Mesaconic acid

Last updated
Mesaconic acid
Mesaconic-acid-2D-skeletal.svg
Mesaconic-acid-3D-balls.png
Names
Preferred IUPAC name
(2E)-2-Methylbut-2-enedioic acid
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChemSpider
ECHA InfoCard 100.007.146 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-859-2
KEGG
PubChem CID
UNII
  • InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+ X mark.svgN
    Key: HNEGQIOMVPPMNR-NSCUHMNNSA-N X mark.svgN
  • 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:
GHS-pictogram-exclam.svg
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).
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Mesaconic acid is one of several isomeric carboxylic acids obtained from citric acid. It is a colorless solid.

Contents

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]

Related Research Articles

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<span class="mw-page-title-main">Citric acid</span> Weak organic acid

Citric acid is an organic compound with the chemical formula HOC(CO2H)(CH2CO2H)2. It is a colorless weak organic acid. It occurs naturally in citrus fruits. In biochemistry, it is an intermediate in the citric acid cycle, which occurs in the metabolism of all aerobic organisms.

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<span class="mw-page-title-main">Propionic acid</span> Carboxylic acid with chemical formula CH3CH2CO2H

Propionic acid is a naturally occurring carboxylic acid with chemical formula CH
3
CH
2
CO
2
H
. It is a liquid with a pungent and unpleasant smell somewhat resembling body odor. The anion CH
3
CH
2
CO
2
as well as the salts and esters of propionic acid are known as propionates or propanoates.

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<span class="mw-page-title-main">Fumaric acid</span> Organic compound

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4
H
2
O2−
4
ion (in solution). Fumaric acid is the trans isomer of butenedioic acid, while maleic acid is the cis isomer.

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<span class="mw-page-title-main">3,3'-Diaminobenzidine</span> Chemical compound

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<span class="mw-page-title-main">Maleic acid</span> Dicarboxylic acid

Maleic acid or cis-butenedioic acid is an organic compound that is a dicarboxylic acid, a molecule with two carboxyl groups. Its chemical formula is HO2CCH=CHCO2H. Maleic acid is the cis-isomer of butenedioic acid, whereas fumaric acid is the trans-isomer. It is mainly used as a precursor to fumaric acid, and relative to its parent maleic anhydride, which has many applications..

<span class="mw-page-title-main">Itaconic acid</span> Chemical compound

Itaconic acid, or methylidenesuccinic acid, is an organic compound. This dicarboxylic acid is a white solid that is soluble in water, ethanol, and acetone. Historically, itaconic acid was obtained by the distillation of citric acid, but currently it is produced by fermentation. The name itaconic acid was devised as an anagram of aconitic acid, another derivative of citric acid.

<span class="mw-page-title-main">Triflic acid</span> Chemical compound

Triflic acid, the short name for trifluoromethanesulfonic acid, TFMS, TFSA, HOTf or TfOH, is a sulfonic acid with the chemical formula CF3SO3H. It is one of the strongest known acids. Triflic acid is mainly used in research as a catalyst for esterification. It is a hygroscopic, colorless, slightly viscous liquid and is soluble in polar solvents.

Ethanol, an alcohol found in nature and in alcoholic drinks, is metabolized through a complex catabolic metabolic pathway. In humans, several enzymes are involved in processing ethanol first into acetaldehyde and further into acetic acid and acetyl-CoA. Once acetyl-CoA is formed, it becomes a substrate for the citric acid cycle ultimately producing cellular energy and releasing water and carbon dioxide. Due to differences in enzyme presence and availability, human adults and fetuses process ethanol through different pathways. Gene variation in these enzymes can lead to variation in catalytic efficiency between individuals. The liver is the major organ that metabolizes ethanol due to its high concentration of these enzymes.

<span class="mw-page-title-main">Methylmalonyl-CoA</span> Chemical compound

Methylmalonyl-CoA is the thioester consisting of coenzyme A linked to methylmalonic acid. It is an important intermediate in the biosynthesis of succinyl-CoA, which plays an essential role in the tricarboxylic acid cycle. The compound is sometimes referred to as "methylmalyl-CoA".

<span class="mw-page-title-main">Iodine oxide</span> Class of chemical compounds

Iodine oxides are chemical compounds of oxygen and iodine. Iodine has only two stable oxides which are isolatable in bulk, iodine tetroxide and iodine pentoxide, but a number of other oxides are formed in trace quantities or have been hypothesized to exist. The chemistry of these compounds is complicated with only a few having been well characterized. Many have been detected in the atmosphere and are believed to be particularly important in the marine boundary layer.

<span class="mw-page-title-main">Citraconic acid</span> Chemical compound

Citraconic acid is an organic compound with the formula CH3C2H(CO2H)2. It is a white solid. The alkene is cis. The related trans alkene is called mesaconic acid. It is one of the pyrocitric acids formed upon the heating of citric acid. Citraconic acid can be produced, albeit inefficiently, by oxidation of xylene and methylbutanols. The acid displays the unusual property of spontaneously forming the anhydride, which, unlike maleic anhydride, is a liquid at room temperature.

<span class="mw-page-title-main">Itaconic anhydride</span> Chemical compound

Itaconic anhydride is the cyclic anhydride of itaconic acid and is obtained by the pyrolysis of citric acid. It is a colourless, crystalline solid, which dissolves in many polar organic solvents and hydrolyzes forming itaconic acid. Itaconic anhydride and its derivative itaconic acid have been promoted as biobased "platform chemicals" and bio- building blocks.) These expectations, however, have not been fulfilled.

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. National Academies Press. 84: 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 .