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63670

Sigma-Aldrich

(±)-Menthol

racemic, ≥98.0% (GC)

Synonym(s):

Menthol, Racemic menthol, 2-Isopropyl-5-methylcyclohexanol, Hexahydrothymol

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About This Item

Empirical Formula (Hill Notation):
C10H20O
CAS Number:
89-78-1
Molecular Weight:
156.27
Beilstein:
3194263
EC Number:
201-939-0
MDL number:
MFCD00001484
UNSPSC Code:
12352100
PubChem Substance ID:
57651951
NACRES:
NA.22

vapor pressure

0.8 mmHg ( 20 °C)

Quality Level

100

Assay

≥98.0% (GC)

form

solid

quality

racemic

bp

216 °C (lit.)

mp

34-36 °C (lit.)

density

0.89 g/mL at 25 °C (lit.)

SMILES string

CC(C)C1CCC(C)CC1O

InChI

1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3

InChI key

NOOLISFMXDJSKH-UHFFFAOYSA-N

Gene Information

human ... TRPA1(8989) , TRPM8(79054)

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General description

(±)-Menthol (racemic menthol) can be synthesized via hydrogenation of citral.

Application

(±)-Menthol (racemic menthol) can be transformed to (-)-menthyl acetate by using Candida rugosa lipase(CRL) and lipase PS(from Pseudomonas cepacia) as catalysts.

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)

204.8 °F

Flash Point(C)

96 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG6828
BCCC7250
BCBW4149
BCBT6056
BCBQ3275V

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"Lipase-catalyzed resolution of p-menthan-3-ols monoterpenes: preparation of the enantiomer-enriched forms of menthol, isopulegol, trans-and cis-piperitol, and cis-isopiperitenol"
Serra S, et al.
Tetrahedron Asymmetry, 14(21), 3313-3319 (2003)
"Design, scale up and safe piloting of thymol hydrogenation and menthol racemisation"
Dudas J and Hanika J
Chemical Engineering Research and Design, 87(01), 83-90 (2009)
Joanne D'Silva et al.
American journal of preventive medicine, 43(5 Suppl 3), S242-S248 (2012-10-25)
Menthol cigarettes account for 25% of the market in the U.S. The Food and Drug Administration currently is considering regulatory action on tobacco products, including a ban on menthol cigarettes. With 39% of menthol smokers reporting that they would quit
Shengyi Lu et al.
European journal of oral sciences, 121(1), 29-35 (2013-01-22)
This study was designed to investigate the effect of surrogate orofacial pain models on the quantitative sensory testing (QST) profile in healthy participants. Capsaicin, menthol, or saline (control) were applied topically onto the gingiva of 15 healthy subjects for 15 min.
Abrar Ashoor et al.
The Journal of pharmacology and experimental therapeutics, 347(2), 398-409 (2013-08-24)
The effects of alcohol monoterpene menthol, a major active ingredient of the peppermint plant, were tested on the function of human 5-hydroxytryptamine type 3 (5-HT3) receptors expressed in Xenopus laevis oocytes. 5-HT (1 μM)-evoked currents recorded by two-electrode voltage-clamp technique
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