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| Names | |
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| Preferred IUPAC name Heptanedioic acid | |
| Identifiers | |
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3D model (JSmol) | |
| ChEBI | |
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| DrugBank |
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| ECHA InfoCard | 100.003.492 |
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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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Pimelic acid is theorganic compound with theformula HO2C(CH2)5CO2H. Pimelic acid is oneCH
2 unit longer than a relateddicarboxylic 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 theamino acidlysine and the vitaminbiotin.
The biosynthesis of pimelic acid is unknown but is speculated to start withmalonyl CoA.[3]
Like other simpledicarboxylic acids, many methods have been developed for producing pimelic acid.Pimelic acid is produced commercially by oxidation ofcycloheptanone withdinitrogen tetroxide. Other routes include the relatively unselective oxidation ofpalmitic acid and thecarbonylation ofcaprolactone.[2]
Many other methods exist. Pimelic acid has been synthesized fromcyclohexanone and fromsalicylic 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 withacrolein.[6]
Several patents exist for the production of pimelic acid.[7][8][9][10][11][12]
| Authority control databases: National |
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