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439061 Sigma-Aldrich

(−)-Isopulegol

99%

Synonym: (1R,2S,5R)-2-Isopropenyl-5-methylcyclohexanol, (1R,3R,4S)-p-Menth-8-en-3-ol

  • CAS Number 89-79-2

  • Empirical Formula (Hill Notation) C10H18O

  • Molecular Weight 154.25

  •  Beilstein/REAXYS Number 1906573

  •  EC Number 201-940-6

  •  MDL number MFCD00134655

  •  PubChem Substance ID 24867323

  •  NACRES NA.22

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Properties

Related Categories Alcohols, Asymmetric Synthesis, Chemical Synthesis, Chiral Building Blocks, Organic Building Blocks More...
Quality Level   100
assay   99%
optical activity   [α]20/D −22°, neat
refractive index   n20/D 1.471 (lit.)
bp   212 °C (lit.)
density   0.912 g/mL at 25 °C (lit.)
SMILES string   C[C@@H]1CC[C@H]([C@H](O)C1)C(C)=C
InChI   1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-11H,1,4-6H2,2-3H3/t8-,9+,10-/m1/s1
InChI key   ZYTMANIQRDEHIO-KXUCPTDWSA-N

Description

General description

Isopulegol is monoterpene alcohol, a useful ingredient for the production of fragrances in perfume industries. It is also used as a starting material in the manufacture of menthol by the hydrogenation process. Menthol is an important component in cosmetics, pharmaceuticals, and toothpaste.

Application

(−)-Isopulegol can be used as a starting material for the enantioselective preparation of:      
•  8-arylmenthols by Smiles-Truce rearrangement of aryl sulfonates.,·        
•  Stereoisomers of 5,9-dimethylpentadecane.
•  Octahydro-2H-chromen-4-ol by Prins cyclization with vanillin in the presence of montmorillonite clay as the catalyst.     
•  p-menthane-3,8,9-triol by catalytic Sharpless dihydroxylation.

Packaging

1 mL in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Target organs 
Respiratory system
RIDADR 
NA 1993 / PGIII
WGK Germany 
WGK 1
Flash Point(F) 
172.4 °F - closed cup
Flash Point(C) 
78 °C - closed cup
Protocols & Articles
Peer-Reviewed Papers
15

References

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