Showing Compound (-)-Menthol (FDB014499)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:18 UTC

Update date

2019-11-26 03:10:11 UTC

Primary ID

FDB014499

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(-)-Menthol

Description

Menthol, 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 Number

2216-51-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(-)-(1R,3R,4S)-Menthol	ChEBI
(1alpha,2beta,5alpha)-5-Methyl-2(1-methylethyl)cyclohexanol	ChEBI
(1R,3R,4S)-(-)-Menthol	ChEBI
(1R-(1-alpha,2-beta,5-alpha))-5-Methyl-2-(1-methylethyl)cyclohexanol	ChEBI
L-Menthol	ChEBI
Levomenthol	ChEBI
Levomentholum	ChEBI
Levomentol	ChEBI
(1a,2b,5a)-5-Methyl-2(1-methylethyl)cyclohexanol	Generator
(1Α,2β,5α)-5-methyl-2(1-methylethyl)cyclohexanol	Generator
(1R-(1-a,2-b,5-a))-5-Methyl-2-(1-methylethyl)cyclohexanol	Generator
(1R-(1-Α,2-β,5-α))-5-methyl-2-(1-methylethyl)cyclohexanol	Generator
(-)-Menthyl alcohol	HMDB
(-)-trans-p-Menthan-cis-ol	HMDB
(1R)-(-)-Menthol	HMDB
(1R,2S,5R)-(-)-Menthol	HMDB
(R)-(-)-Menthol	HMDB
1-Menthol	HMDB
2-Isopropyl-5-methylcyclohexanol	HMDB
5-Methyl-2-(1-methylethyl)cyclohexanol	HMDB
5-Methyl-2-propan-2-ylcyclohexan-1-ol	HMDB
D-(-)-Menthol	HMDB
Hexahydrothymol	HMDB
L-(-)-Menthol	HMDB
Menthacamphor	HMDB
Menthomenthol	HMDB
p-Menthan-3-ol	HMDB
Peppermint camphor	HMDB
U.S.p. menthol	HMDB
Kerasal	HMDB
Menthol, (1alpha,2beta,5alpha)-isomer	HMDB
Menthol	MeSH
(-)-Menthol	db_source
(-)-menthyl alcohol	biospider
(-)-trans-p-menthan-cis-ol	biospider
(1alpha,2beta,5alpha)-5-methyl-2(1-methylethyl)cyclohexanol	biospider
(1R-(1-α,2-β,5-α))-5-methyl-2-(1-methylethyl)cyclohexanol	Generator
(1R,2S,5R)-2-isopropyl-5-methylcyclohexanol	biospider
(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexanol	biospider
(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol	biospider
(1R,2S,5R)-5-methyl-2-propan-2-yl-cyclohexan-1-ol	biospider
(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol	biospider
(1R,3R,4S)-(-)-MENTHOL	biospider
(1α,2β,5α)-5-methyl-2(1-methylethyl)cyclohexanol	Generator
Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-	biospider
Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,3R,4S)-	biospider
FEMA 2665	db_source
L-(-)-menthol	biospider
L-menthol	biospider
Menthol, (1R,3R,4S)-(-)-	biospider
Menthol, l-	biospider
P-Menthan-3-ol	HMDB

Predicted Properties

Property	Value	Source
Water Solubility	0.56 g/L	ALOGPS
logP	2.68	ALOGPS
logP	2.66	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	19.55	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.45 m³·mol⁻¹	ChemAxon
Polarizability	19.69 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H20O

IUPAC name

(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol

InChI Identifier

InChI=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 Key

NOOLISFMXDJSKH-KXUCPTDWSA-N

Isomeric SMILES

CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O

Average Molecular Weight

156.269

Monoisotopic Molecular Weight

156.151415264

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane 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 Framework

Aliphatic homomonocyclic compounds

External Descriptors

p-menthan-3-ol (CHEBI:15409 )
Menthane monoterpenoids (C00400 )
Cyclic monoterpenes (C00400 )
Menthane monoterpenoids (LMPR0102090001 )

Ontology

Physiological effect

Health effect:

Health condition:

Coma

Ear and labyrinth disorders:

Vertigo

Gastrointestinal disorders:

Vomiting

General disorders and administration site conditions:

Pain

Ingestion

Source:

Food

Synthetic:

Personal care product

Environmental:

Tobacco smoke

Biological:

Plant:

Biological location:

Tissue and substructures:

Organ and components:

Cell and elements:

Extracellular

Cell:

Nerve cell

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Industrial application:

Pharmaceutical industry:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 76.86%; H 12.90%; O 10.24%	DFC
Melting Point	Mp 42.5-43°	DFC
Boiling Point	Bp 216°	DFC
Experimental Water Solubility	0.49 mg/mL at 25 oC	CHEMICALS INSPECTION AND TESTING INSTITU (1992)
Experimental logP	3.40	GRIFFIN,S ET AL. (1999)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]20D -50 (c, 2 in CHCl3)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-00ea-9100000000-602436010653202a4da9	Spectrum
GC-MS	(-)-Menthol, 1 TMS, GC-MS Spectrum	splash10-0006-1900000000-cc06fe70d7649d059f92	Spectrum
GC-MS	(-)-Menthol, non-derivatized, GC-MS Spectrum	splash10-00ea-9100000000-0be605183591bf5f33a0	Spectrum
GC-MS	(-)-Menthol, non-derivatized, GC-MS Spectrum	splash10-00ea-9100000000-977cf0c036d597693beb	Spectrum
GC-MS	(-)-Menthol, non-derivatized, GC-MS Spectrum	splash10-0006-1900000000-cc06fe70d7649d059f92	Spectrum
GC-MS	(-)-Menthol, non-derivatized, GC-MS Spectrum	splash10-00ym-9100000000-ff2f7ebe48769147a112	Spectrum
Predicted GC-MS	(-)-Menthol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4l-9600000000-fcf4b2a96455b111f889	Spectrum
Predicted GC-MS	(-)-Menthol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01w0-9520000000-26cc8cab97979ec9fb4d	Spectrum
Predicted GC-MS	(-)-Menthol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(-)-Menthol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-053r-9300000000-d9c35833e73c8655fb23	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0ldl-9000000000-abf2f837df49fbedc53c	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0007-9000000000-adee6385265c6606326d	Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive	splash10-00ea-9100000000-e3f1b7b69a021063fabb	Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-DX-300) , Positive	splash10-00ea-9100000000-d69777874c9615b7e751	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0900000000-39d327015211bdc2b4e8	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-6900000000-67e6c41c2a8d759d6caf	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aor-9200000000-88888989ba15a9dc0269	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-3a700dc611fb070e6b45	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-86ed17c709dc4636ad41	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bti-6900000000-fc116bf41f068d3f6f75	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05mk-9800000000-bb8a9e58bdc61e2654e6	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-053e-9100000000-6405f7fe35f6f6bdc8c5	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-fee5c7d55bf523973cbf	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-f6034c6a8245c68a37ac	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-7efa42d43b7858e2c2ce	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zfr-0900000000-b6eef0a7f66ac7e97e78	Spectrum

NMR

Type	Description	View
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

15409

Phenol-Explorer ID

Not Available

DrugBank ID

DB00825

HMDB ID

HMDB03352

CRC / DFC (Dictionary of Food Compounds) ID

JRL74-J:JRL66-I

EAFUS ID

2144

Dr. Duke ID

L-MENTHOL|MENTHOL|(-)-MENTHOL

BIGG ID

Not Available

KNApSAcK ID

C00000810

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

GoodScent ID

SuperScent ID

Wikipedia ID

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
analgesic	35480	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
anesthetic			DUKE
anti acetylcholinesterase	38462	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 aggregant			DUKE
anti allergic	50857	A drug used to treat allergic reactions.	DUKE
anti asthmatic	49167	A drug used to treat asthma.	DUKE
anti bacillus	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti bronchitic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti dandruff			DUKE
anti escherichic			DUKE
anti halitosic			DUKE
anti histaminic	37956	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 inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti listeria	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti neuralgic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti odontalgic			DUKE
anti pruritic	50177	A drug used to treat or prevent skin disorders or for the routine care of skin.	DUKE
anti pyretic	35493	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 rheumatic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti salmonella	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti sinusitic			DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti staphylococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti streptococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti tartar			DUKE
anti vaginitic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti vulvitic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
bradycardic	38070	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
bronchomucolytic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
bronchomucotropic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
bronchorrheic			DUKE
calcium antagonist	48706	Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.	DUKE
candidicide			DUKE
carminative			DUKE
choleretic			DUKE
ciliotoxic			DUKE
central nervous system depressant	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
central nervous system stimulant	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
congestant			DUKE
convulsant			DUKE
counterirritant			DUKE
decongestant	77715	A drug used to relieve nasal congestion in the upper respiratory tract.	DUKE
dermatitigenic			DUKE
diaphoretic			DUKE
enterorelaxant			DUKE
expectorant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
gastrosedative	55324	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
irritant			DUKE
myorelaxant			DUKE
nematicide	25491	A substance used to destroy pests of the phylum Nematoda (roundworms).	DUKE
neurodepressant			DUKE
neuropathogenic			DUKE
nociceptive			DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
refrigerant	78433	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
rubefacient			DUKE
termiticide			DUKE
transdermal			DUKE
vibriocide			DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
peppermint	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 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
camphoraceous	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
tobacco	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
cooling	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
mentholic	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
minty	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.