Dioxosuccinic acid

Dioxosuccinic acid or dioxobutanedioic acid is an organic compound with formula C4H2O6 or HO−(C=O)4−OH.

Dioxosuccinic acid
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Dioxobutanedioic acid
Other names
Dioxosuccinic acid
2,3-Dioxosuccinic acid
Identifiers
3D model (JSmol)
956740
ChEBI
ChemSpider
ECHA InfoCard 100.028.622
EC Number
  • 231-483-8
UNII
  • InChI=1S/C4H2O6/c5-1(3(7)8)2(6)4(9)10/h(H,7,8)(H,9,10) ☒N
    Key: BLNNXYDKWOJQGK-UHFFFAOYSA-N ☒N
  • InChI=1/C4H2O6/c5-1(3(7)8)2(6)4(9)10/h(H,7,8)(H,9,10)
    Key: BLNNXYDKWOJQGK-UHFFFAOYAK
  • C(=O)(C(=O)C(=O)O)C(=O)O
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).
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Infobox references

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.

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

References
  1. Ján Farkaš, Beatrix Farkaš (1988), Technology and Biochemistry of Wine. CRC Press, 744 pages. ISBN 2-88124-070-4.
  2. Victorian College of Pharmacy, Dept. of Chemistry (1959), Notes on qualitative analysis.
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