Oxaloacetic acid

Oxaloacetic acid
IUPAC name Oxobutanedioic acid
Other names Oxaloacetic acid Oxalacetic acid Oxosuccinic acid
Identifiers
CAS number	328-42-7 Y
PubChem	970
ChemSpider	945 Y
EC number	206-329-8
ChEBI	CHEBI:30744 Y
Jmol-3D images	Image 1
SMILES O=C(O)C(=O)CC(=O)O
InChI InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9) Y Key: KHPXUQMNIQBQEV-UHFFFAOYSA-N Y
Properties
Molecular formula	C4H4O5
Molar mass	132.07 g/mol
Density	? g/cm3
Melting point	161 °C
Thermochemistry
Std enthalpy of formation ΔfHo298	-943.21 kJ/mol
Std enthalpy of combustion ΔcHo298	-1205.58 kJ/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Oxaloacetic acid (also oxalacetic acid) is an organic compound with the chemical formula C₄H₄O₅ or HOOC-(C=O)-(CH₂)-COOH. It also has other names (see the table).

Its fully deprotonated derivative is the oxaloacetate anion, C₄H₂O₅²⁻ or [(C=O)₂(CH₂)(C=O)]²⁻; this name is also used for esters that contain the divalent [-O(C=O)₂(CH₂)(C=O)O-] moiety. Loss of a single proton gives the acid's conjugate base, the anion hydrogenoxaloacetate anion H(C=O)₂(CH₂)(C=O)⁻.

Function

This four-carbon dicarboxylic acid is a protonated variant of oxaloacetate, which is an intermediate of the citric acid cycle^[1] 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 PEP Carboxykinase. It can arise from pyruvate via an anaplerotic reaction. Oxaloacetate is also a potent inhibitor of Complex II.

Relationship of oxaloacetic acid, malic acid, and aspartic acid

Chemical properties

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).^{[clarification needed]} The enol proton has a pK_a value of 13.02.

Oxaloacetate is unstable in solution, decomposing to pyruvate by decarboxylation over a period of hours (room temperature) or days (0 °C).^{[citation needed]} Refrigerated storage of the solid is therefore recommended.

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles.^[2]

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Citric_acid_cycle edit

See also

• dioxosuccinic acid

References

1. ^ "Citric Acid Cycle Reactions". http://www.elmhurst.edu/~chm/vchembook/611citricrx.html. Retrieved 2009-04-18. 
2. ^ The interactive pathway map can be edited at WikiPathways: "TCACycle_WP78". http://www.wikipathways.org/index.php/Pathway:WP78. 

This article about metabolism is a stub. You can help Wikipedia by expanding it.v · Categories: Citric acid cycle Citric acid cycle compounds Dicarboxylic acids Keto acids Biochemistry stubs Wikimedia Foundation. 2010. Игры ⚽ Поможем сделать НИР Simon Mayo Fedja Jelecak Look at other dictionaries: oxaloacetic acid — A ketodicarboxylic acid and important intermediate in the tricarboxylic acid cycle; the product formed when l aspartic acid acts as an amine donor in transamination reactions. SYN: ketosuccinic acid, oxosuccinic acid. * * * …   Medical dictionary oxaloacetic acid — noun an acid formed by oxidation of maleic acid (as in metabolism of fats and carbohydrates) • Syn: ↑oxalacetic acid • Hypernyms: ↑acid * * * noun see oxalacetic acid * * * /ok seuh loh euh see tik, ok , ok sal oh , sal /, Biochem. a crystalline… …   Useful english dictionary oxaloacetic acid — also oxalacetic acid noun Etymology: oxalic + acetic acid Date: 1896 a crystalline acid C4H4O5 that is formed by reversible oxidation of malic acid (as in carbohydrate metabolism via the Krebs cycle) and in reversible transamination reactions (as …   New Collegiate Dictionary oxaloacetic acid — /ok seuh loh euh see tik, ok , ok sal oh , sal /, Biochem. a crystalline organic acid, C4H4O5, that is an important intermediate in the Krebs cycle, where it is formed by the oxidation of malic acid and is acetylated to form citric acid: also a… …   Universalium oxaloacetic acid — noun a) on of the constituents of the citric acid cycle, formed by the oxidation of malic acid and via the transamination of aspartic acid; an intermediate in the synthesis of amino acids and the metabolism of …   Wiktionary oxaloacetic acid — ox′a•lo•a•ce′tic ac′id [[t]ˈɒk sə loʊ əˈsi tɪk, ˌɒk , ɒkˈsæl oʊ , ˌsæl [/t]] n. biochem. a crystalline organic acid, C4H4O5, an important intermediate in the Krebs cycle, where it is formed by the oxidation of malic acid and is acetylated to form …   From formal English to slang oxaloacetic acid — /ɒksəloʊəˌsɛtɪk ˈæsəd/ (say oksuhlohuh.setik asuhd) noun a dibasic carboxylic acid, HOOCCH2CO.COOH, a key intermediary metabolite involved in the citric acid cycle and the formation of aspartic acid …   oxalacetic acid — noun an acid formed by oxidation of maleic acid (as in metabolism of fats and carbohydrates) • Syn: ↑oxaloacetic acid • Hypernyms: ↑acid * * * “+... noun or oxaloacetic acid “+ …   Useful english dictionary ox|al|a|cet|ic acid — «OK suh luh SEE tihk, SEHT ihk», = oxaloacetic acid. (Cf. ↑oxaloacetic acid) …   Useful english dictionary Dioxosuccinic acid — Identifiers CAS number …   Wikipedia 18+ © Academic, 2000-2024 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”