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63670

Sigma-Aldrich

(±)-Menthol

racemic, ≥98.0% (GC)

Synonym(s):
2-Isopropyl-5-methylcyclohexanol, Racemic menthol, Hexahydrothymol, Menthol
Empirical Formula (Hill Notation):
C10H20O
CAS Number:
Molecular Weight:
156.27
Beilstein:
3194263
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

vapor pressure

0.8 mmHg ( 20 °C)

assay

≥98.0% (GC)

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

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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.

Packaging

100, 500 g in poly bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

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

Certificate of Analysis

Certificate of Origin

"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)
"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)
Zongde Wang et al.
Bioorganic & medicinal chemistry letters, 18(9), 2854-2859 (2008-04-22)
A new class of low-toxicity mosquito repellents is synthesized from alpha- and beta-pinene in terpenoid compounds and preliminary biological tests show promising mosquito repellency. Statistical modeling is built using Codessa in order to reveal the quantitative relationship between the structure...
María Ll Valero et al.
PloS one, 7(12), e51825-e51825 (2012-12-20)
Overexpression of the cation-permeable channel TRPM8 in prostate cancers might represent a novel opportunity for their treatment. Inhibitors of TRPM8 reduce the growth of prostate cancer cells. We have used two recently described and highly specific blockers, AMTB and JNJ41876666...
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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