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15785

Sigma-Aldrich

(−)-Menthol

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

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
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

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

201.2 °F - closed cup

Flash Point(C)

94 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

15785-4X1KG:
15785-100G:
15785-6X100G:
15785-BULK:
15785-6X1KG:
15785-1KG:
15785-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
STBL3250
STBK7322
STBK4984
STBJ6318
STBH5981

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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)
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)
An asymmetric approach to coumarin anticoagulants via hetero-Diels-Alder cycloaddition.
Cravotto G, et al.
Tetrahedron Asymmetry, 12(5), 707-709 (2001)
Novel 2-(hydroxyalkyl) pyridines derived from the chiral pool.
Adolfsson H, et al.
Tetrahedron Asymmetry, 7(7), 1967-1972 (1996)
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