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formation]] Δfsolidcombustion]] Δcsolid
Oxaloacetic acid
Chemical name Oxobutanedioic acid
Chemical formula C4H4O5
Molecular mass 132.07 g/mol
Melting point 152°C cis, 184°C trans
Density x.xxx g/cm3
pKa value 2.22
3.89
CAS number *
EINECS number 206-329-8
SMILES xxx
Thermodynamic data
Standard enthalpy
of
-943.21 kJ/mol
Standard enthalpy
of
-1205.58 kJ/mol
Chemical infobox

Oxaloacetic acid, also known as oxosuccinic acid or oxalacetic acid, is a four-carbon dicarboxylic acid appearing as an intermediate of the citric acid cycle. In vivo, oxaloacetate (the ionised form of oxaloacetic acid) is formed by the oxidation of L-malate, catalysed by malate dehydrogenase, and reacts with Acetyl-CoA to form citrate, catalysed by citrate synthase. It is also formed in the mesophyll of plants by the condensation of CO2 with phosphoenolpyruvate, catalysed by oxaloacetate decarboxylase. It can be formed from pyruvate as an anaplerotic reaction.

The enol forms of oxaloacetic acid are particularly stable, so much so that the two isomers have different melting points (152°C cis, 184°C trans). The enol proton has a pKa value of 13.02. The enzyme fumarase A from E. coli catalyses the conversion between the keto and enol forms.

Oxaloacetic acid is unstable in solution, decomposing to pyruvic acid by decarboxylation over a period of hours (room temperature) or days (0°C). Refrigerator storage of the solid is recommended for long periods.

External links


Citric acid cycle compounds | Dicarboxylic acids | Ketones

Oxalessigsäure | オキサロ酢酸

 

This article is licensed under the GNU Free Documentation License. It uses material from the "Oxaloacetic acid".

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