Fumaric acid

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Fumaric acid
Image:Fumaric acid.svg
General
Common name	fumaric acid
Systematic name	(E)-butenedioic acid
Other names	trans-1,2-ethylenedicarboxylic acid
Molecular formula	C₄H₄O_{4 Simplified molecular input line entry specification\|SMILES]]}	OC(=O)C=CC(=O)O
Molar mass	116.07 g/mol
Appearance	white solid
CAS number	[110-17-8]
Properties
Density and phase	1.635 g/cm³, solid
Solubility in water	0.63g/100ml
Solubility in ethanol	Soluble
Melting point	300–2 °C subl.
Acidity (pK_a)	?
Thermodynamic data
Standard enthalpy of formation Δ_fH°_solid	? kJ/mol
Standard enthalpy of combustion Δ_cH°_solid	? kJ/mol
Standard molar entropy S°_solid	? J.K⁻¹.mol⁻¹
Hazards
EU classification	Irritant (Xi)
R-phrases	R36
S-phrases	S2, S26
NFPA 704
Supplementary data page
Structure and properties	n, ε_r, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Regulatory data	Flash point, RTECS number, etc.
Related compounds
Related carboxylic acids	Maleic acid Succinic acid
Related compounds	Fumaryl chloride Fumaronitrile Dimethyl fumarate Iron(II) fumarate
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Fumaric acid (IUPAC systematic name: 2-butenedioic acid), also called allomaleic acid, boletic acid or lichenic acid, is a colorless crystalline flammable carboxylic acid based on butene and molecular formula C₄H₄O₄. Irritating maleic anhydride fumes are produced by its combustion. Having a fruitlike taste, it is found in fumitory (Fumaria officinalis), bolete mushrooms (specifically Boletus fomentarius var. pseudo-igniarius), lichen, and Iceland moss.

Fumaric acid is an acid used in the manufacture of polyester resins and polyhydric alcohols, as a mordant for dyes, or as a flavoring. It is a common component of food additives and dietary supplements, and is sometimes used as a substitute for tartaric acid in beverages or baking powder.

1 Biology
2 Medicine
3 Food
4 See also
5 References
6 External links

[edit] Biology

Related to malic acid, fumaric acid is used by cells to produce energy from food. Human skin naturally produces fumaric acid when exposed to sunlight.

[edit] 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. A starting dose is 60-105mg daily, which may be gradually increased to as much as 1,290mg 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.

[edit] Food

Fumaric acid is a food acidulant used since 1946 because it is non-toxic. It is generally used in beverages and baking powders for which requirements are placed on purity, such as Welch's Grape Drink. 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.