Formula C7H12O4 Density 1.28 g/cm³ | Molar mass 160.17 g/mol | |
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Pimelic acid is the organic compound with the formula HO2C(CH2)5CO2H. Derivatives of pimelic acid are involved in the biosynthesis of the amino acid called lysine. Pimelic acid is one CH
2 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 (not IUPAC) 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.
Patents for the production of pimelic acid have also been reported. etc.