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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:
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

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P1386W2924008.00605
Propionic acid BioReagent, suitable for insect cell culture, ~99%

P5561

Propionic acid

Propionic acid ≥99.5%

P1386

Propionic acid

Propionic acid ≥99.5%, FCC, FG

W292400

Propionic acid

Propionic acid for synthesis

8.00605

Propionic acid

Quality Level

100

Quality Level

200

Quality Level

400

Quality Level

200

solubility

H2O: soluble

solubility

-

solubility

H2O: soluble

solubility

-

mp

−24-−23 °C (lit.)

mp

−24-−23 °C (lit.)

mp

−24-−23 °C (lit.)

mp

-20 °C

bp

141 °C (lit.)

bp

141 °C (lit.)

bp

141 °C (lit.)

bp

140.7-141.4 °C/1013 hPa

refractive index

n20/D 1.386 (lit.)

refractive index

n20/D 1.386 (lit.)

refractive index

n20/D 1.386 (lit.)

refractive index

-

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
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

  • Specification Sheet

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    Certificates of Analysis (COA)

    Lot/Batch Number
    SLCK5145
    SHBL7914
    SLBZ4571
    MKBM0320V
    MKCB6080

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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)
    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

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