Glutaric acid
Chemical compound
From Wikipedia, the free encyclopedia
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). [citation needed]
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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 | |
| ECHA InfoCard | 100.003.471 |
| EC Number |
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| 26809 | |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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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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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]