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Merck
CN

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

Key Documents

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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.)

functional group

hydroxyl

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
BCCM7954
STBL0522
BCCC7250
BCBW4149
BCBT6056

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"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)
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
Miranda R Jones et al.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology, 22(2), 224-232 (2012-12-20)
In the United States, cigarette flavorings are banned, with the exception of menthol. The cooling effects of menthol could facilitate the absorption of tobacco toxicants. We examined levels of biomarkers of tobacco exposure among U.S. smokers of menthol and nonmenthol
Andrew A Strasser et al.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology, 22(3), 382-389 (2013-01-22)
As part of the Family Smoking Prevention and Tobacco Control Act, the U.S. Food and Drug Administration charged the Tobacco Products Scientific Advisory Committee with developing a report and recommendations about the effect of menthol in cigarettes on the public
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