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Dioxosuccinic acid

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Dioxosuccinic acid
Skeletal formula
Ball-and-stick model
Identifiers
CAS Number
ECHA InfoCard 100.028.622 Edit this at Wikidata
CompTox Dashboard (EPA)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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, C4O6 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 moiety.

Removal of a single proton would result in the monovalent anion hydrogendioxosuccinate, C4HO6 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.

Reactions

The acid combines with two molecules of water to produce dihydroxytartaric acid, 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.

On the other hand, 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.

See also

References

  1. By Ján Farkaš, Beatrix Farkas (1988), Technology and Biochemistry of Wine.CRC Press, 744 pages. ISBN 2881240704.
  2. Victorian College of Pharmacy., Dept. of Chemistry (1959), Notes on qualitative analysis.
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