Piperonyl acetone

Description

4-(3,4-Methylenedioxyphenyl)-2-butanone has an intensely sweet, floral, slightly woody odor. May be prepared by condensation of heliotropin with acetone, followed by hydrogenation in the presence of a palladium catalyst.

Chemical properties

4-(3,4-Methylenedioxyphenyl)-2-butanone has an intensely sweet, floral, slightly woody odor reminiscent of raspberry, cotton candy (i.e., candy floss) with a cassie, heliotrope association.

Occurrence

Has apparently not been reported to occur in nature.

Definition

ChEBI: 4-(3,4-Methylenedioxyphenyl)-2-butanone is a member of benzodioxoles.

Preparation

By condensation of heliotropin with acetone, followed by hydrogenation in the presence of a palladium catalyst

Taste threshold values

Taste characteristics at 40 ppm: sweet, berry-like with spicy, jamy nuances

Metabolism

The oxygen-aromatic carbon link of aromatic ethers is generally biologically stable, and possible metabolites include the p-hydroxy derivative of the ether, the phenol or the p-hydroxyphenol (Williams, 1959). Ketones are not readily metabolized in the body. As a derivative of 2-butanone, piperonyl acetone might be expected to be partially reduced to the secondary alcohol and excreted as the glucuronide (Williams, 1959), since Saneyoshi (1911) isolated the glucuronide of 2-butanol from the urine of rabbits receiving methyl ethyl ketone.