Fumaric acid

Fumaric acid is an organic compound with the formula HO2CCH=CHCO2H[1]. It is a white solid that occurs naturally and has a fruit-like taste. Fumaric acid is used as a food additive, particularly as an acidity regulator, and is denoted by the E number E297[1]. It is approved for use in the EU, USA, Australia, and New Zealand[1].

Biosynthesis and Occurrence

Fumaric acid is produced in eukaryotic organisms from succinate in complex 2 of the electron transport chain via the enzyme succinate dehydrogenase[1]. It is found in various natural sources, including fumitory (Fumaria officinalis), bolete mushrooms (Boletus fomentarius var. pseudo-igniarius), lichen, and Iceland moss[1]. Human skin also naturally produces fumaric acid when exposed to sunlight[1].

Uses

Food

Fumaric acid has been used as a food acidulant since 1946 and is used in beverages and baking powders to add sourness[1]. It is also used in the making of wheat tortillas as a food preservative and as the acid in leavening[1].

Medicine

Fumaric acid was developed as a medicine to treat the autoimmune condition psoriasis in the 1950s in Germany[1]. The ester dimethyl fumarate has been used to treat multiple sclerosis, as it activates the Nrf2 antioxidant response pathway[1].

Other Uses

Fumaric acid is used in the manufacture of polyester resins and polyhydric alcohols and as a mordant for dyes[1]. It is also used to reduce methane production in lambs[1].

Synthesis

Fumaric acid is produced based on catalytic isomerisation of maleic acid in aqueous solutions at low pH[1]. It precipitates from the reaction solution[1].

Safety and Handling

Fumaric acid can affect health when breathed in, and contact can irritate and burn the skin and eyes[3]. Breathing it in can irritate the nose and throat, causing coughing and wheezing, and it may damage the kidneys[3]. It is combustible and prohibited where it is used, handled, or stored in a manner that could create a potential fire or explosion hazard[3].

Citations:

[1] https://en.wikipedia.org/wiki/Fumaric_acid

[2] https://go.drugbank.com/drugs/DB01677

[3] https://nj.gov/health/eoh/rtkweb/documents/fs/0949.pdf

[4] https://www.sigmaaldrich.com/US/en/product/sial/47910

[5] https://pubchem.ncbi.nlm.nih.gov/compound/Fumaric-Acid