Dioxosuccinic acid

Dioxosuccinic acid

Names
Preferred IUPAC name Dioxobutanedioic acid
Other names Dioxosuccinic acid 2,3-Dioxosuccinic acid
Identifiers
CAS Number	7580-59-8 Y[ChemSpider]
3D model (JSmol)	Interactive image
Beilstein Reference	956740
ChEBI	CHEBI:30799
ChemSpider	74061 Y
ECHA InfoCard	100.028.622
EC Number	231-483-8
PubChem CID	82062
UNII	D82LW8DKT2 Y
CompTox Dashboard (EPA)	DTXSID30226716
InChI 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
SMILES C(=O)(C(=O)C(=O)O)C(=O)O
Properties
Chemical formula	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). N verify (what is YN ?) 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, 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.

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

• Mesoxalic acid
• Oxaloacetic acid (or oxosuccinic acid)
• Fumaric acid