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15785 Sigma-Aldrich

(−)-Menthol

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

Synonym: (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol, 5-Methyl-2-(1-methylethyl)cyclohexanol

  • CAS Number 2216-51-5

  • Empirical Formula (Hill Notation) C10H20O

  • Molecular Weight 156.27

  •  Beilstein/REAXYS Number 1902293

  •  EC Number 218-690-9

  •  MDL number MFCD00062979

  •  PubChem Substance ID 57647522

  •  NACRES NA.22

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Properties

Related Categories Alcohols, Analytical/Chromatography, Asymmetric Synthesis, Cell Biology, Chemical Synthesis,
Quality Level   200
grade   puriss.
assay   98.0-102.0%
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
Featured Industry   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

Description

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.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 1
RTECS 
OT0700000
Flash Point(F) 
213.8 °F - closed cup
Flash Point(C) 
101 °C - closed cup

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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