Pimelic acid
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.
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| IUPAC name
heptanedioic acid | |
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| ECHA InfoCard | 100.003.492  |
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| 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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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]
Several patents exist for the production of pimelic acid.[5][6][7][8][9][10]
See also
References
- CRC Handbook of Chemistry and Physics 83rd ed. p.8-52
- 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)
- 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.
- 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.
- U.S. Patent 2,826,609
- U.S. Patent 2,800,507
- U.S. Patent 2,698,339
- U.S. Patent 3,468,927
- U.S. Patent 4,888,443
- U.S. Patent 2,673,219
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