Dioxosuccinic acid

Dioxosuccinic acid
Names
	Preferred IUPAC name Dioxobutanedioic acid
	Other names Dioxosuccinic acid; 2,3-Dioxosuccinic acid
Identifiers
CAS Number	7580-59-8 [ChemSpider];
3D model (JSmol)	Interactive image;
Beilstein Reference	956740
ChEBI	CHEBI:30799;
ChemSpider	74061 ;
ECHA InfoCard	100.028.622
EC Number	231-483-8;
PubChem CID	82062;
UNII	D82LW8DKT2 ;
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) 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−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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.^[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

References

^ Ján Farkaš, Beatrix Farkaš (1988), Technology and Biochemistry of Wine. CRC Press, 744 pages. ISBN 2-88124-070-4.
^ Victorian College of Pharmacy, Dept. of Chemistry (1959), Notes on qualitative analysis.

[farkas-1] Ján Farkaš, Beatrix Farkaš (1988), Technology and Biochemistry of Wine. CRC Press, 744 pages. ISBN 2-88124-070-4.

[vic-2] Victorian College of Pharmacy, Dept. of Chemistry (1959), Notes on qualitative analysis.

[1]

[2]

Dioxosuccinic acid

Contents

Occurrence

Reactions

See also

References

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