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| Fumaric acid | |
|---|---|
| General | |
| Common name | fumaric acid |
| Systematic name | (E)-butenedioic acid |
| Other names | trans-1,2-ethylenedicarboxylic acid |
| Molecular formula | trans-HOOCCH=CHCOOH |
| SMILES | OC(=O)C=CC(=O)O |
| Molar mass | 116.07 g/mol |
| Appearance | white solid |
| CAS number | * |
| 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 (pKa) | ? |
| Thermodynamic data | |
| Standard enthalpy of formation ΔfH°solid | ? kJ/mol |
| Standard enthalpy of combustion ΔcH°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, εr, 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) Chemical infobox | |
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.
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.
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.
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.
See also
- Dermatology
- Photosynthesis
- Maleic acid, the cis-isomer of fumaric acid
Sources
- http://www.shreeadditives.com/htmlsite/3d.htm
External links
Dicarboxylic acids | Food additives
Fumarsäure | Acide fumarique | Fumaarzuur | フマル酸 | Kwas fumarowy | Ácido fumárico
"Fumaric acid"