Dioxosuccinic acid
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Names | |
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Preferred IUPAC name Dioxobutanedioic acid | |
Other names Dioxosuccinic acid 2,3-Dioxosuccinic acid | |
Identifiers | |
CAS Number |
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3D model (JSmol) |
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Beilstein Reference | 956740 |
ChEBI |
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ChemSpider |
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ECHA InfoCard | 100.028.622 ![]() |
EC Number |
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PubChem CID |
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UNII |
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CompTox Dashboard (EPA) |
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InChI
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Properties | |
Chemical formula | C4H2O6 |
Molar mass | 146.054 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ![]() ![]() ![]() Infobox references |
Dioxosuccinic acid or dioxobutanedioic acid is an organic compound with formula C4H2O6 or HO−(C=O)4−OH.
Removal of two protons from the molecule would yield the dioxosuccinate anion, C
4O2−
6 or −O−(C=O)4−O−. This is one of the oxocarbon anions, which consist solely of carbon and oxygen. The name is also used for salts containing that anion, and for esters with the [−O−(C=O)4−O−] moiety.
Removal of a single proton would result in the monovalent anion hydrogendioxosuccinate, C
4HO−
6 or HO−(C=O)4−O−.
Occurrence
Dioxosuccinic acid is one of the acids occurring naturally in wine, from the oxidation of tartaric acid via dihydroxyfumaric acid.[1]
Reactions
The acid combines with two molecules of water to produce dihydroxytartaric acid, the ketone hydrate form, C4H6O8 or HO−(C=O)−(C(OH)2)2−(C=O)−OH. Indeed, the product traded under the name "dioxosuccinic acid hydrate" appears to be that substance.[citation needed]
Dihydroxytartaric acid behaves like dioxosuccinic acid in some reactions; for example, it reacts with ethanol in the presence of hydrogen chloride to yield the ester diethyl dioxosuccinate, upon isolation.[2]: p.187
See also
- Mesoxalic acid
- Oxaloacetic acid (or oxosuccinic acid)
- Fumaric acid