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'''Pimelic acid''' is the ] with the ] HO<sub>2</sub>C(CH<sub>2</sub>)<sub>5</sub>CO<sub>2</sub>H. Derivatives of pimelic acid are involved in the biosynthesis of the ] called ]. Pimelic acid is one methylene longer than a related ], 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: ] '''Pimelic acid''' is the ] with the ] HO<sub>2</sub>C(CH<sub>2</sub>)<sub>5</sub>CO<sub>2</sub>H. Derivatives of pimelic acid are involved in the biosynthesis of the ] called ]. Pimelic acid is one ] longer than a related ], 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: ]


Pimelic acid has been synthesized from ] and from ].<ref>Snyder, H. R.; Brooks, A. L.; Shapiro, S. H. "Pimelic Acid from Cyclohexanone" and Müller, A. "Pimelic Acid from Salicylic Acid" Pimelic acid has been synthesized from ] and from ].<ref>Snyder, H. R.; Brooks, A. L.; Shapiro, S. H. "Pimelic Acid from Cyclohexanone" and Müller, A. "Pimelic Acid from Salicylic Acid"

Revision as of 14:43, 30 August 2011

Pimelic acid
Pimelic acid
Names
IUPAC name heptanedioic acid
Identifiers
CAS Number
3D model (JSmol)
ECHA InfoCard 100.003.492 Edit this at Wikidata
CompTox Dashboard (EPA)
SMILES
  • OC(=O)CCCCCC(=O)O
Properties
Chemical formula C7H12O4
Molar mass 160.17 g/mol
Density 1.28 g/cm
Melting point 103-105 °C
Boiling point Decomposes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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. 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
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