Glutaconic acid

Glutaconic acid

trans cis
Names
IUPAC name Pent-2-enedioic acid
Identifiers
CAS Number	628-48-8
3D model (Jmol)	Interactive image
ChEBI	CHEBI:15670
ChEMBL	ChEMBL557347
ChemSpider	4444138
PubChem	5280498
InChI InChI=1S/C5H6O4/c6-4(7)2-1-3-5(8)9/h1-2H,3H2,(H,6,7)(H,8,9)/b2-1+ Key: XVOUMQNXTGKGMA-OWOJBTEDSA-N 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).
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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

1. 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.
2. 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.