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Fumaric acid was first prepared from succinic acid.[1] A traditional synthesis involves oxidation of furfural (from the processing of maize) using chlorate in the presence of a vanadium-based catalyst.[2] Currently, industrial synthesis of fumaric acid is mostly based on catalytic isomerisation of maleic acid in aqueous solutions at low pH. Maleic acid is accessible in large volumes as a hydrolysis product of maleic anhydride, produced by catalytic oxidation of benzene or butane.[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.

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.

Food[edit]

As a food additive, it is used as an acidity regulator and is denoted by the E number E297. Fumaric acid is a food acidulent used since 1946. 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 to add sourness, similar to the way malic acid is used. It is also used as a coagulant in stovetop pudding mixes.

It is approved for use as a food additive in the EU,[4] USA[5] and Australia and New Zealand[6] (where it is listed by its INS number 297).

Medicine[edit]

In patients with relapsing-remitting multiple sclerosis, dimethyl fumarate (BG-12, Biogen) significantly reduced relapse and disability progression in a phase 3 trial. It activates the Nrf2 antioxidant response pathway, the primary cellular defense against the cytotoxic effects of oxidative stress.[7]

Other uses[edit]

Fumaric acid is used in the manufacture of polyester resins and polyhydric alcohols and as a mordant for dyes.