Structure of Fumaric Acid
Fumaric acid, trans-2-butenedioic acid (also called trans-1, 2-Ethylene-dicarboxylic acid), is a white powder. Fumaric acid was first isolated from the plant Fumaria officinalis (Common Fumitory or Earth Smoke). It is used currently mostly in foods, but offers promising prospects in the area of medicine, cattle feed, and textiles.
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Medical Use
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Fumaric acid is produced in human skin by exposure to sunlight. It has been proposed that psoriasis may prevent this natural process from occurring, and that esters of fumaric acid may be useful in treating it. Since fumaric acid is somewhat toxic, such use should be done under the care of a medical professional.
Human Food Use
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Fumaric acid may be added to food products as an acidity regulator (Food Additive Number E297). In one application of this, fumaric acid may be used in baking powders as part of the acid component, in place of tartaric acid.
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Cattle Food
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Fumaric acid is being considered as a supplement to cattle feed, as scientific studies indicate it greatly reduces methane (a greenhouse gas) emission by cows (about 70% less).
Use in the Textile Industry
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Fumaric acid may be used in the manufacture of unsaturated polyester resins, because of its di-acid functionality, and its reactivity with the di-alcohol functionality of glycols.
It may also be used as a mordant in dyeing.
Sources
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Fumaric acid is made chemically from maleic acid anhydride, which itself is produced from butane. Do to the rising costs of petroleum products, however, a previously used process may come back into vogue, involving the fermentation of sugar by rhizopus and other fungi strains. Also being studied is its preparation by the fermentation of corn.
Fumaric acid exists naturally in many fruits and vegetables.
Chemical Structure
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A double bond imparts rigidity to the location of the four atoms attached to the two carbons, and is said to be "unsaturated". This means two more atoms of hydrogen could be added, if conditions were right for it.
Possessing one hydrogen (H) and one carboxylic acid group (COOH) on each side of a lone carbon-carbon double bond, the placements relative to the double bond can be two hydrogens on one side of the double bond, and two carboxylic groups on the other side (cis) or one hydrogen and one carboxylic group on one side, and the same on the other side (trans). The cis-structure in this instance, is called maleic acid, while the trans-structure is fumaric acid (See Fig. 1).
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References
Resources
- Photo Credit Fumaria Officinalis; GNU Free Documentation License Version 1.2 - Photo by Carsten Niehaus
