FComEx: (-)-Menthol (PC000714)

Record Information

Version

1.0

Creation date

2015-10-09 22:32:10 UTC

Update date

2017-01-19 02:36:33 UTC

FoodComEx ID

PC000714

FoodDB Record

FDB014499

Chemical Information

Name

(-)-Menthol

Description

Present in large amts. in peppermint oil (Mentha piperita), also in other Mentha subspecies. It is used in confectionery and perfumery. Flavouring agent (-)-menthol is the major occuring menthol stereoisomer in nature. (-)-Menthol is found in many foods, some of which are lovage, sweet basil, sweet marjoram, and orange mint.

CAS Number

2216-51-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

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

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

Chemical Taxonomy

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 )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	3.40	GRIFFIN,S ET AL. (1999)
Experimental Water Solubility	0.49 mg/mL at 25 oC	CHEMICALS INSPECTION AND TESTING INSTITU (1992)
Melting Point	Mp 42.5-43°	DFC

Foods of Origin