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{{Chembox |
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{{Chembox |
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| verifiedrevid = 443676222 |
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| verifiedrevid = 444767222 |
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| ImageFile = Citraconic acid.svg |
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| ImageFile = Citraconic acid.svg |
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| PIN = (2''Z'')-2-Methylbut-2-enedioic acid |
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| ImageSize = 200px |
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| OtherNames = 2-Methylmaleic acid<br />Citraconate<br />Methylmaleic acid<br />''cis''-Methylbutenedioic acid |
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| IUPACName = (2''Z'')-2-Methylbut-2-enedioic acid |
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|Section1={{Chembox Identifiers |
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| OtherNames = Citraconate; Methylmaleic acid; ''cis''-Methylbutenedioic acid |
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| CASNo = 498-23-7 |
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| Section1 = {{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 498-23-7 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 643798 |
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| UNII = 0RQ6CXO9KD |
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| PubChem = 643798 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 553689 |
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| ChemSpiderID = 553689 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 17626 |
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| ChEBI = 17626 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB04734 |
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| DrugBank = DB04734 |
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| EINECS = 207-858-7 |
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| KEGG = C02226 |
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| 3DMet = B00408 |
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| SMILES = O=C(O)\C=C(/C(=O)O)C |
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| SMILES = O=C(O)\C=C(/C(=O)O)C |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2- |
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| StdInChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2- |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = HNEGQIOMVPPMNR-IHWYPQMZSA-N |
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| StdInChIKey = HNEGQIOMVPPMNR-IHWYPQMZSA-N |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=5|H=6|O=4 |
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| C=5 | H=6 | O=4 |
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| Appearance = Monoclinic crystals<ref name=Merck>{{Merck12th}}</ref> |
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| Appearance = Monoclinic crystals<ref name=Merck>{{Merck12th}}</ref> |
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| Density = 1.62 g/cm<small>3</small><ref name=Merck/> |
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| Density = 1.62 g/cm<small>3</small><ref name=Merck/> |
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| MeltingPt = ~90 °C (decomposition)<ref name=Merck/> |
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| MeltingPt = ~90 °C (decomposition)<ref name=Merck/> |
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| BoilingPt = |
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| BoilingPt = |
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| Solubility = Freely soluble<ref name=Merck/> |
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| Solubility = Freely soluble<ref name=Merck/> |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| MainHazards = |
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| FlashPt = |
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| FlashPt = |
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| Autoignition = |
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| AutoignitionPt = |
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| GHSPictograms = {{GHS07}} |
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| RPhrases = {{R22}}<ref name=Aldrich></ref> |
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| GHSSignalWord = Warning |
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| SPhrases = {{S36}}<ref name=Aldrich/> |
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| HPhrases = {{H-phrases|302}} |
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| PPhrases = {{P-phrases|264|270|301+312|330|501}} |
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'''Citraconic acid''' is an ] with the formula CH<sub>3</sub>C<sub>2</sub>H(CO<sub>2</sub>H)<sub>2</sub>. It is a white solid. The alkene is ]. The related trans alkene is called ]. It is one of the ]s formed upon the heating of ].<ref name=Merck/> Citraconic acid can be produced, albeit inefficiently, by oxidation of xylene and methylbutanols. The acid displays the unusual property of spontaneously forming the anhydride, which, unlike ], is a liquid at room temperature.<ref name = ullmann>{{Ullmann | title = Maleic and Fumaric Acids | author1 = Kurt Lohbeck | author2 = Herbert Haferkorn | author3 = Werner Fuhrmann | author4 = Norbert Fedtke | doi = 10.1002/14356007.a16_053 }}</ref> |
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'''Citraconic acid''' is one of the ]s formed upon the heating of ].<ref name=Merck/> It is the ''trans''-] of ]. |
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] |
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In the laboratory, citraconic acid can be produced by thermal isomerization of ] to give '''citraconic anhydride''', which can be hydrolyzed to citraconic acid.<ref>{{cite journal|author1=R. L. Shriner|author2=S. G. Ford|author3= l. J. Roll|journal=Org. Synth.|year=1931|volume=28|page=28|doi=10.15227/orgsyn.011.0028|title=Citraconic Anhydride and Citraconic Acid}}</ref> The required itaconic acid anhydride is obtained by dry distillation of ]. |
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==References== |
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==References== |
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{{alkene-stub}} |
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{{organic-compound-stub}} |
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