Pimelic acid

The biosynthesis of pimelic acid is unknown but is speculated to start with malonyl CoA.

Pimelic acid is produced commercially by oxidation of cycloheptanone with dinitrogen tetroxide.

Other routes include the relatively unselective oxidation of palmitic acid and the carbonylation of caprolactone.

[4] In the former route, the additional carbon is supplied by dimethyloxalate, which reacts with the enolate.

In other syntheses, pimelic acid is made from cyclohexene-4-carboxylic acid,[5] and a fourth method also exists based on the 1,4 reaction of malonate systems with acrolein.

Skeletal formula of pimelic acid
Ball-and-stick model of the pimelic acid molecule