Pimelic acid

Pimelic acid
IUPAC name

heptanedioic acid
Identifiers
CAS number 111-16-0 Y
Jmol-3D images Image 1
Properties
Molecular formula C7H12O4
Molar mass 160.17 g/mol
Density 1.28 g/cm3
Melting point

103–105 °C
Boiling point

Decomposes
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 methylene 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

Pimelic acid has been synthesized from cyclohexanone and from salicylic acid.[1] In the former route, the additional carbon is supplied by dimethyloxalate, which reacts with the enolate.

See also

References

  1. ^ Snyder, H. R.; Brooks, A. L.; Shapiro, S. H. "Pimelic Acid from Cyclohexanone" and Müller, A. "Pimelic Acid from Salicylic Acid" Organic Syntheses, Collected Volume 2, p.531 (1943).http://www.orgsyn.org/orgsyn/pdfs/CV2P0531.pdf