Mesaconic acid

Mesaconic acid
Names
	Preferred IUPAC name (2E)-2-Methylbut-2-enedioic acid
Identifiers
CAS Number	498-24-8 ;
3D model (JSmol)	Interactive image;
3DMet	B00338;
ChEBI	CHEBI:16600 ;
ChemSpider	10289044 ;
ECHA InfoCard	100.007.146
EC Number	207-859-2;
KEGG	C01732 ;
PubChem CID	638129;
UNII	90UTM639KK;
CompTox Dashboard (EPA)	DTXSID10883407 ;
	InChI InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+ Key: HNEGQIOMVPPMNR-NSCUHMNNSA-N ; InChI=1/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+ Key: HNEGQIOMVPPMNR-NSCUHMNNBN;
	SMILES OC(/C(C)=C/C(O)=O)=O;
Properties
Chemical formula	C5H6O4
Molar mass	130.10 g/mol
Density	1.31 g/cm3
Melting point	204 to 205 °C (399 to 401 °F; 477 to 478 K)
Boiling point	250 °C (482 °F; 523 K) (decomposes)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
	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

Mesaconic acid is one of several isomeric carboxylic acids obtained from citric acid. It is a colorless solid.

Synthesis and reactions

It is prepared from citric acid, which is first converted to itaconic anhydride by dehydration and decarboxylation. Itaconic acid anhydride is isomerized to citraconic anhydride, which is hydrolyzed and the resulting acid further isomerized under acid-catalysis to give mesaconic acid.^[1]

Hydration of mesaconic acid, a conversion catalyzed by mesaconyl-C4-CoA hydratase, gives citramalic acid.^[2]

History

This acid was studied for the first time by Jacobus H. van 't Hoff in 1874.^[3] It was later shown to be produced by Clostridium tetanomorphum. Further studies showed that this organic compound is involved in the biosynthesis of vitamin B12. It is a competitive inhibitor of fumarate reduction.^[4]^[5]

The compound has been considered as a renewable precursor to the commodity chemical methacrylic acid.^[6]

References

^ R. L. Shriner; S. G. Ford; L. J. Roll (1931). "Mesaconic Acid". Org. Synth. 11: 74. doi:10.15227/orgsyn.011.0074.
^ Berg, Ivan A. (2011). "Ecological Aspects of the Distribution of Different Autotrophic CO 2 Fixation Pathways". Applied and Environmental Microbiology. 77 (6): 1925–1936. Bibcode:2011ApEnM..77.1925B. doi:10.1128/AEM.02473-10. PMC 3067309. PMID 21216907.
^ "Mesaconic acid". Archived from the original on November 17, 2005. Retrieved September 8, 2005.
^ "Barker, Horace Albert". The Stadtman Way: The Story of Two Biochemists at NIH. Office of NIH History. Retrieved December 21, 2011.
^ Switzer, Robert L.; Stadtman, Earl R.; Stadtman, Thressa C. (2004). "H.A. Barker". Biographical Memoirs. 84. National Academies Press: 3–22. PMID 15484416. Retrieved December 21, 2011.
^ Santosh K. Yadav; Kevin M. Schmalbach; Emre Kinaci; Joseph F. Stanzione III; Giuseppe R. Palmese (2018). "Recent advances in plant-based vinyl ester resins and reactive diluents". European Polymer Journal. 98: 199–215. doi:10.1016/j.eurpolymj.2017.11.002.

[1] R. L. Shriner; S. G. Ford; L. J. Roll (1931). "Mesaconic Acid". Org. Synth. 11: 74. doi:10.15227/orgsyn.011.0074.

[2] Berg, Ivan A. (2011). "Ecological Aspects of the Distribution of Different Autotrophic CO 2 Fixation Pathways". Applied and Environmental Microbiology. 77 (6): 1925–1936. Bibcode:2011ApEnM..77.1925B. doi:10.1128/AEM.02473-10. PMC 3067309. PMID 21216907.

[3] "Mesaconic acid". Archived from the original on November 17, 2005. Retrieved September 8, 2005.

[4] "Barker, Horace Albert". The Stadtman Way: The Story of Two Biochemists at NIH. Office of NIH History. Retrieved December 21, 2011.

[5] Switzer, Robert L.; Stadtman, Earl R.; Stadtman, Thressa C. (2004). "H.A. Barker". Biographical Memoirs. 84. National Academies Press: 3–22. PMID 15484416. Retrieved December 21, 2011.

[6] Santosh K. Yadav; Kevin M. Schmalbach; Emre Kinaci; Joseph F. Stanzione III; Giuseppe R. Palmese (2018). "Recent advances in plant-based vinyl ester resins and reactive diluents". European Polymer Journal. 98: 199–215. doi:10.1016/j.eurpolymj.2017.11.002.

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