Glutaconic acid

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C5H6O4/c6-4(7)2-1-3-5(8)9/h1-2H,3H2,(H,6,7)(H,8,9)/b2-1+ checkY
    Key: XVOUMQNXTGKGMA-OWOJBTEDSA-N checkY
  • 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
  • O=C(O)\C=C\CC(=O)O
Properties
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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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 dehydrating 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]

Glutaconaldehyde is the corresponding dialdehyde.

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

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