Glutaconic acid explained

trans-Glutaconic acid is an organic compound with formula HO₂CCH=CHCH₂CO₂H. This dicarboxylic acid exists as a colorless solid and is related to the saturated chemical glutaric acid, HO₂CC(CH₂)₃CO₂H. Esters and salts of glutaconic acid are called glutaconates.

Glutaconate bound to coenzyme A, glutaconyl-CoA, is an intermediate in lysine metabolism.^[1]

Related compounds

The geometric isomer, cis-glutaconic acid, has a noticeably lower melting point (130–132 °C). It can be prepared by bromination of levulinic acid followed by treatment of the dibromoketone with potassium carbonate.^[2]

Glutaconic anhydride, which forms by dehydration the diacid, exists mainly as the dicarbonyl tautomer in solution. It is a colorless solid melting at 77–82 °C. Either the cis or trans diacid can be used to make it: the trans form isomerizes under the reaction conditions.^[3]

Medical aspects

Glutaric, 3-hydroxyglutaric, and glutaconic acids are structurally related metabolites. In glutaric aciduria type 1, glutaconic acid accumulates, resulting in brain damage.

References

1. Book: Voet, Donald . Biochemistry . Voet . Judith G. . 2011 . Wiley . 978-0-470-57095-1 . 4 . Hoboken, NJ . 10401041.
2. Buckel, W.. Pierik, A. J.. Plett, S.. Alhapel, A.. Suarez, D.. Tu, S.-m.. Golding, B. T. . Mechanism-Based Inactivation of Coenzyme B₁₂-Dependent 2-Methyleneglutarate Mutase by (Z)-Glutaconate and Buta-1,3-diene-2,3-dicarboxylate . Eur. J. Inorg. Chem. . 2006 . 2006 . 18 . 3622–3626 . 10.1002/ejic.200600405.
3. Briggs, S. P.. Davies, D. I.. Newton, R. F.. Reynolds, D. P. . The Structure of Glutaconic Anhydride and the Synthetic Utility of its Diels–Alder Adduct with Cyclopentadiene . 146 . J. Chem. Soc. Perkin Trans. 1 . 1981 . 146–149 . 10.1039/P19810000146.