Pimelic acid is the organic compound with the formulaHO2C(CH2)5CO2H. Pimelic acid is one CH
2 unit longer than a related dicarboxylic acid, adipic acid, a precursor to many polyesters and polyamides. However compared to adipic acid, pimelic acid is relatively small in importance industrially.[2] Derivatives of pimelic acid are involved in the biosynthesis of the amino acid lysine and the vitamin biotin.
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| Preferred IUPAC name
Heptanedioic acid | |
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| ECHA InfoCard | 100.003.492 
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CompTox Dashboard (EPA) |
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| Properties | |
| C7H12O4 | |
| Molar mass | 160.17 g/mol |
| Appearance | colorless or white solid |
| 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). | |
The biosynthesis of pimelic acid is unknown but is speculated to start with malonyl CoA.[3]
Like other simple dicarboxylic acids, many methods have been developed for producing pimelic acid. Pimelic acid is produced commercially by oxidation of cycloheptanone with dinitrogen tetroxide. Other routes include the relatively unselective oxidation of palmitic acid and the carbonylationofcaprolactone.[2]
Many other methods exist. Pimelic acid has been synthesized from cyclohexanone and from salicylic acid.[4] 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,[5] and a fourth method also exists based on the 1,4 reaction of malonate systems with acrolein.[6]
Several patents exist for the production of pimelic acid.[7][8][9][10][11][12]
