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Merck

W266523

L-Menthol

greener alternative

natural, ≥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
Council of Europe no.:
65c
UNSPSC Code:
12164502
PubChem Substance ID:
24901227
Flavis number:
2.218
EC Number:
218-690-9
NACRES:
NA.21
MDL number:
MFCD00062979
Beilstein/REAXYS Number:
1902293
Organoleptic:
minty; cooling; peppermint
Grade:
FG, Halal, Kosher, natural
Food allergen:
no known allergens

Key Documents

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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

grade

FG, Halal, Kosher, natural

reg. compliance

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

vapor pressure

0.8 mmHg ( 20 °C)

assay

≥99%

optical activity

[α]20/D −49°, c = 10 in 95% ethanol

greener alternative product characteristics

Less Hazardous Chemical Syntheses
Use of Renewable Feedstocks
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

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

fragrance allergen

no known allergens

greener alternative category

Aligned

organoleptic

minty; cooling; peppermint

Quality Level

300, 400

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General description

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

L-Menthol can be used as a model flavor compound to prepare flavor encapsulated porous cellulose particles for food processing applications.

Biochem/physiol Actions

Taste at 25 ppm

Other Notes

Natural occurrence: Mentha species.

Disclaimer

The substance W266523 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

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

201.2 °F - closed cup

flash_point_c

94 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR4802
SHBR1676
SHBQ5271
SHBR0412
SHBQ5270

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An investigation of flavor encapsulation comprising of regenerated cellulose as core and carboxymethyl cellulose as wall
Ma M, et al.
Iranian Polymer Journal, 22(9), 689-695 (2013)
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
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
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
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