Geranylacetone
# Geranylacetone

Geranylacetone is an organic compound with the formula $CH_3C(O)(CH_2)_2CH=C(CH_3)(CH_2)_2CH=C(CH_3)_2.$ A colorless oil, it is the product of coupling geranyl and acetonyl groups. It is a precursor to synthetic squalene.

## Synthesis and occurrence

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

    $EtOC(O)CH_2C(O)CH_3$ + $C_{10}H_{17}OH$ → $C_{10}H_{17}OC(O)CH_2C(O)CH_3$ + 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.

## Biosynthesis

It arises by the oxidation of certain carotenoids. Such reaction are catalyzed by carotenoid oxygenase.

