Mesaconic acid
Encyclopedia
Mesaconic acid is one of several isomer
Isomer
In chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...

ic carboxylic acid
Carboxylic acid
Carboxylic acids are organic acids characterized by the presence of at least one carboxyl group. The general formula of a carboxylic acid is R-COOH, where R is some monovalent functional group...

s obtained from citric acid
Citric acid
Citric acid is a weak organic acid. It is a natural preservative/conservative and is also used to add an acidic, or sour, taste to foods and soft drinks...

. It is the trans-isomer of citraconic acid
Citraconic acid
Citraconic acid is one of the pyrocitric acids formed upon the heating of citric acid. It is the cis-isomer of mesaconic acid....

. It is used as a fire retardant
Fire
Fire is the rapid oxidation of a material in the chemical process of combustion, releasing heat, light, and various reaction products. Slower oxidative processes like rusting or digestion are not included by this definition....

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History

This acid was studied for the first time by Dutch
Netherlands
The Netherlands is a constituent country of the Kingdom of the Netherlands, located mainly in North-West Europe and with several islands in the Caribbean. Mainland Netherlands borders the North Sea to the north and west, Belgium to the south, and Germany to the east, and shares maritime borders...

 chemist
Chemist
A chemist is a scientist trained in the study of chemistry. Chemists study the composition of matter and its properties such as density and acidity. Chemists carefully describe the properties they study in terms of quantities, with detail on the level of molecules and their component atoms...

 Jacobus H. van 't Hoff
Jacobus Henricus van 't Hoff
Jacobus Henricus van 't Hoff, Jr. was a Dutch physical and organic chemist and the first winner of the Nobel Prize in chemistry. He is best known for his discoveries in chemical kinetics, chemical equilibrium, osmotic pressure, and stereochemistry...

 in 1874. Later American
United States
The United States of America is a federal constitutional republic comprising fifty states and a federal district...

 biochemist
Biochemist
Biochemists are scientists who are trained in biochemistry. Typical biochemists study chemical processes and chemical transformations in living organisms. The prefix of "bio" in "biochemist" can be understood as a fusion of "biological chemist."-Role:...

 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
Vitamin B12
Vitamin B12, vitamin B12 or vitamin B-12, also called cobalamin, is a water-soluble vitamin with a key role in the normal functioning of the brain and nervous system, and for the formation of blood. It is one of the eight B vitamins...

 coenzymes synthesis.

Recent studies revealed this acid is a competitive inhibitor
Enzyme
Enzymes are proteins that catalyze chemical reactions. In enzymatic reactions, the molecules at the beginning of the process, called substrates, are converted into different molecules, called products. Almost all chemical reactions in a biological cell need enzymes in order to occur at rates...

 of fumarate reduction
Redox
Redox reactions describe all chemical reactions in which atoms have their oxidation state changed....

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