Glutaconic acid

trans

cis

Names

IUPAC name

Pent-2-enedioic acid

Identifiers

628-48-8^N

CHEBI:15670^Y

4444138^Y

Jmol interactive 3D

InChI=1S/C5H6O4/c6-4(7)2-1-3-5(8)9/h1-2H,3H2,(H,6,7)(H,8,9)/b2-1+^Y
Key: XVOUMQNXTGKGMA-OWOJBTEDSA-N^Y
InChI=1/C5H6O4/c6-4(7)2-1-3-5(8)9/h1-2H,3H2,(H,6,7)(H,8,9)/b2-1+
Key: XVOUMQNXTGKGMA-OWOJBTEDBR

SMILES

O=C(O)\C=C\CC(=O)O

Properties

Chemical formula

C₅H₆O₄

Molar mass

130.099 g/mol

Appearance

Colorless solid

Melting point

137 to 139 °C (279 to 282 °F; 410 to 412 K)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

verify (what is ^YN ?)

Infobox references

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.

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.^[1]

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.^[2]

Medical aspects

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

References

↑ Buckel, W.;Pierik, A. J.; Plett, S.; Alhapel, A.; Suarez, D.; Tu, S.-m.; Golding, B. T. (2006). "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. (18): 3622–3626. doi:10.1002/ejic.200600405.
↑ Briggs, S. P.; Davies, D. I.; Newton, R. F.; Reynolds, D. P. (1981). "The Structure of Glutaconic Anhydride and the Synthetic Utility of its Diels–Alder Adduct with Cyclopentadiene". J. Chem. Soc. Perkin Trans I 146: 146–149. doi:10.1039/P19810000146.

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