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Showing Compound (±)-Menthone (FDB009778)

Record Information
Version1.0
Creation date2010-04-08 22:08:47 UTC
Update date2020-09-17 15:41:34 UTC
Primary IDFDB009778
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. Thus, (-)-menthone is considered to be an isoprenoid lipid molecule (-)-Menthone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
CAS Number89-80-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(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
(±)-Menthonedb_source
(DL)-Menthonebiospider
Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2R,5S)-relmanual
DL-Menthonebiospider
DL-p-Menthan-3-onemanual
Neomenthonemanual
p-Menthonemanual
trans-Menthonemanual
trans-p-Menthonemanual
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
Polarizability19.02 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H18O
IUPAC name(2S,5R)-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+/m1/s1
InChI KeyNFLGAXVYCFJBMK-BDAKNGLRSA-N
Isomeric SMILESCC(C)[C@@H]1CC[C@@H](C)CC1=O
Average Molecular Weight154.253
Monoisotopic Molecular Weight154.1357652
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:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 PointBp10 82-83°DFC
Experimental Water Solubility0.688 mg/mL at 25 oCSUZUKI,T (1991)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive Indexn20D 1.4508DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-07bf-9300000000-03e6f833d8a9130c9648Spectrum
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-24fa3ff739ff064312abSpectrum
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-8900000000-5b42adf83e422cffefb6Spectrum
GC-MS(±)-Menthone, non-derivatized, GC-MS Spectrumsplash10-03di-7900000000-72f9ad70ae1001e21eafSpectrum
GC-MS(±)-Menthone, non-derivatized, GC-MS Spectrumsplash10-004j-2900000000-9f3548951fa6e98aa410Spectrum
GC-MS(±)-Menthone, non-derivatized, GC-MS Spectrumsplash10-0170-4900000000-82f88e79cd91a887a98fSpectrum
GC-MS(±)-Menthone, non-derivatized, GC-MS Spectrumsplash10-03di-7900000000-72f9ad70ae1001e21eafSpectrum
GC-MS(±)-Menthone, non-derivatized, GC-MS Spectrumsplash10-004j-2900000000-9f3548951fa6e98aa410Spectrum
GC-MS(±)-Menthone, non-derivatized, GC-MS Spectrumsplash10-0170-4900000000-82f88e79cd91a887a98fSpectrum
GC-MS(±)-Menthone, non-derivatized, GC-MS Spectrumsplash10-07bo-9300000000-3f63fc6dbb3efa362d59Spectrum
GC-MS(±)-Menthone, non-derivatized, GC-MS Spectrumsplash10-07bo-9300000000-3f63fc6dbb3efa362d59Spectrum
Predicted GC-MS(±)-Menthone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052g-9300000000-f26613921d7b53d7fd71Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-9000000000-6701bba716a6affa8766Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-0002-9000000000-b0b5dd86e6d1a6de2171Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-000t-9000000000-d18a7464317ee5b6d7ccSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-000i-1900000000-244db80c070c100b12b8Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-000i-2900000000-b84cff8176943c1c01cfSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-000i-4900000000-3164f9befc45e23067a9Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-000i-7900000000-aa7dd74302c4ed215ce5Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-001a-9600000000-f847c953bdb697e434a9Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0012-9400000000-23a0fccfb9523e3d21ecSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000t-9200000000-54afdeb4f58eddee2447Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000t-9100000000-b0e554c807437d6fbe0aSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-000t-9000000000-575fad481c43a10742f2Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-00l2-9000000000-2869717ccfb0fbe67a4bSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-015a-9000000000-b2a684427d58a3d1e8d8Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-0690-9000000000-68fcde55699d18a522f7Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-0ar3-9100000000-25c9da89880a6d44b24dSpectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-000t-9000000000-96ef6ca330f562128056Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-9000000000-70388bb385562f798a7aSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0a4i-1900000000-05762909cf77edb47697Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-fa99f8c083212e4f2fc3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-9800000000-7bf975ea31bcef83aa61Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9000000000-3f8923896797c4486693Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-d55afdef2faae68197a6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-91ec697d11dad181a342Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01oy-9600000000-7933610ac6051fc8ef81Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI ID36503
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJHQ37-H:LFY37-D
EAFUS ID2145
Dr. Duke IDMENTHONE|NEOMENTHONE
BIGG IDNot Available
KNApSAcK IDC00035341
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID89-80-5
GoodScent IDrw1398981
SuperScent IDNot Available
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
acaricide22153 A substance used to destroy pests of the subclass Acari (mites and ticks).DUKE
allelopathicDUKE
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
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
anti aggregantDUKE
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti bacillary33282 A substance that kills or slows the growth of bacteria.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti escherichicDUKE
anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
anti listeria33282 A substance that kills or slows the growth of bacteria.DUKE
anti salmonella33282 A substance that kills or slows the growth of bacteria.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti staphylococcic33282 A substance that kills or slows the growth of bacteria.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
candidicideDUKE
cerebrotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
culicideDUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
larvicideDUKE
mutagenicDUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
psychoactive35471 A loosely defined grouping of drugs that have effects on psychological function.DUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
trichomonicideDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
fresh
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
green
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).