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Chemical compound From Wikipedia, the free encyclopedia
Citraconic acid is an organic compound with the formula CH3C2H(CO2H)2. It is a white solid. The alkene is cis. The related trans alkene is called mesaconic acid. It is one of the pyrocitric acids formed upon the heating of citric acid.[1] Citraconic acid can be produced, albeit inefficiently, by oxidation of xylene and methylbutanols. The acid displays the unusual property of spontaneously forming the anhydride, which, unlike maleic anhydride, is a liquid at room temperature.[2]
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Names | |
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Preferred IUPAC name
(2Z)-2-Methylbut-2-enedioic acid | |
Other names
2-Methylmaleic acid Citraconate Methylmaleic acid cis-Methylbutenedioic acid | |
Identifiers | |
3D model (JSmol) |
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3DMet | |
ChEBI | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.007.145 |
EC Number |
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KEGG | |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C5H6O4 | |
Molar mass | 130.099 g·mol−1 |
Appearance | Monoclinic crystals[1] |
Density | 1.62 g/cm3[1] |
Melting point | ~90 °C (decomposition)[1] |
Freely soluble[1] | |
Hazards | |
GHS labelling: | |
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Warning | |
H302 | |
P264, P270, P301+P312, P330, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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In the laboratory, citraconic acid can be produced by thermal isomerization of itaconic acid anhydride to give citraconic anhydride, which can be hydrolyzed to citraconic acid.[3] The required itaconic acid anhydride is obtained by dry distillation of citric acid.