Geranylacetone

Synthesis and occurrence

Geranylacetone can be produced by transesterification of ethyl acetoacetate with linalool:

EtOC(O)CH₂C(O)CH₃ + C₁₀H₁₇OH → C₁₀H₁₇OC(O)CH₂C(O)CH₃ + EtOH

The esterification of linalool can also be effected with ketene or isopropenyl methyl ether. The resulting linalyl ester undergoes Carroll rearrangement to give geranylacetone. Geranyl acetone is a precursor to isophytol, which is used in the manufacture of Vitamin E. Other derivatives of geranyl acetone are farnesol and nerolidol.

Geranylacetone is a flavor component of many plants including rice, mango, and tomatoes.

Together with other ketones, geranylacetone results from the degradation of vegetable matter by ozone.