Mesaconic acid

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Mesaconic acid
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
(2E)-2-Methylbut-2-enedioic acid
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChemSpider
EC Number
  • 207-859-2
KEGG
UNII
  • InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+ ☒N
    Key: HNEGQIOMVPPMNR-NSCUHMNNSA-N ☒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
  • OC(/C(C)=C/C(O)=O)=O
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 labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
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).

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

  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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