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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)

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Andrea C Villanti et al.
American journal of preventive medicine, 44(4), 388-391 (2013-03-19)
Passage of the U.S. Family Smoking Prevention and Tobacco Control Act in 2009 led to a ban on the sale of flavored cigarettes, largely because of studies showing targeting of these products to youth and young adults. There are no
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
Yang Chen et al.
International journal of pharmaceutics, 443(1-2), 120-127 (2013-01-22)
To explore the structure-activity relationship for terpenes as transdermal penetration enhancers, unsaturated menthol analogues were synthesized in our study, including p-menth-1-en-3-ol (Compd 1), p-menth-4-en-3-ol (Compd 2), p-menth-4(8)-en-3-ol (Compd 3) and p-menth-8-en-3-ol (Compd 4). Their enhancing activity on the penetration of
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