CHEBI:15409 - (−)-menthol

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ChEBI Name (−)-menthol
ChEBI ID CHEBI:15409
ChEBI ASCII Name (-)-menthol
Definition A p-menthan-3-ol which has (1R,2S,5R)-stereochemistry. It is the most common naturally occurring enantiomer.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:101, CHEBI:10779, CHEBI:18493
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Formula C10H20O
Net Charge 0
Average Mass 156.26520
Monoisotopic Mass 156.151
InChI 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
InChIKey NOOLISFMXDJSKH-KXUCPTDWSA-N
SMILES CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O
Roles Classification
Biological Role(s): volatile oil component
Any metabolite that is found naturally as a component of a volatile oil.
(via p-menthan-3-ol )
Application(s): antitussive
An agent that suppresses cough. Antitussives have a central or a peripheral action on the cough reflex, or a combination of both. Compare with expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing, and mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration.
antispasmodic drug
A drug that suppresses spasms. These are usually caused by smooth muscle contraction, especially in tubular organs. The effect is to prevent spasms of the stomach, intestine or urinary bladder.
antipruritic drug
A drug, usually applied topically, that relieves pruritus (itching).
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ChEBI Ontology
Outgoing (−)-menthol (CHEBI:15409) has role antipruritic drug (CHEBI:59683)
(−)-menthol (CHEBI:15409) has role antispasmodic drug (CHEBI:53784)
(−)-menthol (CHEBI:15409) has role antitussive (CHEBI:51177)
(−)-menthol (CHEBI:15409) is a p-menthan-3-ol (CHEBI:25187)
(−)-menthol (CHEBI:15409) is enantiomer of (+)-menthol (CHEBI:76306)
Incoming (−)-menthyl β-D-glucoside (CHEBI:15411) has functional parent (−)-menthol (CHEBI:15409)
(±)-menthol (CHEBI:76310) has part (−)-menthol (CHEBI:15409)
(+)-menthol (CHEBI:76306) is enantiomer of (−)-menthol (CHEBI:15409)
IUPAC Name
(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol
INNs Sources
levomenthol ChemIDplus
lévomenthol WHO MedNet
levomentholum WHO MedNet
levomentol WHO MedNet
Synonyms Sources
(−)-(1R,3R,4S)-menthol ChemIDplus
(−)-menthol UniProt
(-)-Menthol KEGG COMPOUND
(1alpha,2beta,5alpha)-5-methyl-2(1-methylethyl)cyclohexanol ChEBI
(1R,3R,4S)-(−)-menthol NIST Chemistry WebBook
(1R-(1-α,2-β,5-α))-5-methyl-2-(1-methylethyl)cyclohexanol ChemIDplus
L-Menthol KEGG COMPOUND
l-menthol ChEBI
Database Links Databases
--MENTHOL MetaCyc
934 DrugCentral
C00000810 KNApSAcK
C00400 KEGG COMPOUND
CN101602651 Patent
D00064 KEGG DRUG
DB00825 DrugBank
HMDB03352 HMDB
LMPR0102090001 LIPID MAPS
Menthol Wikipedia
US2011313205 Patent
View more database links
Registry Numbers Types Sources
1902293 Reaxys Registry Number Reaxys
2216-51-5 CAS Registry Number KEGG COMPOUND
2216-51-5 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
17021997 PubMed citation Europe PMC
17498839 PubMed citation Europe PMC
18640225 PubMed citation Europe PMC
21353674 PubMed citation Europe PMC
22218824 PubMed citation Europe PMC
22348831 PubMed citation Europe PMC
23800946 PubMed citation Europe PMC
23963768 PubMed citation Europe PMC
7974298 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2011-02-02 (−)-Menthol is the main form of menthol occurring in nature, where it is commonly obtained from peppermint and other mint oils. Both it and its racemate (racementhol, prepared synthetically by hydrogenation of thymol) are used to rellieve minor throat irritaions. Menthol is also used as a topical analgesic to relieve minor aches and pains such as muscle cramps, sprains, headaches and similar conditions, while in perfumery, menthyl esters are used to emphasize floral notes (especially rose).