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Dioxosuccinic acid

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Dioxosuccinic acid
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name Dioxobutanedioic acid
Other names Dioxosuccinic acid
2,3-Dioxosuccinic acid
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 956740
ChEBI
ChemSpider
ECHA InfoCard 100.028.622 Edit this at Wikidata
EC Number
  • 231-483-8
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H2O6/c5-1(3(7)8)2(6)4(9)10/h(H,7,8)(H,9,10)Key: BLNNXYDKWOJQGK-UHFFFAOYSA-N
  • InChI=1/C4H2O6/c5-1(3(7)8)2(6)4(9)10/h(H,7,8)(H,9,10)Key: BLNNXYDKWOJQGK-UHFFFAOYAK
SMILES
  • C(=O)(C(=O)C(=O)O)C(=O)O
Properties
Chemical formula C4H2O6
Molar mass 146.054 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N 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, C
4O
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 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.

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.

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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