89-79-2

  • Product Name:ISOPULEGOL
  • Molecular Formula:C10H18 O
  • Purity:99%
  • Molecular Weight:
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Product Details;

CasNo: 89-79-2

Molecular Formula: C10H18 O

89-79-2 Name

Name

ISOPULEGOL

Synonym

5-methyl-2-(1-methylethenyl)-,[1R-(1.alpha.,2.beta.,5.alpha.)]-Cyclohexanol;(-)-Isopulegol 99%;Isopulegol solution;(-)-ISOPULEGOL, TERPENE STANDARD;(-)-ISOPULEGOL 95+%;ISOPULEGOL 99+%;(-)-ISOPULEGOL;ISOPULEGOL

 

89-79-2 Biological Activity

Description

(-)-Isopulegol is prepared directly from the treatment of essential oil of citronella under solid supported acid catalysis and solvent-free microwave assisted ene-cyclisation. (-)-Isopulegol shows high activity in reacting with carbonyl compounds. (-)-Isopulegol can be used for antiviral activity research[1].

Related Catalog

Research Areas >> Infection

Signaling Pathways >> Others >> Others

References

[1]. Raquel G.Jacob, et al. Green synthesis of (−)-isopulegol from (+)-citronellal: application to essential oil of citronella. Tetrahedron Letters. 2003 April 28;44(18):3605-3608.

[2]. Ilyina IV, et al. Highly potent activity of isopulegol-derived substituted octahydro-2H-chromen-4-ols against influenza A and B viruses. Bioorg Med Chem Lett. 2018 Jun 15;28(11):2061-2067.

 

89-79-2 Chemical & Physical Properties

Melting point 

78°C

Boiling point

212 °C(lit.)

Density

0.912 g/mL at 25 °C(lit.)

Molecular Formula

C10H18O

Molecular Weight

154.24900

Flash Point

195 °F

PSA

20.23000

LogP

2.35960

Exact Mass

154.13600

Index of Refraction

n20/D 1.471(lit.)

Storage condition

-20°C

 

89-79-2 Description

(–)-Isopulegol is a monoterpene that has been found in the essential oils of several aromatic plants, including Cannabis, with diverse biological activities. It has antibacterial activity against S. aureus, E. faecium, E. coli, and M. smegmatis (MICs = 0.78, 12.5, 0.78, and 1.56 μl/ml, respectively, in an agar diffusion assay) and antifungal activity against C. albicans and A. niger (MIC = 1.56 μl/ml for both in an agar diffusion assay). (–)-Isopulegol inhibits C. albicans morphogenesis, adhesion, and biofilm formation (MICs = 0.125, 4, and 0.25 mg/ml, respectively). In vivo, (–)-isopulegol (50 mg/kg, i.p.) increases immobility time in the forced swim and tail suspension tests and increases the number of head dips in a hole board test and time spent in the open arms of the elevated plus maze in mice, indicating depressant- and anxiolytic-like activity. It reduces the size of ulcerated lesions in the stomach in mouse models of ethanol- and indomethacin-induced gastric lesions when administered at a dose of 100 mg/kg.

 

89-79-2 Uses

(-)-Isopulegol can be used as a starting material for the enantioselective preparation of:

  1. 8-arylmenthols by Smiles-Truce rearrangement of aryl sulfonates.,
  2. Stereoisomers of 5,9-dimethylpentadecane.
  3. Octahydro-2H-chromen-4-ol by Prins cyclization with vanillin in the presence of montmorillonite clay as the catalyst.
  4. p-menthane-3,8,9-triol by catalytic Sharpless dihydroxylation.

 

 

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