Computational Analysis of Glycerol Menthonide Using Spartan ’04

Glycerol menthonide has been reported in the literature and has been prepared by reaction of menthone with glycerol under acid catalysis. The menthonide was originally prepared as an additive to spearmint gum by a chemist at Wrigley’s Inc. No further chemical analysis of the menthonide has been reported in the literature. However, glycerol menthonide should be a mixture of up to 6 isomers. Spartan ‘04 was used to determine the heat of formation of each isomer in an attempt to model the reaction mixture. This information was then compared with GC/MS analysis of the product mixture. The isolation of one of the stereoisomers of glycerol menthonide is also reported.