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Record Information
Version1.0
Created at2012-09-11 20:06:32 UTC
Updated at2021-08-19 23:58:13 UTC
NP-MRD IDNP0000571
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-Menthone
Description(-)-Menthone, also known as (1R,4S)-menthone or L-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. (-)-Menthone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, (-)-menthone is considered to be an isoprenoid lipid molecule.
Structure
Thumb
Synonyms
ValueSource
(1R,4S)-MenthoneChEBI
(1R,4S)-p-Menthan-3-oneChEBI
(2S,5R)-2-Isopropyl-5-methylcyclohexanoneChEBI
(2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexanoneChEBI
(2S-trans)-5-Methyl-2-(1-methylethyl)cyclohexanoneChEBI
L-MenthoneChEBI
p-Menthan-3-oneChEBI
(2S,5R)-MenthoneHMDB
(-)-(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
MenthoneHMDB
(1R,4S)-p-Menth-3-oneHMDB
(2S,5R)-(-)-MenthoneHMDB
(2S,5R)-2-Isopropyl-5-methylcyclohexan-1-oneHMDB
trans-(-)-p-Menthan-3-oneHMDB
(-)-MenthoneHMDB
Chemical FormulaC10H18O
Average Mass154.2530 Da
Monoisotopic Mass154.13577 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Cannabis sativaCannabisDB
      Not Available
Clinopodium serpyllifoliumLOTUS Database
Hedeoma pulegioidesPlant
Laurencia dendroidea-
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha gattefosseKNApSAcK Database
Mentha piperitaLOTUS Database
Mentha piperita L.KNApSAcK Database
Mentha pulegiumLOTUS Database
Mentha spicataFooDB
Mentha spp.KNApSAcK Database
Mentha x piperitaFooDB
Mentha x piperita L.KNApSAcK Database
Minthostachys mollisLOTUS Database
Pelargonium tomentosumPlant
Pinus palustrisKNApSAcK Database
Schizonepeta tenuifoliaLOTUS Database
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
Experimental Properties
PropertyValueReference
Melting Point-6 °CNot Available
Boiling Point207.00 to 210.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.5 mg/mL at 25 °CNot Available
LogP3.05Not Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035162
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB009778
KNApSAcK IDC00000811
Chemspider ID24636
KEGG Compound IDC00843
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound26447
PDB IDNot Available
ChEBI ID15410
Good Scents IDrw1008131
References
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Rong MK, Bobylev EO, Holtrop F, Nieger M, Ehlers AW, Slootweg JC, Lammertsma K: Atypical And Asymmetric 1,3-P,N-Ligands: The Synthesis, Coordination and Catalytic Performance of Cycloiminophosphanes. Chemistry. 2021 Aug 17. doi: 10.1002/chem.202101921. [PubMed:34403555 ]
  6. Sumida R, Tanaka Y, Niki K, Sei Y, Toyota S, Yoshizawa M: Cyclic monoterpenes trapped in a polyaromatic capsule: unusual selectivity, isomerization, and volatility suppression. Chem Sci. 2021 May 18;12(29):9946-9951. doi: 10.1039/d1sc01987b. eCollection 2021 Jul 28. [PubMed:34377391 ]
  7. Ueda T, Murata M, Yokawa K: Single Wavelengths of LED Light Supplement Promote the Biosynthesis of Major Cyclic Monoterpenes in Japanese Mint. Plants (Basel). 2021 Jul 12;10(7). pii: plants10071420. doi: 10.3390/plants10071420. [PubMed:34371623 ]
  8. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.