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'''Fumaric
</ref> The [[salt (chemistry)|salts]] and [[ester]]s are known as '''fumarates'''. Fumarate can also refer to the {{chem|C|4|H|2|O|4|2−}} ion (in solution).▼
==Biosynthesis and occurrence==
It is produced in [[eukaryotic]] organisms from [[succinate]] in complex 2 of the electron transport chain via the [[enzyme]] [[succinate dehydrogenase]]. It is one of two [[cis-trans isomerism|isomeric]] unsaturated [[dicarboxylic acid]]s, the other being [[maleic acid]]. In fumaric acid the carboxylic acid groups are ''trans'' (''E'') and in maleic acid they are ''cis'' (''Z'').
Fumaric acid is found in [[fumitory]] (''Fumaria officinalis''), [[bolete]] [[mushroom]]s (specifically ''Boletus fomentarius var. pseudo-igniarius''), [[lichen]], and [[Iceland moss]].▼
▲The [[salt (chemistry)|salts]] and [[ester]]s are known as '''fumarates'''. Fumarate can also refer to the {{chem|C|4|H|2|O|4|2−}} ion (in solution).
Fumarate is an [[Reaction intermediate|intermediate]] in the [[citric acid cycle]] used by [[cell (biology)|cells]] to produce energy in the form of [[adenosine triphosphate]] (ATP) from [[food]]. It is formed by the [[oxidation]] of [[succinate]] by the enzyme [[succinate dehydrogenase]]. Fumarate is then converted by the enzyme [[fumarase]] to [[malic acid|malate]].▼
Human skin naturally produces fumaric acid when exposed to [[sunlight]].<ref>[https://books.google.com/books?id=tWJLUWT06BEC&pg=PA159&dq=Human+skin+fumaric+acid&hl=en&sa=X&ei=6eYiVbu5FIKhgwTIlYCgCA&ved=0CCMQ6AEwAQ#v=onepage&q=Human%20skin%20fumaric%20acid&f=false Active Ingredients Used in Cosmetics: Safety Survey], Council of Europe. Committee of Experts on Cosmetic Products</ref><ref>{{Cite news|url=http://healthyeating.sfgate.com/fumaric-acid-foods-12220.html|title=Fumaric Acid Foods|access-date=2018-04-22|language=en}}</ref>▼
Fumarate is also a product of the [[urea cycle]].▼
{{TCACycle_WP78|highlight=Fumaric_acid}}▼
==Uses==
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===Other uses===
Fumaric acid is used in the manufacture of [[polyester]] [[resin]]s and [[polyhydric alcohol]]s and as a [[mordant]] for dyes.
When fumaric acid is added to their feed, lambs produce up to 70% less methane during digestion.<ref>{{Cite news | url = https://m.phys.org/news/2008-03-scientists-cow-flatulence.html | title = Scientists look to cut cow flatulence | date = March 21, 2008 | publisher = phys.org }}</ref>
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It is "practically non-toxic" but high doses are probably [[Nephrotoxicity|nephrotoxic]] after long-term use.<ref name=ecscfa>European Commission: {{cite web |url=http://ec.europa.eu/food/fs/sc/scan/out112_en.pdf |title=European Commission Report of the Scientific Committee on Animal Nutrition on the Safety of Fumaric Acid |accessdate=2014-03-07}}</ref>
==Synthesis and reactions==
Fumaric acid was first prepared from [[succinic acid]].<ref>Volhard, J. "Darstellung von Maleïnsäureanhydrid" Justus Liebig's Annalen der Chemie 1892, volume 268, page 255-6. {{doi|10.1002/jlac.18922680108}}</ref> A traditional synthesis involves oxidation of [[furfural]] (from the processing of [[maize]]) using [[sodium chlorate|chlorate]] in the presence of a [[vanadium]]-based [[catalyst]].<ref>Milas, N. A. "Fumaric Acid" ''Organic Synthesis'' 1943, Collective Volume 2, page 302. [http://www.orgsyn.org/orgsyn/pdfs/CV2P0302.pdf Online version]</ref>
Currently, industrial synthesis of fumaric acid is mostly based on [[catalyst|catalytic]] [[isomerisation]] of [[maleic acid]] in aqueous solutions at low p''H''. Maleic acid is accessible in large volumes as a [[hydrolysis]] product of maleic anhydride, produced by catalytic oxidation of [[benzene]] or [[butane]].<ref
The chemical properties of fumaric acid can be anticipated from its component [[functional group]]s. This weak acid forms a di[[ester]], it undergoes additions across the [[alkene|double bond]], and it is an excellent [[dienophile]].
Fumaric acid does not combust in a [[bomb calorimeter]] under conditions where [[maleic acid]] deflagrates smoothly. For teaching experiments designed to measure the difference in energy between the cis- and trans- isomers, a measured quantity of carbon can be ground with the subject compound and the enthalpy of combustion computed by difference.
▲Fumaric acid is found in [[fumitory]] (''Fumaria officinalis''), [[bolete]] [[mushroom]]s (specifically ''Boletus fomentarius var. pseudo-igniarius''), [[lichen]], and [[Iceland moss]].
▲Fumarate is an [[Reaction intermediate|intermediate]] in the [[citric acid cycle]] used by [[cell (biology)|cells]] to produce energy in the form of [[adenosine triphosphate]] (ATP) from [[food]]. It is formed by the [[oxidation]] of [[succinate]] by the enzyme [[succinate dehydrogenase]]. Fumarate is then converted by the enzyme [[fumarase]] to [[malic acid|malate]].
▲Human skin naturally produces fumaric acid when exposed to [[sunlight]].<ref>[https://books.google.com/books?id=tWJLUWT06BEC&pg=PA159&dq=Human+skin+fumaric+acid&hl=en&sa=X&ei=6eYiVbu5FIKhgwTIlYCgCA&ved=0CCMQ6AEwAQ#v=onepage&q=Human%20skin%20fumaric%20acid&f=false Active Ingredients Used in Cosmetics: Safety Survey], Council of Europe. Committee of Experts on Cosmetic Products</ref><ref>{{Cite news|url=http://healthyeating.sfgate.com/fumaric-acid-foods-12220.html|title=Fumaric Acid Foods|access-date=2018-04-22|language=en}}</ref>
▲Fumarate is also a product of the [[urea cycle]].
▲{{TCACycle_WP78|highlight=Fumaric_acid}}
==See also==
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