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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

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About This Item

Empirical Formula (Hill Notation):
C10H20O
CAS Number:
Molecular Weight:
156.27
Beilstein/REAXYS Number:
1902293
EC Number:
MDL number:
UNSPSC Code:
12352001
PubChem Substance ID:
NACRES:
NA.22

biological source

synthetic (organic)

Quality Level

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.)

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

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

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[2]
  • menthylphosphorodichioridite, a chiral derivatizing agent for the determination of enantiomeric purity of chiral diols or diamines by 31P NMR spectroscopy[3]
  • (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[4]
It may also be used as a chiral auxiliary, to induce chirality while synthesizing (-)-horsfiline.[5]
Used to prepare reagents for chiral vinylogous Darzens and Reformatsky reactions.[6] Important chiral auxiliary employed in the resolution of acids and for stereocontrolled synthesis.[7]

Legal Information

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

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

201.2 °F - closed cup

flash_point_c

94 °C - closed cup


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The Journal of Organic Chemistry, 52, 4397-4397 (1987)
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)
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)

Questions

  1. Good morning. I am interested in the product M2780, (1R,2S,5R)-(−)-Menthol. But I noticed that in the item of "biological source", the information is synthetic (organic). I would like to know what the word organic means here.

    1 answer
    1. The "biological source" entry of "synthetic (organic)" in the properties table for this product indicates that the material is of entirely synthetic origin. The type of chemical synthesis used is organic synthesis, which involves the construction of chemical compounds containing carbon. Definitions for organic compounds often specify the presence of a carbon-carbon or carbon-hydrogen bond.

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