem Compound ID26447
Kegg IDC00843
ChemSpider ID24210726
FOODB IDFDB009778
Wikipedia IDNot Available
BioCyc IDNot Available