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224464

Sigma-Aldrich

(1S,2R,5S)-(+)-Menthol

99%

Synonym(s):

(+)-Menthol, (1S,2R,5S)-2-Isopropyl-5-methylcyclohexanol

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About This Item

Empirical Formula (Hill Notation):
C10H20O
CAS Number:
15356-60-2
Molecular Weight:
156.27
Beilstein/REAXYS Number:
1902292
EC Number:
239-387-8
MDL number:
MFCD00062983
UNSPSC Code:
12352212
PubChem Substance ID:
24853440
NACRES:
NA.22

vapor pressure

0.8 mmHg ( 20 °C)

Quality Level

100

assay

99%

form

solid

optical activity

[α]23/D +48°, c = 10 in ethanol

optical purity

ee: 96% (GLC)

bp

103-104 °C/9 mmHg (lit.)

mp

43-44 °C (lit.)

SMILES string

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

InChI

1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10-/m0/s1

InChI key

NOOLISFMXDJSKH-AEJSXWLSSA-N

Gene Information

human ... UGT1A4(54657)

General description

(1S,2R,5S)-(+)-menthol is a chiral secondary alcohol. Its alcohol group can be protected as 2-tetrahydrofuranyl ether by reacting with bromotrichloromethane and tetrahydrofuran.

Application

(1S,2R,5S)-(+)-menthol can undergo acylation with acid anhydrides in the presence of trimethylsilyl trifluoromethanesulfonate to form the corresponding acylated products.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

213.8 °F - closed cup

flash_point_c

101 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBD8259V
1451624
S18069V
STBB6236V
STBB6236

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Sigma-Aldrich

218367

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DL-Menthol ≥95%, FCC, FG

Sigma-Aldrich

W266507

DL-Menthol

An efficient and extremely mild method for protecting alcohols as 2-tetrahydrofuranyl ethers.
Barks JM, et al.
Tetrahedron Letters, 41(32), 6249-6252 (2000)
An extremely powerful acylation reaction of alcohols with acid anhydrides catalyzed by trimethylsilyl trifluoromethanesulfonate.
Procopiou PA, et al.
The Journal of Organic Chemistry, 63(7), 2342-2347 (1998)
Shannon Kozlovich et al.
Drug metabolism and disposition: the biological fate of chemicals, 47(12), 1388-1396 (2019-10-04)
Menthol, which creates mint flavor and scent, is often added to tobacco in both menthol and nonmenthol cigarettes. A potent tobacco carcinogen, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), is extensively metabolized to its equally carcinogenic metabolite 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) as (R)- or (S)-NNAL enantiomers. NNAL

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