89-79-2

(–)-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.

Synthesis: Several stereoisomers are possible; only l-isopulegol and d-α-isopulegol have been isolated from mixtures of alcohols obtained by cyclization of d-citronellal.

Isopulegol is a cyclic nonaromatic alcohol.

Water-white liquid; mint-like odor. Combustible. Available forms: The acetate.

l-Isopulegol has been reported found in the essences of lemongrass, East African geranium and Eucalyptus citriodora; d-isopulegol is present in the oils of Backhousia and Baeckea citriodorae; d-neoisopulegol is found in Mentha rotundifolia. Also reported found in mint, mandarin, orange juice, citrus peel oils, currant bud, ginger, corn mint oil, cognac, rum, buchu oil, lemon balm and mastic gum oil

ChEBI: A natural product found in Citrus hystrix.

Several stereoisomers are possible; only l-isopulegol and d-α-isopulegol have been isolated from mixtures of alcohols obtained by cyclization of d-citronellal.

Detection: 1 ppm

Taste characteristics at 30 ppm: minty cooling, herbaceous peppermint nuance.

Synthetic Communications, 18, p. 2309, 1988 DOI: 10.1080/00397918808082375

Nonflammable

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