Pimelic acid

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Pimelic acid
Skeletal formula of pimelic acid
Ball-and-stick model of the pimelic acid molecule
Names
IUPAC name
heptanedioic acid
Identifiers
111-16-0 YesY
ChEBI CHEBI:30531 N
ChemSpider 376 N
DrugBank DB01856 N
EC number 203-840-8
Jmol-3D images Image
PubChem 385
Properties
C7H12O4
Molar mass 160.17 g/mol
Density 1.28 g/cm3
Melting point 103 to 105 °C (217 to 221 °F; 376 to 378 K)
Boiling point decomposes
Acidity (pKa) 4.71 pKa2 = 5.58 [1]
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
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 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

Pimelic acid has been synthesized from cyclohexanone and from salicylic acid.[2] In the former route, the additional carbon is supplied by dimethyloxalate, which reacts with the enolate.

See also[edit]

References[edit]

  1. ^ CRC Handbook of Chemistry and Physics 83rd ed. p.8-52
  2. ^ 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