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
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.003.492
EC Number 203-840-8
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[edit]

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]

Several patents exist for the production of pimelic acid.[5][6][7][8][9][10]

See also[edit]

References[edit]

  1. ^ CRC Handbook of Chemistry and Physics 83rd ed. p.8-52
  2. ^ H. R. Snyder, L. A. Brooks, S. H. Shapiro, A. Müller (1931). "Pimelic Acid". Organic Syntheses. 11: 42. doi:10.15227/orgsyn.011.0042.CS1 maint: Uses authors parameter (link)
  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