Pimelic acid


Pimelic acid is the organic compound with the formula HO2C5CO2H. Derivatives of pimelic acid are involved in the biosynthesis of the amino acid called lysine. Pimelic acid is one unit longer than a related dicarboxylic acid, adipic acid, a precursor to many polyesters and polyamides. It is the final member of the mnemonic used to aid recollection of the order of the first six dicarboxylic acids using their common nomenclature: Dicarboxylic acid

Synthesis

Pimelic acid has been synthesized from cyclohexanone and from salicylic acid. 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, and a fourth method also exists based on the 1,4 reaction of malonate systems with acrolein.
Several patents exist for the production of pimelic acid.