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Merck
CN

M2780

(1R,2S,5R)-(−)-Menthol

ReagentPlus®, 99%

Synonym(s):

(−)-Menthol, (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:
12352001
NACRES:
NA.22
PubChem Substance ID:
24896767
EC Number:
218-690-9
Beilstein/REAXYS Number:
1902293
MDL number:
MFCD00062979

Key Documents

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Product Name

(1R,2S,5R)-(−)-Menthol, ReagentPlus®, 99%

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

biological source

synthetic (organic)

vapor pressure

0.8 mmHg ( 20 °C)

product line

ReagentPlus®

assay

99%

optical activity

[α]20/D −50°, c = 10 in 95% ethanol

optical purity

ee: 99% (GLC)

bp

212 °C (lit.)

mp

41-45 °C (lit.)

solubility

water: 20 mg/mL, clear, colorless

density

0.89 g/mL at 25 °C (lit.)

Quality Level

200

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Application

(1R,2S,5R)-(-)-Menthol may be used to synthesize:
  • chiral enantiopure 2-(1-hydroxyalkyl)pyridines, which can react with 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.
Used to prepare reagents for chiral vinylogous Darzens and Reformatsky reactions. Important chiral auxiliary employed in the resolution of acids and for stereocontrolled synthesis.

General description

(1R,2S,5R)-(-)-Menthol is a monoterpene.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBT3378
SHBS7473
SHBS5394
SHBR6556
SHBR4487

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A new 31P NMR method for the enantiomeric excess determination of diols and secondary diamines with C 2 symmetry.
Brunel JM and Faure B.
Tetrahedron Asymmetry, 6(9), 2353-2356 (1995)
Fieser, M.
Reagents for Organic Synthesis, 16, 203-203 (1992)
The Journal of Organic Chemistry, 52, 4397-4397 (1987)
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)
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