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:
Molecular Weight:
156.27
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
201-939-0
Beilstein/REAXYS Number:
3194263
MDL number:
Assay:
≥98.0% (GC)
Form:
solid
vapor pressure
0.8 mmHg ( 20 °C)
Quality Level
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)
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.
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signalword
Warning
hcodes
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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"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)
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