Pimelic acid

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 interactive 3D 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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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

Synthesis

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.

In other syntheses, pimelic acid is made from cyclohexene-4-carboxylic acid,[3] and a fourth method also exists based on the 1,4 reaction of malonate systems with acrolein.[4]

Patents for the production of pimelic acid have also been reported.[5][6][7][8][9][10] etc.

See also

References

  1. ↑ CRC Handbook of Chemistry and Physics 83rd ed. p.8-52
  2. ↑ "Pimelic Acid". Organic Syntheses 11: 42. 1931. doi:10.15227/orgsyn.011.0042.
  3. ↑ Werber, Frank X.; Jansen, J. E.; Gresham, T. L. (1952). "The Synthesis of Pimelic Acid from Cyclohexene-4-carboxylic Acid and its Derivatives". Journal of the American Chemical Society 74 (2): 532. doi:10.1021/ja01122a075.
  4. ↑ Warner, Donald T.; Moe, Owen A. (1952). "Synthesis of Pimelic Acid and α-Substituted Pimelic Acid and Intermediates1". Journal of the American Chemical Society 74 (2): 371. doi:10.1021/ja01122a024.
  5. ↑ U.S. Patent 2,826,609
  6. ↑ U.S. Patent 2,800,507
  7. ↑ U.S. Patent 2,698,339
  8. ↑ U.S. Patent 3,468,927
  9. ↑ U.S. Patent 4,888,443
  10. ↑ U.S. Patent 2,673,219
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