Chemistry: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 | |
3D model (JSmol)
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| 956740 | |
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PubChem CID
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| Properties | |
| 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). | |
 verify (what is   ?)
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| 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, C4O2−6 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, C4HO−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
References
- ↑ Ján Farkaš, Beatrix Farkaš (1988), Technology and Biochemistry of Wine. CRC Press, 744 pages. ISBN:2-88124-070-4.
- ↑ Victorian College of Pharmacy, Dept. of Chemistry (1959), Notes on qualitative analysis.
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