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Glutaconic acid

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Glutaconic acid
trans
cis
Space-filling model of the trans isomer
Space-filling model of the cis isomer
Names
IUPAC name Pent-2-enedioic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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.

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.

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. Voet, Donald; Voet, Judith G. (2011). Biochemistry (4 ed.). Hoboken, NJ: Wiley. pp. 1040–1041. ISBN 978-0-470-57095-1.
  2. 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. 2006 (18): 3622–3626. doi:10.1002/ejic.200600405.
  3. 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. 1. 146: 146–149. doi:10.1039/P19810000146.
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