Oxobutanedioic acid

Description

Oxaloacetic acid is an α-keto acid and a key component of cellular metabolism in its conjugate base form, oxaloacetate. Oxaloacetate reacts with acetyl-coenzyme A (acetyl-CoA; ) and water to form citrate in the first step of the citric acid cycle and is regenerated by oxidation of L-malate in the final step. It is an intermediate in gluconeogenesis that is formed in mitochondria via carboxylation of pyruvate and subsequently decarboxylated and phosphorylated to form phosphoenolpyruvate. It can be converted to aspartate via addition of an amino group from glutamate. Oxaloacetate (30 μmol/min per 100 g for 30 minutes, i.v.) reduces blood glutamate levels, severity of neurological dysfunction, and brain edema in a rat model of closed head injury.

Chemical properties

off-white crystals

The Uses of Oxobutanedioic acid

A four carbon dicarboxylic acid that is an intermediate in the citric acid cycle and glucogenesis. It has been shown to inhibit succinate dehydrogenase.

The Uses of Oxobutanedioic acid

Oxaloacetic acid is a substrate for malate dehydrogenase and oxaloacetate decarboxylase. It is an inhibitor of succinic dehydrogenase. It is an intermediate in the citric acid cycle and glucogenesis.

The Uses of Oxobutanedioic acid

Use as a TCA (Krebs cycle) intermediate supplement in hybridoma cell culture applications. Enhances hybridoma growth and productivity.

What are the applications of Application

Oxaloacetic Acid is a malate dehydrogenase and oxaloacetate decarboxylase substrate

Definition

ChEBI: An oxodicarboxylic acid that is succinic acid bearing a single oxo group.

General Description

Oxaloacetic acid is a dicarboxylic acid. It is an intermediate in the citric acid cycle. It is highly soluble in water and is present ubiquitously. It is produced in the mitochondria by the action of pyruvate carboxylase on pyruvate. Breakdown products of oxaloacetate includes malate, pyruvate and aspartic acid.

Flammability and Explosibility

Not classified

Biological Activity

Oxalacetic acid (Oxaloacetic acid, 2-Oxosuccinic acid, Ketosuccinic acid) is an intermediate of the citric acid cycle, where it reacts with acetyl-CoA to form citrate, catalysed by citrate synthase. It is also involved in gluconeogenesis, urea cycle, glyoxylate cycle, amino acid synthesis, and fatty acid synthesis. Oxaloacetate is also a potent inhibitor of Complex II.

Biochem/physiol Actions

Oxaloacetic acid being an intermediate in the tri carboxylic cycle is central to metabolism. It is part of gluconeogenesis pathway. Mutation in pyruvate carboxylase leads to decreased production of oxaloacetate. It inhibits succinate dehydrogenase and is a key regulator of mitochondrial metabolism.

Purification Methods

Crystallise it from boiling EtOAc, or from hot Me2CO/hot *C6H6. [Beilstein 3 IV 1808.]