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Details

Stereochemistry RACEMIC
Molecular Formula C10H20O
Molecular Weight 156.2656
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RACEMENTHOL

SMILES

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

InChI

InChIKey=NOOLISFMXDJSKH-KXUCPTDWSA-N
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

HIDE SMILES / InChI

Molecular Formula C10H20O
Molecular Weight 156.2656
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: description was created based on several sources, including: http://www.tera.org/OARS/Menthol%20WEEL%20FINAL.pdf | http://www.inchem.org/documents/sids/sids/MENTHOLS.pdf

Levomenthol is a stereoisomer of menthol, which is most frequently encountered in natural products, such as peppermint oil. Menthol is used in OTC products for relief of minor sore throat, as a topical analgesic to releive minor aches, as an antipruritic to reduce itching, as a decongestant, as an antispasmodic and a smooth muscle relaxant in upper gastrointestinal endoscopy and other conditions.

CNS Activity

Curator's Comment:: Known to disrupt tight junctions in blood brain barrier

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
37.8 µM [IC50]
300.0 µM [IC50]
Target ID: Q7Z2W7
Gene ID: 79054.0
Gene Symbol: TRPM8
Target Organism: Homo sapiens (Human)
30.0 µM [EC50]
Target ID: O75762
Gene ID: 8989.0
Gene Symbol: TRPA1
Target Organism: Homo sapiens (Human)
68.0 µM [IC50]
Target ID: P41145
Gene ID: 4986.0
Gene Symbol: OPRK1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
BENGAY

Approved Use

temporarily relieves the minor aches and pains of muscles and joints associated with a simple backache, arthritis, strains, bruises, sprains.
Palliative
BENGAY

Approved Use

temporarily relieves the minor aches and pains of muscles and joints associated with a simple backache, arthritis, strains, bruises, sprains.
Palliative
Unknown

Approved Use

Unknown
Palliative
VICKS VAPORUB

Approved Use

On chest and throat, temporarily relieves cough due to common cold
Primary
VICKS VAPORUB

Approved Use

On muscles and joints, temporarily relieves minor aches and pains
Primary
CVS ANTI ITCH

Approved Use

For the temporary relief of pain and itching associated with minor skin irritations such as poison ivy/oak/sumac, sunburn, insect bites and minor cuts and scrapes.
Palliative
VICKS VAPORUB

Approved Use

Treatment for rhinitis that is associated with acute upper respiratory tract infection and allergy
Palliative
Unknown

Approved Use

Unknown
Primary
FRESCOLAT ML

Approved Use

The compund is uses as a flavoring ingredient and in cosmetics as a cooling agent
PubMed

PubMed

TitleDatePubMed
The effects of D and L isomers of menthol upon nasal sensation of airflow.
1988 Jun
Menthone and isomenthone biosynthesis in Pelargonium tomentosum Jacq.
2001
Final report on the safety assessment of Mentha Piperita (Peppermint) Oil, Mentha Piperita (Peppermint) Leaf Extract, Mentha Piperita (Peppermint) Leaf, and Mentha Piperita (Peppermint) Leaf Water.
2001
Understanding childhood asthma in focus groups: perspectives from mothers of different ethnic backgrounds.
2001
The nicotine inhaler: clinical pharmacokinetics and comparison with other nicotine treatments.
2001
Metabolism of (R)-(+)-pulegone in F344 rats.
2001 Dec
Fullerene modified supported lipid membrane as sensitive element of sensor for odorants.
2001 Dec
Pulmonary peptide delivery: effect of taste-masking excipients on leuprolide suspension metered-dose inhalers.
2001 Nov
Systematic studies on structure and physiological activity of cyclic alpha-keto enamines, a novel class of "cooling" compounds.
2001 Nov
Smoking and pregnancy outcome among African-American and white women in central North Carolina.
2001 Nov
Effect of Mentha x piperita essential oil and monoterpenes on cucumber root membrane potential.
2001 Nov
The development of new methods for the recycling of chiral catalysts.
2001 Nov
Physiology. Cold current in thermoreceptive neurons.
2001 Oct 4
Effect of melting point of chiral terpenes on human stratum corneum uptake.
2001 Oct 9
Molecular-imprinted, polymer-coated quartz crystal microbalances for the detection of terpenes.
2001 Sep 1
Feasibility study of repeated harvesting of menthol from biologically viable Mentha x piperata using ultrasonic extraction.
2001 Sep-Oct
Smoking among Asian American and Hawaiian/Pacific Islander youth: data from the 2000 National Youth Tobacco Survey.
2001 Winter-Spring
Penetration enhancing effect of menthol on the percutaneous flux of nicardipine hydrochloride through excised rat epidermis from hydroxypropyl cellulose gels.
2002
An analysis of the mainstream smoke chemistry of samples of the U.S. cigarette market acquired between 1995 and 2000.
2002 Apr
A chlorinated monoterpene ketone, acylated beta-sitosterol glycosides and a flavanone glycoside from Mentha longifolia (Lamiaceae).
2002 Apr
Menthol: a natural analgesic compound.
2002 Apr 12
Extraction of thymol, eucalyptol, menthol, and camphor residues from honey and beeswax. Determination by gas chromatography with flame ionization detection.
2002 Apr 19
Voltage-dependent block of neuronal and skeletal muscle sodium channels by thymol and menthol.
2002 Aug
Cold- and menthol-sensitive C afferents of cat urinary bladder.
2002 Aug 15
Transdermal drug delivery of imipramine hydrochloride. I. Effect of terpenes.
2002 Feb 19
In vitro skin permeation of morphine hydrochloride during the finite application of penetration-enhancing system containing water, ethanol and l-menthol.
2002 Jan
Effect of the vesicular-arbuscular mycorrhizal (VAM) fungus Glomus fasciculatum on the essential oil yield related characters and nutrient acquisition in the crops of different cultivars of menthol mint (Mentha arvensis) under field conditions.
2002 Jan
Factors affecting the resolution of dl-menthol by immobilized lipase-catalyzed esterification in organic solvent.
2002 Jan 16
Phytochemical induction by herbivores could affect quality of essential oils from aromatic plants.
2002 Jul 3
Antimicrobial screening of Mentha piperita essential oils.
2002 Jul 3
Field evaluation of three plant-based insect repellents against malaria vectors in Vaca Diez Province, the Bolivian Amazon.
2002 Jun
Mentholated cigarettes and smoking cessation: findings from COMMIT. Community Intervention Trial for Smoking Cessation.
2002 Jun
Preparation and self-assembly of chiral porphyrin diads on the gold electrodes of quartz crystal microbalances: a novel potential approach to the development of enantioselective chemical sensors.
2002 Jun 3
The dark side of marketing seemingly "Light" cigarettes: successful images and failed fact.
2002 Mar
Specificity of cold thermotransduction is determined by differential ionic channel expression.
2002 Mar
Essential oil composition of sachalinmint from Norway detected by solid-phase microextraction and gas chromatography-mass spectrometry analysis.
2002 Mar 13
Signal transduction. Hot and cold TRP ion channels.
2002 Mar 22
Identification of a cold receptor reveals a general role for TRP channels in thermosensation.
2002 Mar 7
Anti-HIV activity of thiosemicarbazone and semicarbazone derivatives of (+/-)-3-menthone.
2002 May
Insecticidal properties of essential plant oils against the mosquito Culex pipiens molestus (Diptera: Culicidae).
2002 May
Analysis of menthol in three traditional Chinese medicinal herbs and their compound formulation by GC-MS.
2002 May
[TRP channels--sensitive for heat and cold, capsaicin and menthol].
2002 May 16
Ion channels activated by cold and menthol in cultured rat dorsal root ganglion neurones.
2002 May 17
A novel treatment of postherpetic neuralgia using peppermint oil.
2002 May-Jun
Evaluation of peppermint oil and ascorbyl palmitate as inhibitors of cytochrome P4503A4 activity in vitro and in vivo.
2002 Sep
Characterization of essential oils from lamiaceae species by fourier transform Raman spectroscopy.
2002 Sep 25
Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging plate reader (FLIPR) assay.
2004 Feb
Fragrance material review on d-menthol.
2008 Nov
Different effects of l- and d-menthol on the microstructure of ceramide 5/cholesterol/palmitic acid bilayers.
2010 Dec 15
Effects of d-menthol stress on the growth of and microcystin release by the freshwater cyanobacterium Microcystis aeruginosa FACHB-905.
2014 Oct
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: maximum daily exposure on the skin of 0.0573 mg/kg/day https://www.ncbi.nlm.nih.gov/pubmed/18640220
The compound is recommended for use as a flavor in concentrations of 0.005% to 0.2% and in cosmetic and other external products in concentrations ranging from 0.2% to 2.0%. The maximum recommended amount of menthyl lactate as per the product literature is therefore 2.0% by weight, which would correspond 1.3% by weight of the menthol moiety.
Route of Administration: Topical
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:36:20 UTC 2021
Edited
by admin
on Fri Jun 25 20:36:20 UTC 2021
Record UNII
YS08XHA860
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RACEMENTHOL
HSDB   INN   WHO-DD  
INN  
Official Name English
DL-MENTHOL
Common Name English
MENTHOL, (+/-)-
Systematic Name English
RACEMENTHOL [WHO-DD]
Common Name English
MENTHOL, DL-
Common Name English
FEMA NO. 2665, (+/-)-
Code English
RAC-MENTHOL
Common Name English
(1R,2S,5R)-REL-5-METHYL-2-(1-METHYLETHYL)CYCLOHEXANOL
Common Name English
RACEMENTHOL [INN]
Common Name English
NSC-2603
Code English
MENTHOL, CIS-1,3,TRANS-1,4-
Common Name English
(+/-)-MENTHOL
Systematic Name English
(+/-)-(1R*,3R*,4S*)-MENTHOL
Systematic Name English
CYCLOHEXANOL, 5-METHYL-2-(1-METHYLETHYL)-, (1.ALPHA.,2.BETA.,5.ALPHA.)-
Common Name English
MEGGEZONE
Common Name English
MENTHOL RACEMATE [MI]
Common Name English
CYCLOHEXANOL, 5-METHYL-2-(1-METHYLETHYL)-, (1R,2S,5R)-REL-
Common Name English
RACEMENTHOL [HSDB]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C245
Created by admin on Fri Jun 25 20:36:20 UTC 2021 , Edited by admin on Fri Jun 25 20:36:20 UTC 2021
NCI_THESAURUS C860
Created by admin on Fri Jun 25 20:36:20 UTC 2021 , Edited by admin on Fri Jun 25 20:36:20 UTC 2021
Code System Code Type Description
RXCUI
1430390
Created by admin on Fri Jun 25 20:36:20 UTC 2021 , Edited by admin on Fri Jun 25 20:36:20 UTC 2021
PRIMARY RxNorm
HSDB
89-78-1
Created by admin on Fri Jun 25 20:36:20 UTC 2021 , Edited by admin on Fri Jun 25 20:36:20 UTC 2021
PRIMARY
EPA CompTox
89-78-1
Created by admin on Fri Jun 25 20:36:20 UTC 2021 , Edited by admin on Fri Jun 25 20:36:20 UTC 2021
PRIMARY
DRUG BANK
DB14123
Created by admin on Fri Jun 25 20:36:20 UTC 2021 , Edited by admin on Fri Jun 25 20:36:20 UTC 2021
PRIMARY
NCI_THESAURUS
C75073
Created by admin on Fri Jun 25 20:36:20 UTC 2021 , Edited by admin on Fri Jun 25 20:36:20 UTC 2021
PRIMARY
FDA UNII
YS08XHA860
Created by admin on Fri Jun 25 20:36:20 UTC 2021 , Edited by admin on Fri Jun 25 20:36:20 UTC 2021
PRIMARY
INN
6724
Created by admin on Fri Jun 25 20:36:20 UTC 2021 , Edited by admin on Fri Jun 25 20:36:20 UTC 2021
PRIMARY
ChEMBL
CHEMBL256087
Created by admin on Fri Jun 25 20:36:20 UTC 2021 , Edited by admin on Fri Jun 25 20:36:20 UTC 2021
PRIMARY
CAS
89-78-1
Created by admin on Fri Jun 25 20:36:20 UTC 2021 , Edited by admin on Fri Jun 25 20:36:20 UTC 2021
PRIMARY
ChEMBL
CHEMBL2106989
Created by admin on Fri Jun 25 20:36:20 UTC 2021 , Edited by admin on Fri Jun 25 20:36:20 UTC 2021
PRIMARY
ECHA (EC/EINECS)
201-939-0
Created by admin on Fri Jun 25 20:36:20 UTC 2021 , Edited by admin on Fri Jun 25 20:36:20 UTC 2021
PRIMARY
MERCK INDEX
M7175
Created by admin on Fri Jun 25 20:36:20 UTC 2021 , Edited by admin on Fri Jun 25 20:36:20 UTC 2021
PRIMARY
EVMPD
SUB10232MIG
Created by admin on Fri Jun 25 20:36:20 UTC 2021 , Edited by admin on Fri Jun 25 20:36:20 UTC 2021
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
PARENT -> CONSTITUENT ALWAYS PRESENT
Compound measured as 3.50% of the composition of the steam distillate of Elymus repens rhizome as per R Boesel in Planta Medica iss:4 pg:399-400, 1989.
Related Record Type Details
ACTIVE MOIETY