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Merck

63670

(±)-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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
57651951
EC Number:
201-939-0
Beilstein/REAXYS Number:
3194263
MDL number:
MFCD00001484
Assay:
≥98.0% (GC)
Form:
solid

Key Documents

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InChI key

NOOLISFMXDJSKH-UHFFFAOYSA-N

InChI

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

SMILES string

CC(C)C1CCC(C)CC1O

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.)

functional group

hydroxyl

Quality Level

100

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

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

204.8 °F

flash_point_c

96 °C

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCP2212
BCCM7954
STBL0522
BCCC7250
BCBW4149

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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)
Brandon J Henderson et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 36(10), 2957-2974 (2016-03-11)
Upregulation of β2 subunit-containing (β2*) nicotinic acetylcholine receptors (nAChRs) is implicated in several aspects of nicotine addiction, and menthol cigarette smokers tend to upregulate β2* nAChRs more than nonmenthol cigarette smokers. We investigated the effect of long-term menthol alone on
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
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
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