Oxalacetic acid

Base Information

• Chemical Name: Oxalacetic acid
• CAS No.: 328-42-7
• Molecular Formula: C4H4O5
• Molecular Weight: 132.073
• Hs Code.: 29183000
• European Community (EC) Number: 206-329-8
• NSC Number: 77688
• UNII: 2F399MM81J
• DSSTox Substance ID: DTXSID8021646
• Nikkaji Number: J5.675H
• Wikipedia: Oxaloacetic_acid
• Wikidata: Q408658
• NCI Thesaurus Code: C168687
• Metabolomics Workbench ID: 2032
• ChEMBL ID: CHEMBL1794791
• Mol file: 328-42-7.mol

Synonyms:2 Ketosuccinic Acid;2 oxo Butanedioic Acid;2-Ketosuccinic Acid;2-oxo-Butanedioic Acid;Acid, Oxalacetic;Acid, Oxaloacetic;Ketosuccinic Acid;Oxalacetic Acid;Oxaloacetate;Oxaloacetic Acid

Chemical Property of Oxalacetic acid

Chemical Property:

• Appearance/Colour: off-white crystals
• Vapor Pressure: 1.41E-05mmHg at 25°C
• Melting Point: 161 °C (dec.)(lit.)
• Refractive Index: 1.4000 (estimate)
• Boiling Point: 341.931 °C at 760 mmHg
• PKA: 2.22(at 25℃)
• Flash Point: 174.794 °C
• PSA: 91.67000
• Density: 1.632 g/cm³
• LogP: -0.88520
• Storage Temp.: −20°C
• Solubility.: H2O: 100 mg/mL
• Water Solubility.: soluble
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 132.00587322
• Heavy Atom Count: 9
• Complexity: 158

Purity/Quality:

99.9% ^*data from raw suppliers

Oxaloacetic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C(C(=O)C(=O)O)C(=O)O
• Recent ClinicalTrials: Pharmacodynamic Analyses of Metabolic Agents Following Brain Radiation
• 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.
• Uses: A four carbon dicarboxylic acid that is an intermediate in the citric acid cycle and glucogenesis. It has been shown to inhibit succinate dehydrogenase. Use as a TCA (Krebs cycle) intermediate supplement in hybridoma cell culture applications. Enhances hybridoma growth and productivity. 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.

Technology Process of Oxalacetic acid

There total 63 articles about Oxalacetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

Acetylenedicarboxylic acid (142-45-0) → Oxalacetic acid (328-42-7)

Guidance literature:

With water; di[triaqua{2,6-di(phenylthiomethyl)pyridine}ruthenium(III)] tri-sulphate; at 80 ℃; for 12h; pH=2.0; Product distribution / selectivity;

Reference yield: 58.0%

malic acid (617-48-1,78644-42-5) → Oxalacetic acid (328-42-7) + malonic acid (141-82-2) + oxalic acid (144-62-7,97993-78-7)

Guidance literature:

With iron disulphate; dihydrogen peroxide; at 2 ℃;

DOI:10.1039/c9gc01768b

Reference yield: 15.5%

citric acid (77-92-9,906507-37-7) → Oxalacetic acid (328-42-7) + L-Lactic acid (79-33-4,106989-11-1,26811-96-1,31587-11-8,26100-51-6) + D-Lactic acid (10326-41-7,106989-11-1,26811-96-1,31587-11-8,26100-51-6) + 3-hydroxy-2-butanon (513-86-0,52217-02-4,51555-24-9) + acetic acid (64-19-7,77671-22-8) + 2-oxo-propionic acid (127-17-3)

Guidance literature:

With Leuconostoc mesenteroides; at 30 ℃; for 1h; potassium phosphate buffer, pH 5.0; other conditions also investigated; several substrates investigated;

upstream raw materials:

(S)-Malic acid

3,7-bis(dimethylamine)phenothiazonium

malic acid

phosphoenolpyruvic acid

Downstream raw materials:

L-Aspartic acid

N-Acetylneuraminic acid

ketomalonic acid phenylhydrazone

5-oxo-2,5-dihydro-1H-pyrazole-3-carboxylic acid

Refernces

Synthesis and identification in bacterial lipopolysaccharides of 5,7-diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-galacto- and -D-glycero-D-talo-non-2-ulosonic acids

10.1016/S0008-6215(01)00041-6

The study focused on the synthesis and identification of specific non-2-ulosonic acids, namely 5,7-diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-galacto- and -D-glycero-D-talo-non-2-ulosonic acids, which are components of bacterial lipopolysaccharides (LPS). These compounds play a crucial role in the serological specificity of gram-negative bacteria and contribute to the bacterial surface's physicochemical properties. The chemicals used in the study included 2,4-diacetamido-2,4,6-trideoxy-D-mannose, oxalacetic acid, and sodium tetraborate. These were utilized in the condensation process to synthesize the target non-2-ulosonic acids. The study's purpose was to unambiguously identify these higher sugars, determine their absolute configuration, and differentiate them from their L-glycero-D-galacto and L-glycero-D-talo isomers, which were previously synthesized. This was achieved through the comparison of 1H and 13C NMR data, specific optical rotation values, and the analysis of natural compounds, enabling the identification of derivatives of 5,7-diamino-3,5,7,9-tetradeoxy-D-glycero-D-galacto-non-2-ulosonic acid (legionaminic acid) and its epimers in bacterial LPS.