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W266590

Sigma-Aldrich

L-Menthol

≥99%, FCC, FG

Synonym(s):

(1R,2S,5R)-(−)-Menthol, (−)-Menthol, (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol, 5-Methyl-2-(1-methylethyl)cyclohexanol

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About This Item

Empirical Formula (Hill Notation):
C10H20O
CAS Number:
2216-51-5
Molecular Weight:
156.27
FEMA Number:
2665
Beilstein:
1902293
EC Number:
218-690-9
Council of Europe no.:
65c
MDL number:
MFCD00062979
UNSPSC Code:
12164502
PubChem Substance ID:
24901229
Flavis number:
02.015
NACRES:
NA.21

biological source

synthetic

Quality Level

400

grade

FG
Kosher

reg. compliance

EU Regulation 1334/2008 & 178/2002
FCC
FDA 21 CFR 117
FDA 21 CFR 172.515

vapor pressure

0.8 mmHg ( 20 °C)

Assay

≥99%

optical activity

[α]22/D −49°, c = 10 in 95% ethanol

bp

212 °C (lit.)

mp

41-45 °C (lit.)

density

0.89 g/mL at 25 °C (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

Organoleptic

cooling; minty; camphoraceous

SMILES string

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

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

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General description

Natural occurrence: Mentha species.
L-Menthol is the principal component of peppermint oil. It is widely used in confectionaries cosmetics and toothpaste for its characteristic peppermint flavor and cooling effect.

Application


  • Chemical Characterization of Terpene-Based Hydrophobic Eutectic Solvents and Their Application for Pb(II) Complexation during Solvent Extraction Procedure.: Explores the use of l-menthol-based hydrophobic eutectic solvents for efficient heavy metal extraction, highlighting its potential in environmental clean-up and recovery of valuable metals from waste streams (Suljkanović et al., 2024).

  • Eco-Friendly Production of Boron Nitride Nanosheets via Deep Eutectic Solvents and Their Application in Enhancing Thermal Conductivity of PVDF Composites.: Investigates l-menthol′s role in synthesizing boron nitride nanosheets using green chemistry approaches, enhancing the material properties of composites used in electronics and engineering applications (Sang et al., 2024).

  • Supramolecular Structure of the β-Cyclodextrin Metal-Organic Framework Optimizes Iodine Stability and Its Co-delivery with l-Menthol for Antibacterial Applications.: Demonstrates the novel use of l-menthol in conjunction with metal-organic frameworks for developing advanced antibacterial delivery systems, offering enhanced stability and efficacy in medical and health care products (Zhao et al., 2024).

  • Acid-based deep eutectic solvents followed by GFAAS for the speciation of As(III), As(V), total inorganic arsenic and total arsenic in rice samples.: Utilizes l-menthol in innovative solvent systems for arsenic speciation, contributing to safer food production and effective monitoring of contaminants in agricultural products (Fattahi et al., 2024).

Biochem/physiol Actions

Taste at 25 ppm

Other Notes

The substance W266590 has no REACH registration because the only supported use is the use in medicinal products for human or veterinary use or in food or feedingstuffs according to article 2 of the REACH Regulation (EC) No 1907/2006.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Optimized synthesis of lipase-catalyzed l-menthyl butyrate by Candia rugosa lipase.
Shih L, et al.
Food Chemistry, 100(3), 1223-1228 (2007)
Thomas Voets et al.
Nature chemical biology, 3(3), 174-182 (2007-02-13)
TRPM8, a member of the transient receptor potential (TRP) channel superfamily, is expressed in thermosensitive neurons, in which it functions as a cold and menthol sensor. TRPM8 and most other temperature-sensitive TRP channels (thermoTRPs) are voltage gated; temperature and ligands
H G Grigoleit et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 12(8), 612-616 (2005-08-27)
The principal pharmacodynamic effect of peppermint oil relevant to the gastrointestinal tract is a dose-related antispasmodic effect on the smooth musculature due to the interference of menthol with the movement of calcium across the cell membrane. The choleretic and antifoaming
Robert J Stein et al.
The Journal of urology, 172(3), 1175-1178 (2004-08-18)
Overactive bladder symptoms due to various etiologies have been successfully treated with capsaicin by desensitization of the temperature sensitive vanilloid receptor TRPV1. Recently another temperature sensitive receptor, TRPM8, activated by menthol and cool temperatures (8C to 28C) was described that
H F Stich et al.
Cancer letters, 15(3), 193-202 (1982-03-01)
Saliva of volunteers chewing betel quid, cured betel nut (Areca catechu), betel leaves (Piper betle), a mixture of quid ingredients (dried betel nut flakes, catechu, cardamon, lime, copra and menthol) and Indian tobacco was collected and examined for its genotoxic
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