CAS 491-02-1: neoisomenthol

Neoisomenthol is a chiral compound that inhibits the growth of oral pathogens. It has been shown to have low energy and high solubility in organic solvents, which leads to its use as a catalyst in pharmaceutical preparations. Neoisomenthol also exhibits in vitro antifungal activity against Candida albicans and Saccharomyces cerevisiae. This compound is an analog of menthol and is synthesized by reacting cyclohexane with an aryl halide. It can be extracted from the essential oil of peppermint or synthesized chemically. Neoisomenthol has been shown to inhibit the synthesis of isovaleric acid by inhibiting the activity of acetyl-CoA carboxylase enzyme.

Applications (±)-Neoisomenthol is a useful synthetic intermediate. It is used to prepare alkyl and aryl esters by chemoselective acylation of alkyl and aryl alcohols with carboxylic acid anhydrides in the presence of magnesium bis(trifluoromethylsulfonyl)amide under solvent-free conditions. References Chakraborti, A., et al.: J. Org. Chem., 71, 5785 (2006)