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CHEBI:15409 - (−)-menthol

ChEBI IDCHEBI:15409
ChEBI Name(−)-menthol
Stars
ASCII Name(-)-menthol
DefinitionA p-menthan-3-ol which has (1R,2S,5R)-stereochemistry. It is the most common naturally occurring enantiomer.
Secondary ChEBI IDsCHEBI:101, CHEBI:10779, CHEBI:18493
Last Modified16 May 2023
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC10H20O
Net Charge0
Average Mass156.269
Monoisotopic Mass156.15142
SMILESCC(C)[C@@H]1CC[C@@H](C)C[C@H]1O
InChIInChI=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
InChIKeyNOOLISFMXDJSKH-KXUCPTDWSA-N
Wikipedia
Roles Classification
Biological Role:
volatile oil component  Any plant metabolite that is found naturally as a component of a volatile oil.
Applications:
antipruritic drug  A drug, usually applied topically, that relieves pruritus (itching).
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.
ChEBI Ontology
Outgoing Relation(s)
(−)-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 Relation(s)
(−)-menthyl β-D-glucoside (CHEBI:15411) has functional parent (−)-menthol (CHEBI:15409)
4-formyl-2-methoxyphenyl L-menthyl glutarate (CHEBI:195230) 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  Source
levomentholChemIDplus
levomentholumWHO MedNet
lévomentholWHO MedNet
levomentolWHO MedNet
Synonyms  Source
(-)-MentholKEGG COMPOUND
(1alpha,2beta,5alpha)-5-methyl-2(1-methylethyl)cyclohexanolChEBI
L-MentholKEGG COMPOUND
(1R-(1-α,2-β,5-α))-5-methyl-2-(1-methylethyl)cyclohexanolChemIDplus
(−)-(1R,3R,4S)-mentholChemIDplus
(1R,3R,4S)-(−)-mentholNIST Chemistry WebBook
UniProt Name  Source
(−)-mentholUniProt
Manual XrefsDatabases
C00400KEGG COMPOUND
LMPR0102090001LIPID MAPS
DB00825DrugBank
D00064KEGG DRUG
MentholWikipedia
CN101602651Patent
US2011313205Patent
HMDB0003352HMDB
--MENTHOLMetaCyc
C00000810KNApSAcK
934DrugCentral
Registry NumbersSources
Reaxys:1902293Reaxys
CAS:2216-51-5KEGG COMPOUND
CAS:2216-51-5NIST Chemistry WebBook
Citations