| Revision as of 21:30, 12 May 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit |
Latest revision as of 19:34, 18 August 2022 edit undoFswitzer4 (talk | contribs)Extended confirmed users10,572 editsm Added UNII |
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{{Chembox |
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{{Chembox |
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| verifiedrevid = 407275781 |
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| verifiedrevid = 428824923 |
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| ImageFile1 = Dioxosuccinic acid.svg |
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| ImageFile1 = Dioxosuccinic acid.svg |
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| ImageSize1 = 180px |
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| ImageName1 = Skeletal formula |
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| ImageName1 = Skeletal formula |
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| ImageFile2 = Dioxosuccinic-acid-3D-balls.png |
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| ImageFile2 = Dioxosuccinic-acid-3D-balls.png |
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| ImageName2 = Ball-and-stick model |
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| ImageName2 = Ball-and-stick model |
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| PIN = Dioxobutanedioic acid |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = Dioxosuccinic acid<br/>2,3-Dioxosuccinic acid |
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| CASNo = 7580-59-8 |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|ChemSpider}} |
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| CASNo = 7580-59-8 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = D82LW8DKT2 |
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| Beilstein = 956740 |
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| ChEBI = 30799 |
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| EINECS = 231-483-8 |
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| PubChem = 82062 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 74061 |
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| SMILES = C(=O)(C(=O)C(=O)O)C(=O)O |
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| InChI = 1/C4H2O6/c5-1(3(7)8)2(6)4(9)10/h(H,7,8)(H,9,10) |
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| InChIKey = BLNNXYDKWOJQGK-UHFFFAOYAK |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C4H2O6/c5-1(3(7)8)2(6)4(9)10/h(H,7,8)(H,9,10) |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = BLNNXYDKWOJQGK-UHFFFAOYSA-N |
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}} |
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|Section2={{Chembox Properties |
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| C=4 | H=2 | O=6 |
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|Section3={{Chembox Hazards |
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'''Dioxosuccinic acid''' or '''dioxobutanedioic acid''' is an ] with formula C<sub>4</sub>H<sub>2</sub>O<sub>6</sub> or HO-(C=O)<sub>4</sub>-OH. |
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'''Dioxosuccinic acid''' or '''dioxobutanedioic acid''' is an ] with formula C<sub>4</sub>H<sub>2</sub>O<sub>6</sub> or HO−(C=O)<sub>4</sub>−OH. |
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Removal of two ]s from the molecule would yield the '''dioxosuccinate''' ], C<sub>4</sub>O<sub>6</sub><sup>2−</sup> or (O-(C=O)<sub>4</sub>-O)<sup>2−</sup>. This is one of the ]s, which consist solely of carbon and oxygen. The name is also used for salts containing that anion, and for ] with the ]. |
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Removal of two ]s from the molecule would yield the '''dioxosuccinate''' ], {{chem|C|4|O|6|2−}} or <sup>−</sup>O−(C=O)<sub>4</sub>−O<sup>−</sup>. This is one of the ]s, which consist solely of carbon and oxygen. The name is also used for salts containing that anion, and for ] with the ]. |
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Removal of a single proton would result in the monovalent anion '''hydrogendioxosuccinate''', C<sub>4</sub>HO<sub>6</sub> <sup>−</sup> or (HO-(C=O)<sub>4</sub>-O)<sup>−</sup>. |
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Removal of a single proton would result in the monovalent anion '''hydrogendioxosuccinate''', {{chem|C|4|HO|6|−}} or HO−(C=O)<sub>4</sub>−O<sup>−</sup>. |
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==Occurrence== |
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==Occurrence== |
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Dioxosuccinic acid is one of the ], from the ] of ] via ].<ref name="farkas"> |
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Dioxosuccinic acid is one of the ], from the ] of ] via ].<ref name="farkas">Ján Farkaš, Beatrix Farkaš (1988), ''Technology and Biochemistry of Wine''. CRC Press, 744 pages. {{ISBN|2-88124-070-4}}.</ref> |
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By Ján Farkaš, Beatrix Farkas (1988), ''Technology and Biochemistry of Wine''.CRC Press, 744 pages. ISBN 2881240704. |
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</ref> |
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==Reactions== |
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==Reactions== |
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The acid combines with two molecules of water to produce ], C<sub>4</sub>H<sub>6</sub>O<sub>8</sub> or HO-(C=O)-(C(OH)<sub>2</sub>)<sub>2</sub>-(C=O)-OH. Indeed the product traded under the name "dioxosuccinic acid hydrate" appears to be that substance. |
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The acid combines with two molecules of water to produce dihydroxytartaric acid, the ketone hydrate form, C<sub>4</sub>H<sub>6</sub>O<sub>8</sub> or HO−(C=O)−(C(OH)<sub>2</sub>)<sub>2</sub>−(C=O)−OH. Indeed, the product traded under the name "dioxosuccinic acid hydrate" appears to be that substance.{{cn|date=May 2019}} |
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On the other hand, dihydroxytartaric acid behaves like dioxosuccinic acid in some reactions; for example, it reacts with ] in the presence of ] to yield the ester ].<ref name="vic"> |
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Dihydroxytartaric acid behaves like dioxosuccinic acid in some reactions; for example, it reacts with ] in the presence of ] to yield the ester ], upon isolation.<ref name="vic">Victorian College of Pharmacy, Dept. of Chemistry (1959), .</ref>{{rp|p.187}} |
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Victorian College of Pharmacy., Dept. of Chemistry (1959), . |
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</ref>{{rp|p.187}} |
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==See also== |
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==See also== |
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{{Reflist}} |
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{{Reflist}} |
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