trans-Glutaconic acid is an organic compound with formula HO<sub>2</sub>CCH=CHCH<sub>2</sub>CO<sub>2</sub>H. This dicarboxylic acid exists as a colorless solid and is related to the saturated chemical glutaric acid, HO<sub>2</sub>CC(CH<sub>2</sub>)<sub>3</sub>CO<sub>2</sub>H. Esters and salts of glutaconic acid are called glutaconates.
Glutaconate bound to coenzyme A, glutaconyl-CoA, is an intermediate in lysine metabolism.
The geometric isomer, cis-glutaconic acid, has a noticeably lower melting point (130âÂÂ132 ðC). It can be prepared by bromination of levulinic acid followed by treatment of the dibromoketone with potassium carbonate.
Glutaconic anhydride, which forms by dehydration the diacid, exists mainly as the dicarbonyl tautomer in solution. It is a colorless solid melting at 77âÂÂ82 ðC. Either the cis or trans diacid can be used to make it: the trans form isomerizes under the reaction conditions.
Glutaric, 3-hydroxyglutaric, and glutaconic acids are structurally related metabolites. In glutaric aciduria type 1, glutaconic acid accumulates, resulting in brain damage.