W266590
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:
Molecular Weight:
156.27
FEMA Number:
2665
Beilstein:
1902293
EC Number:
Council of Europe no.:
65c
MDL number:
UNSPSC Code:
12164502
PubChem Substance ID:
Flavis number:
02.015
NACRES:
NA.21
Recommended Products
biological source
synthetic
Quality Level
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2
Storage Class Code
11 - Combustible Solids
WGK
WGK 1
Flash Point(F)
201.2 °F - closed cup
Flash Point(C)
94 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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
Anne-Mette Haahr et al.
Physiology & behavior, 82(2-3), 531-540 (2004-07-28)
During chewing, the oral cavity functions like a bellow, forcing volatile flavour compounds into the exhaling air to the nasal compartment. Accordingly, we hypothesised that flavour release from chewing gum is predominantly governed by chewing frequency (CF), although other oral
Tibor Rohács et al.
Nature neuroscience, 8(5), 626-634 (2005-04-27)
The subjective feeling of cold is mediated by the activation of TRPM8 channels in thermoreceptive neurons by cold or by cooling agents such as menthol. Here, we demonstrate a central role for phosphatidylinositol 4,5-bisphosphate (PI(4,5)P(2)) in the activation of recombinant
A Gelal et al.
Clinical pharmacology and therapeutics, 66(2), 128-135 (1999-08-25)
Menthol is widely used in a variety of commercial products and foods, but its clinical pharmacology is not well studied. To determine the disposition kinetics and to examine subjective and cardiovascular effects of menthol, we conducted a crossover placebo-controlled study
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