Mesaconic acid

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Mesaconic acid
Skeletal formula
Ball-and-stick model
Names
IUPAC name
(2E)-2-Methyl-2-butenedioic acid
Identifiers
498-24-8 YesY
ChEBI CHEBI:CHEBI:16600 N
ChemSpider 10289044 N
EC number 207-859-2
Jmol-3D images Image
KEGG C01732 N
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)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Mesaconic acid is one of several isomeric carboxylic acids obtained from citric acid. It is the trans-isomer of citraconic acid. It is used as a fire retardant.

History[edit]

This acid was studied for the first time by Dutch chemist Jacobus H. van 't Hoff in 1874. Later American biochemist Horace Albert Barker and his team successfully isolated this acid from fermenting bacterium Clostridium tetanomorphum in 1950s. Further studies led him to discover this organic compound was involved in vitamin B12 coenzymes synthesis.

Recent studies revealed this acid is a competitive inhibitor of fumarate reduction.


References[edit]

  • "Mesaconic acid". 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 (National Academies Press) 84: 3–22. Retrieved December 21, 2011. 
  • Merck Index, 11th Edition, 5806.