Pimelic acid
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| Pimelic acid | ||
|---|---|---|
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| IUPAC name heptanedioic acid | ||
| Identifiers | ||
| CAS number | 111-16-0  | |
| DrugBank | DB01856 | |
| Jmol-3D images | Image 1 | |
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| Properties | ||
| Molecular formula | C7H12O4 | |
| Molar mass | 160.17 g/mol | |
| Density | 1.28 g/cm3 | |
| Melting point | 103–105 °C | |
| Boiling point | Decomposes | |
| Acidity (pKa) | 4.71 pKa2 = 5.58 [1] | |
(verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | ||
| 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
References
- ↑ CRC Handbook of Chemistry and Physics 83rd ed. p.8-52
- ↑ 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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