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11-SEPTEMBER-2008 13:54:10 - Fumaric acid Redirected from Fumarate Fumaric acid Skeletal formula of fumaric acid Ball-and-stick model of the fumaric acid molecule IUPAC name E-Butenedioic acid Other names trans-1,2-Ethylenedicarboxylic acid 2-Butenedioic acid Allomaleic acid Boletic acid Lichenic acid Identifiers CAS number 110-17-8 EINECS number 203-743-0 SMILES OC=OC=CC=OO Properties Molecular formula C4H4O4 Molar mass 116.07 g/mol Appearance White solid Density 1.635 g/cm³, solid Melting point 287 °C Solubility in water 0.63 g/100 mL Acidity pKa pka1 = 3.03, pka2 = 4.44 Hazards EU classification Irritant Xi R-phrases R36 S-phrases S2 S26 Related compounds Related carboxylic acids Maleic acid Succinic acid Related compounds Fumaryl chloride Fumaronitrile Dimethyl fumarate IronII fumarate Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references Fumaric acid is the chemical compound with the formula HO2CCH=CHCO2H. This colorless crystalline compound is one of two isomeric unsaturated dicarboxylic acids, the other being maleic acid wherein the carboxylic acid groups are cis. It has a fruit-like taste. The salts and esters of fumaric acid are known as fumarates. Fumaric acid, when added to food products, is denoted by E number E297. Contents 1 Biology 2 Medicine 3 Food 4 Chemistry 5 Other uses 6 Safety 7 See also 8 References 9 External links Biology Fumaric acid is found in fumitory Fumaria officinalis, bolete mushrooms specifically Boletus fomentarius var. pseudo-igniarius, lichen, and Iceland moss. Fumarate is an intermediate in the citric acid cycle used by 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 malate. Human skin naturally produces fumaric acid when exposed to sunlight.citation needed Fumarate is also a byproduct of the urea cycle. Medicine Fumaric acid esters 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.citation needed A starting dose is 60-105 mg daily, which may be gradually increased to as much as 1,290 mg per day. Side-effects include kidney or gastrointestinal disorders, as well as skin flushing; these are mainly caused by excess intake. Decreased white blood cell counts have been reported with prolonged use.citation needed Food Fumaric acid is a food acidulent used since 1946 because it is non-toxic. It is generally used in beverages and baking powders 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.1 A traditional synthesis involves oxidation of furfural from the processing of maize using sodium chlorate in the presence of a vanadium-based catalyst.2 Nowadays industrial synthesis of fumaric acid is mostly based on catalytic isomerisation of maleic acid which in turn is accessible in large volumes as a hydrolysis product of maleic anhydride, produced by catalytic oxidation of benzene or butane in aqueous solutions.3 The chemical properties of fumaric acid can be anticipated from its component functional groups. This weak acid forms a diester, it undergoes additions across the double bond, and it is an excellent dienophile. Other uses Fumaric acid is used in the manufacture of polyester resins and polyhydric alcohols 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 ^ Volhard, J. Darstellung von Maleïnsäureanhydrid Justus Liebig's Annalen der Chemie 1892, volume 268, page 255-6. DOI: 10.1002/jlac.18922680108 ^ Milas, N. A. Fumaric Acid Organic Synthesis 1943, Collective Volume 2, page 302. Online version ^ British Patent No. 775,912, publicated on the May 29, 1957, by Monsanto Chemical Company. External links International Chemical Safety Card 1173 v d e Citric Acid Cycle Metabolic Pathway Oxaloacetate Malate Fumarate Succinate Succinyl-CoA Acetyl-CoA NADH + H+ NAD+ H2O FADH2 FAD CoA + ATPGTP Pi + ADPGDP + H2O NADH + H+ + CO2 CoA NAD+ H2O H2O NADP+ NADPH + H+ CO2 Citrate cis-Aconitate Isocitrate Oxalosuccinate α-Ketoglutarate v d e Antipsoriatics D05 Topical: tars Tar Topical: antracens Dithranol Topical: psoralens Trioxysalen - Methoxsalen Topical: other Fumaric acid - vitamin D Calcipotriol, Calcitriol, Tacalcitol - Tazarotene Systemic: psoralens Trioxysalen - Methoxsalen - Bergapten Systemic: retinoids Etretinate - Acitretin Retrieved from http://en..org/wiki/Fumaric_acid Categories: Citric acid cycle | Dicarboxylic acids | Food additives | Food acidity regulatorsHidden categories: All articles with statements | Articles with statements since November 2007 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Dansk Deutsch Español Français Italiano Latviešu Magyar Nederlands 日本語 Polski Português Simple English Suomi Svenska 中文 This page was last modified on 4 August 2008, at 18:59
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