Record Information
Version1.0
Creation date2010-04-08 22:10:55 UTC
Update date2019-11-27 17:25:17 UTC
Primary IDFDB013800
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(-)-Menthone
DescriptionOccurs with menthol in many essential oils including peppermint and geranium oils. It 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. (-)-Menthone is found in many foods, some of which are ohelo berry, rocket salad, cauliflower, and common hazelnut.
CAS Number14073-97-3
Structure
Thumb
Synonyms
SynonymSource
(1S,4R)-MenthoneChEBI
(1S,4R)-p-Menthan-3-oneChEBI
(2R,5S)-2-Isopropyl-5-methylcyclohexanoneChEBI
(+)-(1S,4R)-MenthoneHMDB
(2R,5S)-5-Methyl-2-(propan-2-yl)cyclohexanoneHMDB
MenthoneMeSH
(+)-MenthoneHMDB
(2R,5S)-5-Methyl-2-(1-methylethyl)cyclohexanoneHMDB
D-MenthoneHMDB
(-)-(1R,4S)-Menthonebiospider
(-)-(2S,5R)-Menthonebiospider
(-)-5-Methyl-2-(1-methylethyl)cyclohexanonebiospider
(-)-Menthonedb_source
(1R,4S)-(-)-p-Menthan-3-onemanual
(1R,4S)-p-Menthan-3-onebiospider
(2S-trans)-5-Methyl-2-(1-methylethyl)cyclohexanonebiospider
(2S, 5R)-trans-2-Isopropyl-5-methylcyclohexanoneHMDB
(2S,5R)-2-Isopropyl-5-methylcyclohexanonebiospider
(2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexanonebiospider
(2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexanonebiospider
(2S,5R)-MenthoneChEBI
(2S,5R)-trans-2-Isopropyl-5-methylcyclohexanonemanual
5-Methyl-2-(1-methylethyl)-(2S-trans)-cyclohexanoneHMDB
5-Methyl-2-(1-methylethyl)-(2S,5R)-cyclohexanoneHMDB
Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2S-trans)-biospider
Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2S,5R)-biospider
L-Menthonemanual
Predicted Properties
PropertyValueSource
logP3.05ChemAxon
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
Polarizability18.94 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H18O
IUPAC name(2R,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
InChI KeyNFLGAXVYCFJBMK-UHFFFAOYSA-N
Isomeric SMILESCC(C)C1CCC(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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 77.87%; H 11.76%; O 10.37%DFC
Melting PointMp -6°DFC
Boiling PointBp 207°DFC
Experimental Water Solubility0.497 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP3.05GRIFFIN,S ET AL. (1999)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -24.8DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive Indexn23D 1.4490DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06r7-9300000000-1d150f2cf0a23dbfef0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-fa99f8c083212e4f2fc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-9800000000-7bf975ea31bcef83aa61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9000000000-3f8923896797c4486693View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-d55afdef2faae68197a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-91ec697d11dad181a342View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01oy-9600000000-7933610ac6051fc8ef81View in MoNA
ChemSpider ID24636
ChEMBL IDCHEMBL276311
KEGG Compound IDC00843
Pubchem Compound ID26447
Pubchem Substance IDNot Available
ChEBI ID15410
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35162
CRC / DFC (Dictionary of Food Compounds) IDJHQ37-H:JHL57-O
EAFUS IDNot Available
Dr. Duke ID(-)-MENTHONE
BIGG IDNot Available
KNApSAcK IDC00000811
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1008131
SuperScent ID26447
Wikipedia IDMenthone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti acetylcholinesterase38462 An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
raspberry
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
camphoraceous
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
deep
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
menthol
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
peppermint
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
camphor
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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).