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Merck
CN

63660

(−)-Menthol

analytical standard

Synonym(s):

(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol, 5-Methyl-2-(1-methylethyl)cyclohexanol

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About This Item

Empirical Formula (Hill Notation):
C10H20O
CAS Number:
2216-51-5
Molecular Weight:
156.27
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
329759885
EC Number:
218-690-9
Beilstein/REAXYS Number:
1902293
MDL number:
MFCD00062979

Key Documents

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Product Name

(−)-Menthol, analytical standard

InChI key

NOOLISFMXDJSKH-KXUCPTDWSA-N

InChI

1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10-/m1/s1

SMILES string

CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O

grade

analytical standard

assay

≥99.0% (sum of enantiomers, GC)

optical activity

[α]20/D −50±1°, c = 10% in ethanol

optical purity

enantiomeric ratio: ≥99:1 (GC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

~43 °C

application(s)

food and beverages

format

neat

Quality Level

100

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

General description

(-)-Menthol is a cyclic terpene alcohol that occurs in mentha species.It is responsible for their distinctive odor and flavor.

Other Notes

Important resolving agent for acids, recent applications include; Crystallization-induced asymmetric transformation of malonates ; Chiral auxiliary
This compound is commonly found in plants of the genus: mentha

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

201.2 °F - closed cup

flash_point_c

94 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL6191
BCCM5064
BCCH1139
BCCC3032
BCBW5590

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Menthol: a refreshing look at this ancient compound
Patel T, et al.
Journal of the American Academy of Dermatology, 57(5), 873-878 (2007)
N. Katagiri et al.
The Journal of Organic Chemistry, 53, 227-227 (1988)
Ariane Leite Rozza et al.
PloS one, 9(1), e86686-e86686 (2014-01-28)
The aim of this research was to investigate the anti-apoptotic, antioxidant and anti-inflammatory properties of menthol against ethanol-induced gastric ulcers in rats. Wistar rats were orally treated with vehicle, carbenoxolone (100 mg/kg) or menthol (50 mg/kg) and then treated with
M. Ihara et al.
Journal of the Chemical Society. Chemical Communications, 9-9 (1988)
J.-M. Brunel et al.
The Journal of Organic Chemistry, 58, 7313-7313 (1993)
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