Record Information
Version1.0
Creation date2010-04-08 22:11:51 UTC
Update date2015-07-20 23:18:29 UTC
Primary IDFDB015462
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(±)-Menthol
DescriptionMenthol, also known as levomenthol or hexahydrothymol, 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, menthol is considered to be an isoprenoid lipid molecule. Menthol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Menthol is a potentially toxic compound.
CAS Number15356-20-4
Structure
Thumb
Synonyms
SynonymSource
(-)-(1R,3R,4S)-MentholChEBI
(1alpha,2beta,5alpha)-5-Methyl-2(1-methylethyl)cyclohexanolChEBI
(1R,3R,4S)-(-)-MentholChEBI
(1R-(1-alpha,2-beta,5-alpha))-5-Methyl-2-(1-methylethyl)cyclohexanolChEBI
L-MentholChEBI
LevomentholChEBI
LevomentholumChEBI
LevomentolChEBI
(1a,2b,5a)-5-Methyl-2(1-methylethyl)cyclohexanolGenerator
(1Α,2β,5α)-5-methyl-2(1-methylethyl)cyclohexanolGenerator
(1R-(1-a,2-b,5-a))-5-Methyl-2-(1-methylethyl)cyclohexanolGenerator
(1R-(1-Α,2-β,5-α))-5-methyl-2-(1-methylethyl)cyclohexanolGenerator
(-)-Menthyl alcoholHMDB
(-)-trans-p-Menthan-cis-olHMDB
(1R)-(-)-MentholHMDB
(1R,2S,5R)-(-)-MentholHMDB
(R)-(-)-MentholHMDB
1-MentholHMDB
2-Isopropyl-5-methylcyclohexanolHMDB
5-Methyl-2-(1-methylethyl)cyclohexanolHMDB
5-Methyl-2-propan-2-ylcyclohexan-1-olHMDB
D-(-)-MentholHMDB
HexahydrothymolHMDB
L-(-)-MentholHMDB
MenthacamphorHMDB
MenthomentholHMDB
p-Menthan-3-olHMDB
Peppermint camphorHMDB
U.S.p. mentholHMDB
KerasalHMDB
Menthol, (1alpha,2beta,5alpha)-isomerHMDB
MentholMeSH
(±)-Mentholbiospider
(+-)-Mentholbiospider
(+/-)-Mentholbiospider
(±)-Mentholdb_source
(DL)-5-Methyl-2-(1-methylethyl)cyclohexanolbiospider
cis-1 ,3-trans-1,4-(+-)-Mentholbiospider
cis-1,3-trans-1,4-(+-)-Mentholbiospider
DL-3-p-Menthanolbiospider
DL-Mentholbiospider
Menthol racemicbiospider
Menthol, (±)-biospider
Menthol, cis-1,3,trans-1,4-biospider
Menthol, cis-1,3,trans-1,4-(±)-biospider
Menthol, DL-biospider
Racementhol, BAN, INNdb_source
Racemic mentholbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.56 g/LALOGPS
logP2.68ALOGPS
logP2.66ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)19.55ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.45 m³·mol⁻¹ChemAxon
Polarizability19.69 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H20O
IUPAC name(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol
InChI IdentifierInChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10-/m1/s1
InChI KeyNOOLISFMXDJSKH-KXUCPTDWSA-N
Isomeric SMILESCC(C)[C@@H]1CC[C@@H](C)C[C@H]1O
Average Molecular Weight156.269
Monoisotopic Molecular Weight156.151415264
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
  • Cyclohexanol
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 76.86%; H 12.90%; O 10.24%DFC
Melting PointMp 34°DFC
Boiling PointBp 216°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00ea-9100000000-602436010653202a4da9Spectrum
GC-MS(-)-Menthol, 1 TMS, GC-MS Spectrumsplash10-0006-1900000000-cc06fe70d7649d059f92Spectrum
GC-MS(-)-Menthol, non-derivatized, GC-MS Spectrumsplash10-00ea-9100000000-0be605183591bf5f33a0Spectrum
GC-MS(-)-Menthol, non-derivatized, GC-MS Spectrumsplash10-00ea-9100000000-977cf0c036d597693bebSpectrum
GC-MS(-)-Menthol, non-derivatized, GC-MS Spectrumsplash10-0006-1900000000-cc06fe70d7649d059f92Spectrum
GC-MS(-)-Menthol, non-derivatized, GC-MS Spectrumsplash10-00ym-9100000000-ff2f7ebe48769147a112Spectrum
Predicted GC-MS(-)-Menthol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4l-9600000000-fcf4b2a96455b111f889Spectrum
Predicted GC-MS(-)-Menthol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01w0-9520000000-26cc8cab97979ec9fb4dSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-053r-9300000000-d9c35833e73c8655fb23Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0ldl-9000000000-abf2f837df49fbedc53cSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0007-9000000000-adee6385265c6606326dSpectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-00ea-9100000000-e3f1b7b69a021063fabbSpectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-DX-300) , Positivesplash10-00ea-9100000000-d69777874c9615b7e751Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0900000000-39d327015211bdc2b4e8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-6900000000-67e6c41c2a8d759d6cafSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9200000000-88888989ba15a9dc0269Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-3a700dc611fb070e6b45Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-86ed17c709dc4636ad41Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bti-6900000000-fc116bf41f068d3f6f75Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJRL74-J:KCK69-Q
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference