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Revision as of 17:37, 8 July 2011 editEdgar181 (talk | contribs)Extended confirmed users196,325 edits citraconic acid← Previous edit		Latest revision as of 17:33, 25 September 2023 edit undoTrappist the monk (talk | contribs)Administrators480,242 editsm cite repair;Tag: AWB
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	{{chembox		{{Chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 388451898
			| Watchedfields = changed
		⚫	| verifiedrevid = 438444350
	| ImageFile = Mesaconic-acid-2D-skeletal.svg		| ImageFile = Mesaconic-acid-2D-skeletal.svg
	| ImageSize = 180px		| ImageSize = 180px
Line 6:		Line 8:
	| ImageFile1 = Mesaconic-acid-3D-balls.png		| ImageFile1 = Mesaconic-acid-3D-balls.png
	| ImageName1 = Ball-and-stick model		| ImageName1 = Ball-and-stick model
	| IUPACName = (2''E'')-2-Methyl-2-butenedioic acid		| PIN = (2''E'')-2-Methylbut-2-enedioic acid
	| OtherNames =		| OtherNames =
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
			| CASNo_Ref = {{cascite|correct|??}}
	| CASNo = 498-24-8
	| PubChem =		| CASNo = 498-24-8
	| SMILES = OC(/C(C)=C/C(O)=O)=O		| PubChem = 638129
			| SMILES = OC(/C(C)=C/C(O)=O)=O
			| EINECS = 207-859-2
⚫	}}
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
⚫	| Section2 = {{Chembox Properties
			| ChemSpiderID = 10289044
⚫	| Formula = C<sub>5</sub>H<sub>6</sub>O<sub>4</sub>
			| InChI = 1/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+
⚫	| MolarMass = 130.10 g/mol
			| InChIKey = HNEGQIOMVPPMNR-NSCUHMNNBN
⚫	| Appearance =
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
⚫	| Density = 1.31 g/cm<sup>3</sup>
			| StdInChI = 1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+
	| MeltingPt = 204-205 °C
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
	| BoilingPt = 250 °C (decomp.)
			| StdInChIKey = HNEGQIOMVPPMNR-NSCUHMNNSA-N
⚫	| Solubility =
			| RTECS =
⚫	}}
			| MeSHName =
⚫	| Section3 = {{Chembox Hazards
			| ChEBI_Ref = {{ebicite|changed|EBI}}
⚫	| MainHazards =
	| FlashPt =		| ChEBI = 16600
			| 3DMet = B00338
	| Autoignition =
			| UNII = 90UTM639KK
⚫	}}
			| KEGG_Ref = {{keggcite|correct|kegg}}
			| KEGG = C01732
		⚫	}}
		⚫	|Section2={{Chembox Properties
		⚫	| Formula = C<sub>5</sub>H<sub>6</sub>O<sub>4</sub>
		⚫	| MolarMass = 130.10 g/mol
		⚫	| Appearance =
		⚫	| Density = 1.31 g/cm<sup>3</sup>
			| MeltingPtC = 204 to 205
			| MeltingPt_notes =
			| BoilingPtC = 250
			| BoilingPt_notes = (decomposes)
		⚫	| Solubility =
		⚫	}}
		⚫	|Section3={{Chembox Hazards
		⚫	| MainHazards =
			| FlashPt =
			| AutoignitionPt =
			| GHSPictograms = {{GHS07}}
			| GHSSignalWord = Warning
			| HPhrases = {{H-phrases|315|319|335}}
			| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
		⚫	}}
	}}		}}
	'''Mesaconic acid''' is one of several ]ic ]s obtained from ]. It is the ''cis''-isomer of ]. It is used as a ].		'''Mesaconic acid''' is one of several ]ic ]s obtained from ]. It is a colorless solid.
			==Synthesis and reactions==
⚫	==History==
			It is prepared from ], which is first converted to ] by dehydration and decarboxylation. Itaconic acid anhydride is isomerized to ], which is hydrolyzed and the resulting acid further isomerized under acid-catalysis to give mesaconic acid.<ref>{{cite journal|title=Mesaconic Acid|author=] |author2=S. G. Ford |author3=L. J. Roll
	This acid was studied for the first time by ] ] ] in 1874. Later ] ] ] and his team successfully isolated this acid from fermenting bacterium ] in 1950s. Further studies led him to discover this organic compound was involved in ] ]s synthesis.
			|journal=Org. Synth.|year=1931|volume=11|page=74|doi=10.15227/orgsyn.011.0074}}</ref>
			Hydration of mesaconic acid, a conversion catalyzed by mesaconyl-C4-CoA hydratase, gives ].<ref>{{cite journal |doi=10.1128/AEM.02473-10|title=Ecological Aspects of the Distribution of Different Autotrophic CO 2 Fixation Pathways|year=2011|last1=Berg|first1=Ivan A.|journal=Applied and Environmental Microbiology|volume=77|issue=6|pages=1925–1936|pmid=21216907|pmc=3067309|bibcode=2011ApEnM..77.1925B}}</ref>
	Recent studies revealed this acid is a ] of ] ].
		⚫	==History==
			This acid was studied for the first time by ] in 1874.<ref>{{cite web|title=Mesaconic acid |url=http://dbhs.wvusd.k12.ca.us/webdocs/Chem-History/Van't-Hoff-1874.html |access-date=September 8, 2005 |archive-url=https://web.archive.org/web/20051117102410/http://dbhs.wvusd.k12.ca.us/webdocs/Chem-History/Van%27t-Hoff-1874.html |archive-date=November 17, 2005 }}</ref> It was later shown to be produced by ''Clostridium tetanomorphum''. Further studies showed that this organic compound is involved in the biosynthesis of ]. It is a ] of ] ].<ref>{{cite web|title=Barker, Horace Albert|work=The Stadtman Way: The Story of Two Biochemists at NIH|publisher=Office of NIH History|url=http://www.history.nih.gov/exhibits/stadtman/bios.htm#Barker
			| access-date = December 21, 2011}}</ref><ref>{{cite journal |last1= Switzer|first1= Robert L.|last2= Stadtman|first2= Earl R.|last3= Stadtman|first3= Thressa C.|year= 2004|title= H.A. Barker|journal= Biographical Memoirs|volume= 84|pages= 3–22|publisher= National Academies Press|pmid= 15484416|url= http://lab.nap.edu/openbook.php?record_id=10992&page=3|access-date= December 21, 2011}}</ref>
			The compound has been considered as a renewable precursor to the commodity chemical ].<ref>{{cite journal|title=Recent advances in plant-based vinyl ester resins and reactive diluents|author=Santosh K. Yadav |author2=Kevin M. Schmalbach |author3=Emre Kinaci |author4=Joseph F. Stanzione III |author5=Giuseppe R. Palmese |journal=European Polymer Journal|year=2018|volume=98 |page=199–215|doi=10.1016/j.eurpolymj.2017.11.002|doi-access=free}}</ref>
	==References==		==References==
			<references />
	{{refstyle}}
	*{{cite web|title=Mesaconic acid|work=Mesaconic acid|url=http://dbhs.wvusd.k12.ca.us/webdocs/Chem-History/Van't-Hoff-1874.html|accessdate=September 8, 2005 |archiveurl = http://web.archive.org/web/20051117102410/http://dbhs.wvusd.k12.ca.us/webdocs/Chem-History/Van't-Hoff-1874.html <!-- Bot retrieved archive --> |archivedate = November 17, 2005}}
	*{{cite web|title=The Stadtman Way|work=Horace Albert Barker|url=http://www.history.nih.gov/exhibits/stadtman/bios.htm#Barker
	|accessdate=September 8, 2005}}
	*{{cite web|title=The National Academies Press|work=Biographical Memoirs V.84 (2004)|url=http://lab.nap.edu/openbook/0309089573/html/14.html|accessdate=September 8, 2005}}
	*''Merck Index'', 11th Edition, '''5806'''.
	]		]
	]
	]