Fumaric acid is one of the substances that are formed in the cells of humans and other animals in the process of natural metabolism. Its compounds are used in medicine, agriculture, food and chemical industries. In large quantities, this substance can cause negative reactions - allergies and gastrointestinal disorders.
General Description
Fumaric acid is an isomer of ethylene-1, 2-dicarboxylic acid in the trans configuration (has an arrangement of hydrocarbon substituents on opposite sides of the C-C double bond). For the first time this substance was obtained from succinic acid.
Empirical formula of fumaric acid: C4H4O4.
In appearance, the compound is a colorless, odorless crystalline powder.
The structural formula of fumaric acid is shown in the figure below:
Acid is found in many plants (European dodder, corydalis, poppy and others), lichens and fungi, and is also formed during the fermentation of carbohydrates inthe presence of the fungus Aspergillus fumigatus (aspergillus fumigatus).
Properties
The main physical and chemical properties of fumaric acid are as follows:
- Molecular weight – 116.07 a.u. e.m.
- Solubility: o in alcohols – good; o in water and diethyl ether - weak; o in organic solvents - insoluble.
- Melting point - 296.4 °С.
- Boiling point - 165 °C.
Fumaric and maleic acids are easily reduced to succinic acid. When oxidized with peroxide compounds, mesotartaric acid is formed, when interacting with alcohols, mono- and diesters (fumarates) occur.
Biochemistry
Fumaric acid is found in the blood of a he althy person at a concentration of up to 3 mg/l. It is formed as an intermediate in the tricarboxylic acid cycle, during the synthesis of urea and the oxidation of certain amino acids, and in human skin under the influence of ultraviolet radiation.
Fumarates play an important role in human tissues during their oxygen starvation. In combination with malic acid and glutamic acid s alts, they increase the content of ATP and glycogen, the main form of glucose storage, a universal source of energy for cells. In experiments on rats, it was found that this substance increases the duration of the contraction of the heart during its isolation. In hemorrhagic shock, fumarates help to increase the survival of animals.
Synthesis
Obtaining fumaric acid inindustrial scale is produced by catalytic isomerization of maleic acid in aqueous solution. In Russia, this technology is used to synthesize technical acid, which is not applicable in the food industry and pharmacy due to the presence of heavy metal s alts.
Highly purified food grade fumaric acid is made from malic or tartaric acid. This method of manufacturing a substance is associated with technical difficulties (requires labor-intensive multi-stage purification) and is more expensive. The quality of technical fumaric acid is more dependent on the purity of maleic acid, which is obtained from maleic and phthalic anhydrides.
Application
In the chemical industry, acid is used to produce the following substances:
- polyester resin;
- synthetic drying oils;
- plasticizers;
In the food industry (additive E297) it is used as an acidifier (a substitute for citric and tartaric acid) in the preparation of drinks, sweets and pastries. At the same time, its consumption is lower than that of analogues. Technical characteristics of the food additive are regulated in accordance with GOST 33269-2015.
Medicine
In medicine, this compound is used for the following purposes:
- dimethyl ether (dimethyl fumarate) - treatment of skin pathologies (psoriasis, lichen), multiple sclerosis, baldness, granulomatous diseases; fungicidal, antifungalremedy;
- fumaric acid sodium s alt - infusion preparations, crystalloid blood substitutes with antihypoxic, antioxidant action (used for gastroduodenal bleeding, peritonitis, severe thermal injuries, cardiac surgery, acute coronary syndrome, hypovolemia, extensive blood loss, intoxication);
- other derivatives - appetite enhancers, tranquilizers, radiopaque agents, rhinitis medications.
Among the drugs of the second group, Mafusol, Mexidol, Confumin and Polyoxyfumarin find the greatest practical application.
Clinical trials of fumaric acid preparations are also currently underway for the treatment of pathologies such as:
- malignant neoplasms;
- Huntington's chorea;
- HIV;
- malaria.
Experiments on animals have shown that a 1% acid solution taken with food for a long time significantly reduces the activity of carcinogens.
Fumaric acid reduces the acidity of the stomach and affects the microflora of the gastrointestinal tract. In the intestine, it creates a slightly acidic environment, which inhibits the growth of pathogenic bacteria and creates favorable conditions for the development of lacto-, bifidus- and acidobacteria. However, due to the difficulty of obtaining a highly purified acid for pharmaceutical purposes and in the production of dietary supplements, this compound is rarely used.
Agriculture
In ruralOn the farm, fumaric acid is used as an additive in pet food for the following functions:
- improving metabolism in stressful situations;
- increased feed digestibility, increased appetite;
- stimulating muscle recruitment, accelerating bone formation and egg formation in poultry (non-hormonal anabolic);
- increasing the body's defenses during the period of mass diseases and vaccination;
- normalization of the intestinal flora, prevention of fungal and bacterial diseases.
Fumaric acid causes accelerated formation of ATP, promotes the accumulation of nutrients and ascorbic acid, which is one of the main antioxidants.
He alth damage
High quality purified acid is safe for human he alth. The harm of fumaric acid is mainly due to the fact that unscrupulous manufacturers use a technical quality product containing toxic impurities of maleic acid and heavy metal s alts.
Dimethyl fumarate is also used as a cheap biocide to protect leather furniture and shoes from fungal infections during shipping. However, in this capacity, the acid can cause severe allergic skin reactions. So, in Finland and the UK, more than a thousand consumers demanded monetary compensation for harm to he alth when buying Chinese furniture. Since 2008, European countries have introduced a ban on the sale of shoes and furniture impregnated with dimethyl fumarate.
