Oxaloacetic acid
Chemical name	Oxobutanedioic acid
Other names	Oxaloacetic acid Oxalacetic acid Oxosuccinic acid
Chemical formula	C4H4O5
Molecular mass	132.07 g/mol
Melting point	161 °C
Density	? g/cm3
pKa value	2.22 3.89
CAS number	[328-42-7]
EINECS number	206-329-8
SMILES	OC(C(CC(O)=O)=O)=O
Thermodynamic data
Standard enthalpy of formation ΔfH°solid	-943.21 kJ/mol
Standard enthalpy of combustion ΔcH°solid	-1205.58 kJ/mol
Disclaimer and references

Oxaloacetic acid is an organic compound with the chemical formula HO₂CC(O)CH₂CO₂H. It also has other names (see Table) and its conjugate base is called "oxaloacetate." This four-carbon dicarboxylic acid is an protonated varient of oxaloacetate, which is an intermediate of the citric acid cycle and gluconeogenesis. Oxaloacetate forms upon oxidation of L-malate, catalysed by malate dehydrogenase, and reacts with Acetyl-CoA to form citrate, catalysed by citrate synthase. It also forms in the mesophyll of plants by the condensation of CO₂ with phosphoenolpyruvate, catalysed by oxaloacetate decarboxylase. It can be arise from pyruvate via an anaplerotic reaction. Image File history File links Oxaloacetic_acid. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... This article or section does not cite any references or sources. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ... For other uses, see Density (disambiguation). ... The acid dissociation constant (Ka), also known as the acidity constant or the acid-ionization constant, is a specific equilibrium constant for the reaction of an acid with its conjugate base in aqueous solution [1]. // When an acid dissolves in water, it partly dissociates forming hydronium ions and its conjugate... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The EINECS number (for European Inventory of Existing Chemical Substances) is a registry number given to each chemical substance commercially available in the European Union between 1 January 1971 and 18 September 1981. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... The standard enthalpy of formation or standard heat of formation of a compound is the change of enthalpy that accompanies the formation of 1 mole of a substance in its standard state from its constituent elements in their standard states (the most stable form of the element at 1 atmosphere... Standard enthalpy of Combustion is the Enthalpy change when one mole of a substance is totally combusted in oxygen, and is measured at 298K and 1 atmospheric pressure. ... Benzene is the simplest of the arenes, a family of organic compounds An organic compound is any member of a large class of chemical compounds whose molecules contain carbon and hydrogen; therefore, carbides, carbonates, carbon oxides and elementary carbon are not organic (see below for more on the definition controversy... In the field of chemistry, in the Brønsted-Lowry (protonic) theory of acids and bases, a conjugate base is the basic member, X-, of a pair of compounds that differ only by the presence or absence of a proton at a certain position. ... For other uses, see Carbon (disambiguation). ... Dicarboxylic acids are organic compounds that are substituted with two carboxylic acid functional groups. ... Overview of the citric acid cycle The citric acid cycle (also known as the tricarboxylic acid cycle, the TCA cycle, or the Krebs cycle, after Hans Adolf Krebs who identified the cycle) is a series of chemical reactions of central importance in all living cells that use oxygen as part... Pyruvic acid Oxaloacetic acid Phosphoenolpyruvate Fructose 1,6-bisphosphate Fructose 6-phosphate Glucose-6-phosphate Glucose Gluconeogenesis is the generation of glucose from non-sugar carbon substrates like pyruvate, lactate, glycerol, and amino acids (primarily alanine and glutamine). ... The most fundamental reactions in chemistry are the redox processes. ... Malic acid is a tart-tasting organic acid that plays a role in many sour or tart foods. ... Categories: Biochemistry stubs | EC 1. ... Categories: Biochemistry stubs | Thiols ... Chemical strucutre of citric acid. ... The enzyme citrate synthase (E.C. 2. ... This article is about the leaf, a plant organ. ... Carbon dioxide is a chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom. ... Name Phosphoenolpyruvate; Phosphoenolpyruvic acid; PEP Formula C3H5O6P Mass 167. ... Oxaloacetate decarboxylase is a carboxy-lyase involved in the conversion of oxaloacetate into pyruvate. ... Pyruvate (CH3COCOO−) is the ionized form of pyruvic acid. ... - of Greek origin, meaning to fill up Anaplerotic reactions are those that form intermediates of the TCA or citric acid cycle. ...

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 pK_a value of 13.02. The enzyme fumarase A from E. coli catalyses the conversion between the keto and enol forms. Enol (or, more officially, but less commonly: alkenol) is an alkene with hydroxyl group on one of the carbon atoms of the double bond. ... The acid dissociation constant (Ka), also known as the acidity constant or the acid-ionization constant, is a specific equilibrium constant for the reaction of an acid with its conjugate base in aqueous solution [1]. // When an acid dissolves in water, it partly dissociates forming hydronium ions and its conjugate... Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ... Fumarase is an enzyme involved in the Krebs Cycle that catalyzes the hydration (addition of H2O across a double bond) of Fumarate to L-malate (the natural optical isomer of a protein as apposed to the d isomer) Fumarase Deficiency In humans, Fumarase Deficiency is an enzyme irregularity that causes... E. coli redirects here. ...

Oxaloacetic acid is unstable in solution, decomposing to pyruvic acid by decarboxylation over a period of hours (room temperature) or days (0 °C). Refrigerated storage of the solid is therefore recommended. Pyruvic acid (CH3COCO2H) is an alpha-keto acid which plays an important role in biochemical processes. ... A Decarboxylation is any chemical reaction in which a carboxyl group (-COOH) is split off from a compound as carbon dioxide (CO2). ...

Relationship of oxaloacetic acid, malic acid, and aspartic acid

Image File history File links Size of this preview: 378 × 600 pixelsFull resolution (626 × 993 pixel, file size: 22 KB, MIME type: image/png) File historyClick on a date/time to view the file as it appeared at that time. ... Image File history File links Size of this preview: 378 × 600 pixelsFull resolution (626 × 993 pixel, file size: 22 KB, MIME type: image/png) File historyClick on a date/time to view the file as it appeared at that time. ...

See also