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W266523

Sigma-Aldrich

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
Beilstein:
1902293
EC Number:
218-690-9
Council of Europe no.:
65c
MDL number:
MFCD00062979
UNSPSC Code:
12164502
PubChem Substance ID:
24901227
Flavis number:
2.218
NACRES:
NA.21

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

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

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

Signal Word

Warning

Hazard Statements

H315,H319

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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Certificates of Analysis (COA)

Lot/Batch Number
SHBM9898
SHBM3769
MKCH7110
MKCF6497
MKCD8501

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SAFC

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USP

1381709

Menthol

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BP772

Levomenthol

L-Menthone mixture of isomers, ≥96%, FCC, FG

Sigma-Aldrich

W266701

L-Menthone

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
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
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