3-Maleylpyruvic acid

3-Maleylpyruvic acid
Names
Preferred IUPAC name
(2Z)-4,6-Dioxohept-2-enedioic acid
Identifiers
3D model (JSmol)
1725756
ChEBI
ChemSpider
KEGG
  • InChI=1S/C7H6O6/c8-4(1-2-6(10)11)3-5(9)7(12)13/h1-2H,3H2,(H,10,11)(H,12,13)/b2-1-
    Key: AZCFLHZUFANAOR-UPHRSURJSA-N
  • C(C(=O)/C=C\C(=O)O)C(=O)C(=O)O
Properties
C7H6O6
Molar mass 186.119 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

3-Maleylpyruvic acid, or 3-maleylpyruvate, is a dicarboxylic acid formed by the oxidative ring opening of gentisic acid by gentisate 1,2-dioxygenase during the metabolism of tyrosine.[1] It is converted into 3-fumarylpyruvate by maleylpyruvate isomerase.[2]

  1. ^ Sugiyama S, Yano K, Komagata K, Arima K (1960). "Metabolites of aromatic compounds by microbes. Part VII. Gentisic acid oxidase". Bull. Agric. Chem. Soc. Jpn. 24: 243–248.
  2. ^ Lack L (1961). "Enzymic cis-trans isomerization of maleylpyruvic acid". J. Biol. Chem. 236 (11): 2835–2840. doi:10.1016/S0021-9258(19)76386-8. PMID 14461395.