Mesaconic acid

Mesaconic acid
IUPAC name (2E)-2-Methyl-2-butenedioic acid
Identifiers
CAS number	498-24-8
Jmol-3D images	Image 1
SMILES OC(/C(C)=C/C(O)=O)=O
Properties
Molecular formula	C5H6O4
Molar mass	130.10 g/mol
Density	1.31 g/cm3
Melting point	204-205 °C
Boiling point	250 °C (decomp.)
Y acid (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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

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

• "Mesaconic acid". Mesaconic acid. Archived from the original on November 17, 2005. http://web.archive.org/web/20051117102410/http://dbhs.wvusd.k12.ca.us/webdocs/Chem-History/Van't-Hoff-1874.html. Retrieved September 8, 2005. 
• "The Stadtman Way". Horace Albert Barker. http://www.history.nih.gov/exhibits/stadtman/bios.htm#Barker. Retrieved September 8, 2005. 
• "The National Academies Press". Biographical Memoirs V.84 (2004). http://lab.nap.edu/openbook/0309089573/html/14.html. Retrieved September 8, 2005. 
• Merck Index, 11th Edition, 5806.