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15785

Sigma-Aldrich

(−)-Menthol

puriss., meets analytical specification of Ph. Eur., BP, USP, 98.0-102.0%

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Synonym(s):
(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol, 5-Methyl-2-(1-methylethyl)cyclohexanol
Empirical Formula (Hill Notation):
C10H20O
CAS Number:
2216-51-5
Molecular Weight:
156.27
Beilstein:
1902293
EC Number:
218-690-9
MDL number:
MFCD00062979
UNSPSC Code:
12352001
PubChem Substance ID:
57647522
NACRES:
NA.22

grade

puriss.

Quality Level

200

Assay

98.0-102.0%

form

solid

optical activity

[α]20/D −48 to −51°, c = 10% in ethanol

quality

meets analytical specification of Ph. Eur., BP, USP

impurities

acidity or alcalinity, complies
 related subst., complies
≤0.05% non-volatile matter

mp

41-44 °C

suitability

in accordance for appearance of solution

application(s)

pharmaceutical (small molecule)

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-/m1/s1

InChI key

NOOLISFMXDJSKH-KXUCPTDWSA-N

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General description

(-)-Menthol is a monoterpene.

Application

(-)-Menthol may be used to synthesize:
  • chiral enantiopure 2-(1-hydroxyalkyl)pyridines, which can react with phosphorus oxychloride to form C3-symmetric tripodal ligands
  • menthylphosphorodichioridite, a chiral derivatizing agent for the determination of enantiomeric purity of chiral diols or diamines by 31P NMR spectroscopy
  • (2R,4S)-2,3,4,5-tetrahydro-2-(-)-menthyloxy-2-methyl-4-phenylpyrano-[3,2-c]-benzopyran-5-one, an intermediate to prepare a warfarin analog
It may also be used as a chiral auxiliary, to induce chirality while synthesizing (-)-horsfiline.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

WGK

WGK 1

Flash Point(F)

201.2 °F

Flash Point(C)

94 °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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A new 31P NMR method for the enantiomeric excess determination of diols and secondary diamines with C 2 symmetry.
Tetrahedron Asymmetry, 6(9), 2353-2356 (1995)
Novel 2-(hydroxyalkyl) pyridines derived from the chiral pool.
Adolfsson H, et al.
Tetrahedron Asymmetry, 7(7), 1967-1972 (1996)
An asymmetric approach to coumarin anticoagulants via hetero-Diels-Alder cycloaddition.
Cravotto G, et al.
Tetrahedron Asymmetry, 12(5), 707-709 (2001)
Marei GI, et al.
Pesticide Biochemistry and Physiology, 103(1), 56-61 (2012)
Oxindole alkaloids. A novel non-biomimetic entry to (-)-Horsfiline.
Palmisano G, et al.
Tetrahedron Asymmetry, 7(1), 1-4 (1996)
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