Fumaric acid
839112
214717876
2008-05-24T23:17:36Z
Aly89
4393236
Redirected succinic acid link to it's page instead of bromosuccinic which infact doesn't exist
{{Chembox new
| Name = Fumaric acid
| ImageFile = Fumaric-acid-2D-skeletal.png
| ImageSize = 200px
| ImageName = Skeletal formula of fumaric acid
| ImageFile1 = Fumaric-acid-3D-balls.png
| ImageSize1 = 200px
| ImageName1 = Ball-and-stick model of the fumaric acid molecule
| IUPACName = (E)-Butenedioic acid
| OtherNames = ''trans''-1,2-Ethylenedicarboxylic acid<br />2-Butenedioic acid<br />Allomaleic acid<br />Boletic acid<br />Lichenic acid
| Section1 = {{Chembox Identifiers
| SMILES = OC(=O)C=CC(=O)O
| CASNo = 110-17-8
| EINECS = 203-743-0
| CoE = 25
| FEMA = 2488
| JECFA = 618
| FDA = 172.350
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>4</sub>H<sub>4</sub>O<sub>4
| MolarMass = 116.07 g/mol
| Appearance = White solid
| Density = 1.635 g/cm³, solid
| Solubility = 0.63 g/100 mL
| MeltingPt = 287 °C
| pKa = p''k''<sub>a1</sub> = 3.03, p''k''<sub>a2</sub> = 4.44
}}
| Section7 = {{Chembox Hazards
| EUClass = Irritant ('''Xi''')
| RPhrases = {{R36}}
| SPhrases = {{S2}} {{S26}}
}}
| Section8 = {{Chembox Related
| Function = [[carboxylic acid]]s
| OtherFunctn = [[Maleic acid]]<br />[[Succinic acid]]
| OtherCpds = [[Fumaryl chloride]]<br />[[Fumaronitrile]]<br />[[Dimethyl fumarate]]<br />[[Iron(II) fumarate]]
}}
}}
'''Fumaric acid''' is the [[chemical compound]] with the formula HO<sub>2</sub>CCH=CHCO<sub>2</sub>H. This [[color]]less [[crystal]]line compound is one of two isomeric unsaturated [[dicarboxylic acid]]s, the other being [[maleic acid]] wherein the carboxylic acid groups are cis. It has a [[fruit]]-like [[taste]]. The [[salt (chemistry)|salts]] and [[ester]]s of fumaric acid are known as '''fumarates'''.
Fumaric acid, when added to food products, is denoted by [[E number]] E297.
==Biology==
Fumaric acid is found in [[fumitory]] (''Fumaria officinalis''), [[bolete]] [[mushroom]]s (specifically ''Boletus fomentarius var. pseudo-igniarius''), [[lichen]], and [[Iceland moss]].
Fumarate is an 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]].{{Fact|date=November 2007}}
Fumarate is also a byproduct of the [[urea cycle]].
==Medicine==
Fumaric acid [[ester]]s are sometimes used to treat [[psoriasis]], as it has been suggested that the condition is caused by an impairment of fumaric acid production in the skin.{{Fact|date=November 2007}} A starting [[medication|dose]] is 60-105 mg daily, which may be gradually increased to as much as 1,290 mg per day. [[Adverse drug reaction|Side-effects]] include [[kidney]] or [[gastrointestinal]] disorders, as well as skin [[Flushing (physiology)|flushing]]; these are mainly caused by excess intake. Decreased [[white blood cell]] counts have been reported with prolonged use.{{Fact|date=November 2007}}
==Food==
Fumaric acid is a food acidulent used since 1946 because it is non-toxic. It is generally used in beverages and [[baking powder]]s for which requirements are placed on purity. It is generally used as a substitute for [[tartaric acid]] and occasionally in place of [[citric acid]], at a rate of 1.36 g of citric acid to every 0.91 grams of fumaric acid for the same taste. It is also used in candy to add sourness, similar to the way [[malic acid]] is used.
==Chemistry==
Fumaric acid is inexpensive, so it is typically purchased rather than prepared. It was first prepared from [[Succinic acid| 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]] 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>
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]].
==Other uses==
Fumaric acid is used in the manufacture of [[polyester]] [[resin]]s and [[polyhydric alcohol]]s and as a [[mordant]] for dyes.
==Safety==
Fumaric acid converts to the irritant [[maleic anhydride]], upon partial combustion.
==See also==
*[[Dermatology]]
*[[Photosynthesis]]
*[[Maleic acid]], the cis-isomer of fumaric acid
==References==
<references/>
==External links==
*[http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc11/icsc1173.htm International Chemical Safety Card 1173]
{{citric acid cycle}}
{{Antipsoriatics}}
[[Category:Dicarboxylic acids]]
[[Category:Food additives]]
[[Category:Food acidity regulators]]
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