Mesaconic acid

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

Mesaconic acid
Names
IUPAC name
(2E)-2-Methyl-2-butenedioic acid
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChemSpider
ECHA InfoCard 100.007.146
EC Number
  • 207-859-2
KEGG
UNII
Properties
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 pictograms
GHS Signal word Warning
H315, H319, H335
P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Synthesis

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]

History

This acid was studied for the first time by Jacobus H. van 't Hoff in 1874.[2] 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.[3][4]

The compound has been considered as a renewable precursor to the commodity chemical methacrylic acid.[5]

References

  1. R. L. Shriner, S. G. Ford, L. J. Roll (1931). "Mesaconic Acid". Org. Synth. 11: 74. doi:10.15227/orgsyn.011.0074.CS1 maint: uses authors parameter (link)
  2. "Mesaconic acid". Mesaconic acid. Archived from the original on November 17, 2005. Retrieved September 8, 2005.
  3. "Barker, Horace Albert". The Stadtman Way: The Story of Two Biochemists at NIH. Office of NIH History. Retrieved December 21, 2011.
  4. Switzer, Robert L.; Stadtman, Earl R.; Stadtman, Thressa C. (2004). "H.A. Barker". Biographical Memoirs. National Academies Press. 84: 3–22. Retrieved December 21, 2011.
  5. 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: 199–215. doi:10.1016/j.eurpolymj.2017.11.002.CS1 maint: uses authors parameter (link)
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