Record Information
Version1.0
Creation date2010-04-08 22:11:18 UTC
Update date2019-11-26 03:10:11 UTC
Primary IDFDB014499
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 Number2216-51-5
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
(-)-Mentholdb_source
(-)-menthyl alcoholbiospider
(-)-trans-p-menthan-cis-olbiospider
(1alpha,2beta,5alpha)-5-methyl-2(1-methylethyl)cyclohexanolbiospider
(1R-(1-α,2-β,5-α))-5-methyl-2-(1-methylethyl)cyclohexanolGenerator
(1R,2S,5R)-2-isopropyl-5-methylcyclohexanolbiospider
(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexanolbiospider
(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-olbiospider
(1R,2S,5R)-5-methyl-2-propan-2-yl-cyclohexan-1-olbiospider
(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-olbiospider
(1R,3R,4S)-(-)-MENTHOLbiospider
(1α,2β,5α)-5-methyl-2(1-methylethyl)cyclohexanolGenerator
Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-biospider
Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,3R,4S)-biospider
FEMA 2665db_source
L-(-)-mentholbiospider
L-mentholbiospider
Menthol, (1R,3R,4S)-(-)-biospider
Menthol, l-biospider
P-Menthan-3-olHMDB
Predicted PropertiesNot Available
Chemical FormulaC10H20O
IUPAC name
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 76.86%; H 12.90%; O 10.24%DFC
Melting PointMp 42.5-43°DFC
Boiling PointBp 216°DFC
Experimental Water Solubility0.49 mg/mL at 25 oCCHEMICALS INSPECTION AND TESTING INSTITU (1992)
Experimental logP3.40GRIFFIN,S ET AL. (1999)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -50 (c, 2 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MSNot Available
NMRNot Available
ChemSpider ID15803
ChEMBL IDCHEMBL470670
KEGG Compound IDC00400
Pubchem Compound ID16666
Pubchem Substance IDNot Available
ChEBI ID15409
Phenol-Explorer IDNot Available
DrugBank IDDB00825
HMDB IDHMDB03352
CRC / DFC (Dictionary of Food Compounds) IDJRL74-J:JRL66-I
EAFUS ID2144
Dr. Duke IDL-MENTHOL|MENTHOL|(-)-MENTHOL
BIGG IDNot Available
KNApSAcK IDC00000810
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID2216-51-5
GoodScent IDrw1030471
SuperScent ID16666
Wikipedia IDMenthol
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
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
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
anestheticDUKE
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 asthmatic49167 A drug used to treat asthma.DUKE
anti bacillus33282 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 bronchitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti dandruffDUKE
anti escherichicDUKE
anti halitosicDUKE
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 inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti listeria33282 A substance that kills or slows the growth of bacteria.DUKE
anti neuralgic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti odontalgicDUKE
anti pruritic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti pyretic35493 A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.DUKE
anti rheumatic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.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 sinusiticDUKE
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
anti streptococcic33282 A substance that kills or slows the growth of bacteria.DUKE
anti tartarDUKE
anti vaginitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti vulvitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
bradycardic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
bronchomucolytic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
bronchomucotropic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
bronchorrheicDUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
candidicideDUKE
carminativeDUKE
cholereticDUKE
ciliotoxicDUKE
central nervous system depressant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
central nervous system stimulant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
congestantDUKE
convulsantDUKE
counterirritantDUKE
decongestant77715 A drug used to relieve nasal congestion in the upper respiratory tract.DUKE
dermatitigenicDUKE
diaphoreticDUKE
enterorelaxantDUKE
expectorant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
gastrosedative55324 A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion.DUKE
irritantDUKE
myorelaxantDUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
neurodepressantDUKE
neuropathogenicDUKE
nociceptiveDUKE
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
refrigerant78433 A substance used in a thermodynamic heat pump cycle or refrigeration cycle that undergoes a phase change from a gas to a liquid and back. Refrigerants are used in air-conditioning systems and freezers or refrigerators and are assigned a "R" number (by ASHRAE - formerly the American Society of Heating, Refrigerating and Air Conditioning Engineers), which is determined systematically according to their molecular structure.DUKE
rubefacientDUKE
termiticideDUKE
transdermalDUKE
vibriocideDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
peppermint
  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
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
camphoraceous
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
tobacco
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
cooling
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
mentholic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
minty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.