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
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

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.^{[citation needed]}

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

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