Chemistry:Glutaric acid
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| Names | |
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| Preferred IUPAC name
Pentanedioic acid | |
| Other names
Glutaric acid
Propane-1,3-dicarboxylic acid 1,3-Propanedicarboxylic acid Pentanedioic acid n-Pyrotartaric acid 1,5-Pentanedioic acid | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| EC Number |
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| 26809 | |
| KEGG | |
PubChem CID
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| UNII | |
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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). | |
 verify (what is   ?)
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| Infobox references | |
Biochemistry
Glutaric acid is naturally produced in the body during the metabolism of some amino acids, including lysine and tryptophan. It can also arise by chain extension of α-ketoglutarate to α-ketoadipate.[1]
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 potassium salt of the carboxylate-nitrile that is hydrolyzed to the diacid.[2] 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. Using periodate, it is obtained from oxidation of 1,3-cyclohexanedione, which proceeds with decarboxylation.[3]
Uses
- 1,5-Pentanediol, a common plasticizer and precursor to polyesters is manufactured by hydrogenation of glutaric acid and its derivatives.[4]
- 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.[5]
- Pyrogallol can be produced from glutaric diester.[6]
Safety
Glutaric acid may cause irritation to the skin and eyes.[7] Acute hazards include the fact that this compound may be harmful by ingestion, inhalation or skin absorption.[7]
References
- ↑ Wang, Jian; Wu, Yifei; Sun, Xinxiao; Yuan, Qipeng; Yan, Yajun (2017). "De Novo Biosynthesis of Glutarate via α-Keto Acid Carbon Chain Extension and Decarboxylation Pathway in Escherichia coli". ACS Synthetic Biology 6 (10): 1922–1930. doi:10.1021/acssynbio.7b00136. PMID 28618222.
- ↑ G. Paris, L. Berlinguet, R. Gaudry, J. English, Jr. and J. E. Dayan (1957). "Glutaric Acid and Glutaramide". Organic Syntheses: 47. doi:10.15227/orgsyn.037.0047.
- ↑ Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, p. 1736, ISBN 978-0-471-72091-1, https://books.google.com/books?id=JDR-nZpojeEC&printsec=frontcover
- ↑ Peter Werle and Marcus Morawietz "Alcohols, Polyhydric" in Ullmann's Encyclopedia of Industrial Chemistry: 2002, Wiley-VCH: Weinheim. DOI 10.1002/14356007.a01_305
- ↑ "Glutaric acid, Pentanedioic acid, 99%" (in en-us). http://www.chemkits.eu/carboxylic-acids/232-glutaric-acid-pentanedioic-acid-110-94-1.html.
- ↑ Shipchandler, Mohammed T., "Method of synthesis of pyrogallol", US patent 4046817, published 1977-09-06
- ↑ 7.0 7.1 Glutaric acid, cameochemicals.com
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