Glutaric acid
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| Names | |
|---|---|
| Preferred IUPAC name
Pentanedioic acid | |
| Other names
Glutaric acid Propane-1,3-dicarboxylic acid 1,3-Propanedicarboxylic acid Pentanedioic acid n-Pyrotartaric acid | |
| Identifiers | |
110-94-1  | |
| 3D model (Jmol) | Interactive image |
| ChEBI | CHEBI:17859 |
| ChEMBL | ChEMBL1162495 |
| ChemSpider | 723 |
| DrugBank | DB03553 |
| ECHA InfoCard | 100.003.471 |
| EC Number | 203-817-2 |
| KEGG | C00489 |
| PubChem | 743 |
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| Properties | |
| C5H8O4 | |
| Molar mass | 132.12 g/mol |
| Melting point | 95 to 98 °C (203 to 208 °F; 368 to 371 K) |
| Boiling point | 200 °C (392 °F; 473 K) /20 mmHg |
| 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 | |
Glutaric acid is the organic compound with the formula C3H6(COOH)2 . Although the related "linear" dicarboxylic acids adipic and succinic acids are water-soluble only to a few percent at room temperature, the water-solubility of glutaric acid is over 50% (w/w).
Biochemistry
Glutaric acid is naturally produced in the body during the metabolism of some amino acids, including lysine and tryptophan. Defects in this metabolic pathway can lead to a disorder called glutaric aciduria, where toxic byproducts build up and can cause severe encephalopathy.
Production
Glutaric acid can be prepared by the ring-opening of butyrolactone with potassium cyanide to give the mixed potassium carboxylate-nitrile that is hydrolyzed to the diacid.[1] Alternatively hydrolysis, followed by oxidation of dihydropyran gives glutaric acid. It can also be prepared from reacting 1,3-dibromopropane with sodium or potassium cyanide to obtain the dinitrile, followed by hydrolysis.
Uses
- 1,5-Pentanediol, a common plasticizer and precursor to polyesters is manufactured by hydrogenation of glutaric acid and its derivatives.[2]
- Glutaric acid itself has been used in the production of polymers such as polyester polyols, polyamides. The odd number of carbon atoms (i.e. 5) is useful in decreasing polymer elasticity.
- Uvitonic acid is obtained by the action of ammonia on pyrotartaric acid.
Safety
Glutaric acid may cause irritation to the skin and eyes.[3] Acute hazards include the fact that this compound may be harmful by ingestion, inhalation or skin absorption.[3]
References
- ↑ G. Paris, L. Berlinguet, R. Gaudry, J. English, Jr. and J. E. Dayan (1963). "Glutaric Acid and Glutaramide". Org. Synth.; Coll. Vol., 4, p. 496
- ↑ Peter Werle and Marcus Morawietz "Alcohols, Polyhydric" in Ullmann's Encyclopedia of Industrial Chemistry: 2002, Wiley-VCH: Weinheim. DOI 10.1002/14356007.a01_305
- 1 2 Glutaric acid, cameochemicals.com