Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

M2780

Sigma-Aldrich

(1R,2S,5R)-(−)-Menthol

ReagentPlus®, 99%

Synonym(s):

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

Sign Into View Organizational & Contract Pricing

Select a Size

All Photos(3)

Select a Size

Change View

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:
24896767
NACRES:
NA.22

biological source

synthetic (organic)

Quality Level

200

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

General description

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

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.

Legal Information

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

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SLCK5145
SHBL7914
SLBZ4571
MKBM0320V
MKCB6080

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
The Journal of Organic Chemistry, 52, 4397-4397 (1987)
Fieser, M.
Reagents for Organic Synthesis, 16, 203-203 (1992)
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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service