Fumaric acid, also known as fumaric acid, fumaric acid, or lichenic acid, fumaric acid (IUPAC name (E)-butenedicarboxylic acid), is a colorless, flammable crystal, Carboxylic acids derived from butenes. Its chemical formula is C4H4O4. Burning fumaric acid releases irritating maleic anhydride smoke. It tastes like fruit and can be found in the genus Corydalis, Boletus, lichens, and Icelandic seaweed.
ã€Chinese name】Fumarate
[Chinese alias] fumaric acid; (E)-2-butenedioic acid; trans-1,2-ethylene dihydroxy acid; fumaric acid; purpuric acid; E)-2-butene II; Diacid (fumaric acid); Butenoic acid, trans; Fumaric acid; 1,2-Ethylene dicarboxylic acid; Butylene diacid (fumaric acid); Fumaric acid/Fumaric acid; Acid;fumaric acid;fumaric acid;E-butenedicarboxylic acid;fumaric acid FUMARIC ACID
[English alias] 2-BUTENEDIOIC ACID; ACIDUM FUMARICUM; (e)-1,2-ethenedicarboxylic acid; (E)-2-Butenedioic acid; FA; FEMA 2488; LICHENIC ACID; RARECHEM AL BO 0142; TRANS-1, 2 -ETHYLENEDICARBOXYLIC ACID; TRANS-1,2-ETHYLENTRICARBOXYLIC ACID; TRANS-2-BUTEN-1,4-DIOIC ACID; TRANS-2-BUTENEDIOIC ACID; TRANS-BUTENEDICARBOXYLIC ACID; TRANS-BUTENEDIOIC ACID; (2E)-2-Butenedioic Acid; (e)-2-butenedioicaci; (e)-butenedioicaci; (E)-HO2CCH=CHCO2H; 1,2-Ethenedicarboxylic acid, trans-[1]
ã€CAS Number】110-17-8
EINECS No. 203-743-0
ã€Molecular Structure】
InChI code: InChI=1/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+[2 ]
The simplest unsaturated dicarboxylic acid. Also known as fumaric acid or fumaric acid. It was first discovered from Corydalis, and it is also found in a variety of mushrooms and fresh beef. Fumaric acid and maleic acid are geometric isomers, and fumaric acid is heated to 250-300°C to convert to maleic acid. Fumaric acid can also produce mono- and di-esters or amides, but it cannot produce mono-acid chlorides. It reacts with phosphorous pentachloride or thionyl chloride to form a dibasic acid chloride. Fumaric acid is oxidized by potassium permanganate to produce racemic tartaric acid.
2 Physical and chemical indicators
Appearance: colorless crystals.
Melting point: 300-302°C (sealed), Sublimation at 165°C (17 mm Hg).
Melting point: 299-300°C Relative density: 1.635 (20/4°C).
Solubility: soluble in water, slightly soluble in cold water, ether, benzene, soluble in hot water, soluble in ethanol. Fumaric acid has similar chemical properties to maleic acid.
3 Preparation
There are many ways to produce fumaric acid industrially. Its main source is the oxidation of benzene (or butenes) to maleic acid (or maleic anhydride) in the presence of a catalyst, which is then isomerized. The benzene (or 80% butenes) is subjected to an oxidation reaction with excess air in a fluidized bed or fixed bed reactor to produce maleic anhydride, which is absorbed by the recycled acid into maleic acid. After decolorization and filtration, maleic acid is subjected to isomerization under the action of a thiourea catalyst. The reactants are filtered, washed, and dried to obtain fumaric acid. Isomerization catalysts also employ ammonium persulfate-ammonium bromide mixtures or metal salts, amine salts, thiols, and 10-20% hydrochloric acid. Carbohydrates such as sucrose, glucose, and maltose can also be fermented by black root bacteria to produce fumaric acid. With the method of sugar fermentation, 1t product needs 8 tons of food, which is economically uneconomical. In China, liquid paraffin was used instead of grain fermentation, and liquid wax with more C16-C18 content was used as a carbon source. After 80-88h fermentation, the liquid The conversion rate of wax is about 50%, and the extraction rate is above 50%. The furfural method uses furfural as raw material and is obtained by oxidation of sodium chlorate.
4 uses
Fumaric acid is used in the production of unsaturated polyester resins, which are characterized by good chemical resistance and heat resistance. Fumaric acid and vinyl acetate copolymers are good binders. The copolymer with styrene is a raw material for the production of glass fiber reinforced plastics. The plasticizer produced from fumaric acid is non-toxic and can be used as a vinyl acetate latex in contact with food. The product is a fine chemical intermediate such as medicine and optical bleach, used in the pharmaceutical industry for the production of the antidote dimercaptosuccinic acid, neutralization of fumaric acid with sodium carbonate, that is, sodium bromide ( [17013-01-3]), and then replaced with ferrous sulfate iron fumarate, is a drug used to treat small red blood cell anemia rich in blood iron. The product is used as a food additive - sour agent, used in refreshing beverages, fruit sugar, jelly, ice cream, etc., mostly used together with sour agent citric acid, monosodium salt made from the reaction of fumaric acid and sodium hydroxide, It is also used as a sour seasoning and also as an intermediate for synthetic resins and mordants.
5 application areas
It is mainly used in food processing of meat products and fish products. Fumaric acid can be used as an acidity regulator, an acidifier, an antioxidant aid, a pickling accelerator, and a spice. This product has a strong buffering effect, to maintain the aqueous solution at about pH 3.0, and has an important role in antibacterial and mildew. At the same time, it has astringent taste, is one of the strongest sour acid, absorption rate is low, help Extend the shelf life of powder products. When fumaric acid is converted into sodium fumarate, water solubility and flavor are better [3].
6 medical applications
According to the MD INDIA website, fumarate has been used to treat severe psoriasis. Now, researchers have found that this drug can also help prevent multiple sclerosis (MS). This study was published in the current issue of the journal of neurology Brain.
Ten years ago, Bochum, a researcher at Bochum Ruhr University (RUB), speculated that the drug may be beneficial to MS because of the TH2 polarization mechanism of fumarate.
Now, RUB's neurologists have discovered that fumarate releases free radicals in the process of scavenging inflammation, thereby protecting nerves and glial cells.
Like psoriasis, psoriasis is an autoimmune disease whose immune system attacks the body's own cells. In MS, the axon's "myelin insulating layer" is damaged in this way.
Professor Ralf Gold of Ruhr University Hospital St. Joseph's Hospital and colleagues found that the fumarate is different from the "standard drug" that resists MS. It is not only based on inhibiting or regulating the immune system, but also eliminating the release of inflammatory process. Destructive 'oxygen radicals' support the survival of nerve cells.
The transcription factor Nrf2 plays a key role in this.
"In this way, fumaric acid has a special place in MS as a neuroprotective/antioxidant," Gold said.
Under Gold's leadership, an international, placebo-controlled, blinded fumarate BG12 study incorporating 1,200 MS patients has just been completed.
The assessment is expected to take place in the summer of 2011.
"If the study is successful, it is easy to speculate that the antioxidant effect of fumaric acid is synergistically enhanced with established MS drugs such as interferon-B to form an ideal combination therapy," said Gold.
"According to the current state of knowledge, fumaric acid and interferon have no long-term risks are very important - unlike many modern and powerful MS therapeutics," he added.
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