Fumaric acid

Fumaric acid or trans-butenedioic acid is the chemical compound with the formula HO2CCH=CHCO2H. Fumaric acid has a fruit-like taste and has been used as a food acidulant since 1946. Its E number is E297.Acetyl-CoAOxaloacetateMalateFumarateSuccinateSuccinyl-CoACitratecis-AconitateIsocitrateOxalosuccinate2-oxoglutarateL-citrullineCarbamoylphosphateL-ornithineL-aspartateUreaL-argininosuccinateL-arginineFumarate Fumaric acid or trans-butenedioic acid is the chemical compound with the formula HO2CCH=CHCO2H. Fumaric acid has a fruit-like taste and has been used as a food acidulant since 1946. Its E number is E297. 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 isomeric unsaturated dicarboxylic acids, the other being maleic acid. In fumaric acid the carboxylic acid groups are trans (E) and in maleic acid they are cis (Z). The salts and esters are known as fumarates. Fumarate can also refer to the C4H2O2−4 ion (in solution). Fumaric acid has been used as a food acidulant since 1946. It is approved for use as a food additive in the EU, USA and Australia and New Zealand. As a food additive, it is used as an acidity regulator and can be denoted by the E number E297. It is generally used in beverages and baking powders for which requirements are placed on purity. Fumaric acid is used in the making of wheat tortillas as a food preservative and as the acid in leavening. It is generally used as a substitute for tartaric acid and occasionally in place of citric acid, at a rate of 1 g of fumaric acid to every ~1.5 g of citric acid, in order to add sourness, similarly to the way malic acid is used. As well as being a component of some artificial vinegar flavors, such as 'Salt and Vinegar' flavored potato chips, it is also used as a coagulant in stove-top pudding mixes. The European Commission Scientific Committee on Animal Nutrition, part of DG Health, found in 2014 that fumaric acid is 'practically non-toxic' but high doses are probably nephrotoxic after long-term use. In patients with relapsing-remitting multiple sclerosis, the ester 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. Various fumaric acid esters (FAES) have specific immunomodulating (respectively moderate immunosuppression) properties which are responsible for certain effects in the treatment of psoriasis. In the Netherlands, Germany, Austria and the Benelux countries substances derived from fumaric acid have been used for half a century for this purpose. Although it seems that a certain effectiveness exists (and many studies have confirmed the effect), more statistically powerful studies are necessary to provide better evidence of the effectiveness of fumaric acid esters in treatment of psoriasis (e.g. more accurate in terms of the dermatological nosology of this autoimmune disease). Such studies should in the future help specify which psoriasis variants (in terms of the course, the immunological profile of the patient etc.) are suited to be treated with fumaric acid esters. Fumaric acid is present in the herb called Fumaria officinalis. In Sicily, the top of this herb has been used to treat various skin disorders including psoriasis. Baths with this herb have been used there for several centuries. Fumaric acid is used in the manufacture of polyester resins and polyhydric alcohols and as a mordant for dyes.Since the early 21st century, it has been used to synthesize one of the first metal-organic frameworks presenting commercial applications thanks to its remarkable adsorption and mechanical properties, combined with a low toxicity compared to other well-studied MOFs.