Glutaric acid

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). 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. Defects in this metabolic pathway can lead to a disorder called glutaric aciduria, where toxic byproducts build up and can cause severe encephalopathy. 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. 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. Glutaric acid may cause irritation to the skin and eyes.