Dioxosuccinic acid

Dioxosuccinic acid
Identifiers
CAS number 7580-59-8
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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, C4O62− or (O-(C=O)4-O)2−. 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, C4HO6 − or (HO-(C=O)4-O)−.

Contents

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, 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.[2]:p.187

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.