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Fumaric acid powder, also known as fumaric acid, fumaric acid and corydric acid, CAS 110-17-8, with the chemical formula of C4H4O4, is a carboxylic acid derived from butene and is a colorless, flammable white powder or colorless crystal. It is soluble in ethanol, slightly soluble in water and ether, and insoluble in chloroform, carbon tetrachloride and benzene. Fumaric acid has a fruit sour taste, which is about 1.5 times as strong as citric acid. Therefore, low concentration fumaric acid solution can replace citric acid. However, because it is slightly soluble in water, it is generally not used alone. It is often used in combination with citric acid and tartaric acid, which can show a sour fruit taste.
Fumaric acid has a strong buffering property to maintain the pH value of the aqueous solution at about 3.0 (the pH value of the aqueous solution is 2.25-2.7), which is particularly important for preservatives and other preservatives that are suitable for functioning at about 3.0, so it is often used as one of the main components of compound preservatives. In addition, it also has weak antioxidant capacity and plays a stabilizing role in water in oil emulsifiers.
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Chemical Formula |
C4H4O4 |
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Exact Mass |
116 |
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Molecular Weight |
116 |
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m/z |
116 (100.0%), 117 (4.3%) |
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Elemental Analysis |
C, 41.39; H, 3.47; O, 55.13 |
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Fumaric acid powder, also known as fumaric acid, is an organic acid with wide application value in multiple fields. Its molecular formula is C4H4O4, which is a colorless crystal with strong acidity and astringency, as well as good water solubility. In the food industry, fumaric acid is used as an acidity regulator, acidifier, antioxidant aid, pickling promoter, and flavoring agent due to its unique physicochemical and biological properties. It plays an important role in improving the taste, shelf life, and safety of food.
1. As an acidity regulator
In the food industry, fumaric acid is commonly used as an acidity regulator to adjust the acidity and alkalinity of food, improve its taste and flavor. Its acidity is about 1.5 times that of citric acid, therefore it has a stronger sour effect. Fumaric acid can neutralize alkaline components in food, making the taste of food more acidic and refreshing, while also helping to maintain the acid-base balance of food and improve its overall quality.
(1) Application in meat products
In meat processing, fumaric acid serves as an acidity regulator, which can improve the taste and flavor of meat products. For example, in meat products such as ham sausages, sausages, and smoked sausages, fumaric acid can neutralize the alkaline components in the meat, making the meat products more delicious and tasty. At the same time, fumaric acid can also improve the water holding capacity of meat products, increase their elasticity, reduce the loss of meat juice during processing, and thus improve the yield and quality of meat products.
(2) Application in aquatic products
Fumaric acid can also act as an acidity regulator in aquatic product processing. Fumaric acid can improve the taste and flavor of aquatic products such as fish paste products, fish balls, and fish fillets, making them more delicious and tasty. In addition, fumaric acid can improve the water retention and elasticity of aquatic products, reduce water loss during processing, and thus enhance the quality and taste of aquatic products.
(3) Application in baked goods
Fumaric acid, as an acidity regulator, can improve the taste and flavor of baked goods such as bread and biscuits in baked goods. Fumaric aid can neutralize the alkaline components in flour, making baked goods softer and more delicious. Meanwhile, fumaric aid can also improve the gas holding capacity of baked goods, making them more fluffy and soft, thereby enhancing the quality and taste of baked goods.
(4) Application in beverages
Fumaric acid, as an acidity regulator, can improve the taste and flavor of beverages. For example, in refreshing drinks, fruit juice drinks, etc., fumaric acid can increase the acidity of the drink, improve its freshness and taste. At the same time, fumaric acid can also be used together with sweeteners, essence, etc. to make the taste of the beverage more diverse.
2. As an acidifier
Fumaric acid can also be used as an acidifier to lower the pH value of food, thereby inhibiting the growth and reproduction of microorganisms and extending the shelf life of food. In the food industry, fumaric acid is widely used as an acidifier.
(1) Application in fruit and vegetable products
In fruit and vegetable products, fumaric aid serves as an acidifier, which can lower the pH value of the products, thereby inhibiting the growth and reproduction of microorganisms and extending their shelf life. For example, in fruit and vegetable products such as jam, jelly, canned fruits, etc., fumaric acid can inhibit the growth of bacteria and mold, preventing the spoilage of fruit and vegetable products. Meanwhile, fumaric aid can also increase the acidity of fruit and vegetable products, improving their taste and flavor.
(2) Application in dairy products
Fumaric acid can also be used as an acidifier in dairy products. By reducing the pH value of dairy products, fumaric aid can inhibit the growth and reproduction of microorganisms such as lactic aid bacteria, thereby extending the shelf life of dairy products. In addition, fumaric aid can improve the taste and flavor of dairy products, making them more delicious and tasty.
(3) Application in soy products
Fumaric acid can also be used as an acidifier in soy products. By reducing the pH value of soy products, fumaric acid can inhibit the growth of bacteria and mold, preventing soy products from spoiling and deteriorating. Meanwhile, fumaric aid can also improve the taste and flavor of soy products, making them more delicious and tasty.
3. As an antioxidant aid
Fumaric acid has antioxidant properties, which can prevent fat oxidation and rancidity in food, thereby extending the shelf life of food. In the food industry, fumaric acid is also widely used as an antioxidant aid.
(1) Application in oil and fat products
Fumaric acid, as an antioxidant aid in oil products, can prevent oxidation and rancidity of oil, thereby extending the shelf life of oil products. For example, in edible oils, artificial butter and other oil products, fumaric aid can inhibit the oxidation and decomposition of unsaturated fatty acids in the oil, preventing the oil from producing odors and spoilage. Meanwhile, fumaric aid can also improve the stability of oil products, making them more suitable for storage and transportation.
(2) Application in meat products
Fumaric acid can also be used as an antioxidant aid in meat products. By inhibiting the oxidation and rancidity of fats in meat products, fumaric acid can extend the shelf life of meat products and prevent them from producing odors and spoilage. In addition, fumaric aid can improve the color and taste of meat products, making them more delicious and tasty.
(3) Application in baked goods
Fumaric acid, as an antioxidant aid in baked goods, can prevent the fat in baked goods from being oxidized and decomposed, thereby extending the shelf life of baked goods. For example, in baked goods such as bread and cookies, fumaric aid can inhibit the odor and spoilage caused by fat oxidation, making baked goods softer and more delicious. Meanwhile, fumaric aid can also enhance the color and taste of baked goods, making them more tempting.
4. As a pickling accelerator
Fumaric acid powder has the effect of promoting food pickling, which can accelerate the penetration and diffusion of salt in food, making food achieve pickling effect more quickly. In the food industry, fumaric aid is also widely used as a pickling accelerator.
(1) Application in pickled products
In pickled products, fumaric acid acts as a pickling accelerator, which can accelerate the penetration and diffusion of salt in pickled products, making them achieve the pickling effect more quickly. For example, in pickles, Pickled vegetables and other pickles, fumaric aid can accelerate the penetration of salt into vegetables, so that vegetables can achieve the pickling effect more quickly, and improve the quality and taste of pickles.
(2) Application in meat products
Fumaric aid can also be used as a pickling accelerator in meat products. By accelerating the penetration and diffusion of salt in meat products, fumaric aid can accelerate the pickling process, improve the quality and taste of meat products. In addition, fumaric aid can improve the color and flavor of meat products, making them more delicious and tasty.
5. As a spice
Fumaric acid itself has a unique sour taste and aroma, which can be used as a spice to enhance the taste and flavor of food. In the food industry, fumaric acid is also widely used as a flavoring agent.
(1) Application in Condiments
Fumaric acid can be used as an acidifier in seasonings to enhance their sourness and taste. For example, in seasonings such as vinegar and soy sauce, fumaric acid can increase the acidity and freshness of the seasoning, making it more suitable for cooking and seasoning.
(2) Application in Candy
In candies, fumaric aid can be used as an acidifier and flavoring agent. By increasing the acidity and aroma of candies, fumaric aid can improve their taste and flavor, making them more tempting and delicious. Meanwhile, fumaric aid can also improve the shelf life and stability of candies, preventing them from spoiling and producing unpleasant odors.
(3) Application in cold drinks
Fumaric aid can also be used as an acidifier and flavoring agent in cold drinks. By increasing the acidity and aroma of cold drinks, fumaric aid can improve their taste and flavor, making them more refreshing and delicious. Meanwhile, fumaric aid can also improve the shelf life and stability of cold drinks, preventing them from spoiling and producing unpleasant odors.
Biosynthesis:
The biosynthesis of fumaric acid powder includes enzyme catalyzed transformation and microbial fermentation. In the middle of 1990s, enzyme catalytic conversion method generally used maleic aid as substrate to prepare fumaric aid under the action of maleic aid isomerase.
This method has a high conversion efficiency and yield. If it is used together with aspartase, it can also directly prepare aspartic aid from maleic aid. Japan has done a lot of work in this regard 10-131, and studies have found that some maleic aid isomerases can withstand the high temperature of 50 ° Q, which can greatly improve the enzyme catalytic conversion efficiency. The research on fumaric aid production by mold fermentation began in the early 20th century. With the progress of science and technology, the yield of fumaric aid once reached 30%~40%.
Industrial method:
Mainly from the oxidation of benzene (or butene) to maleic aid (or maleic anhydride) in the presence of catalyst, and then through isomerization. Benzene (or 80% butene) is oxidized with excess air in a fluidized bed or fixed bed reactor to produce maleic anhydride, which is absorbed into maleic aid by circulating aid solution. After decolorization and filtration, maleic aid is isomerized with thiourea catalyst. The reactant is filtered, washed and dried to obtain fumaric aid. The isomerization catalyst also uses ammonium persulfate ammonium bromide mixture or metal salt, amine salt, mercaptan and 10-20% hydrochloric aid. Carbohydrates such as sucrose, glucose and maltose can also be fermented by Rhizopus nigrum to produce fumaric acid.
Chemical synthesis:
Process flow: benzene or butylene and air, catalytic oxidation, hydrolysis, concentration, crystallization, and finished products.
Isomerization of maleic acid
Benzene or butene (80%) and excess air are absorbed by circulating liquid field in fluidized bed or fixed bed reactor to generate maleic aid. Under the action of thiourea catalyst, maleic aid is heated to 145-260 ℃ and then isomerized to produce fumaric aid, which is then cooled, filtered, washed with hydrochloric aid, dried and crushed to obtain the finished product.
The raw materials of this method are generally prepared by benzene method and n-butane method, with a yield of about 93.0%. It has the advantages of convenient transportation, no corrosion of equipment, and low consumption. Its disadvantages are that it requires oil resources, and the process conditions are harsh.
Furfural oxidation
With furfural and water as raw materials, 58.5g KClO3 powder, an appropriate amount of V2O5/MoO3 (0.8:1) catalyst and 100mL 0.5mol/L hydrochloric acid solution were added into a 250mL beaker, stirred continuously to 110 ℃, and 20mL furfural was added dropwise. After the addition, the reaction was allowed to continue for 2h. Then, the crude fumaric aid is obtained by cooling and filtering.
The yield of this method is 83.0%. The advantages of this method are no industrial pollution, and the by-product KCl can be recycled as agricultural fertilizer. The disadvantage is that the production cost is high.
Fermentation
With liquid paraffin as raw material, Rhizopus niger as strain, the product of fumaric acid was obtained by deep fermentation for 80-90 h, followed by separation, decolorization, crystallization, drying and other multi-step processes. The conversion rate of liquid paraffin is about 50%, and the extraction rate is above 50%. In addition, it can also be fermented with raw materials such as yam and starch.
The simplest unsaturated dicarboxylic acid. Fumaric acid powder was first found in Yanhusuo, and it also exists in a variety of mushrooms and fresh beef. The fumaric acd and maleic acd are geometric isomers of each other. The fumaric acd is converted into maleic acd when heated to 250-300 ℃. The fumaric acd can also generate mono and binary esters or amides, but it cannot generate mono acyl chloride. It reacts with phosphorus pentachloride or thionyl chloride to form binary acyl chloride. The fumaric acd is oxidized by potassium permanganate to form racemic tartaric acid.
FAQ
Is fumaric acid bad for you?
Fumaric Acid can affect you when breathed in. * Contact can irritate and burn the skin and eyes. * Breathing Fumaric Acid can irritate the nose and throat causing coughing and wheezing. * Fumaric Acid may damage the kidneys.
What does fumaric acid do for skin?
PHARMACODYNAMIC EFFECTS OF FUMARIC ACID ESTERS
FAE are thought to improve psoriasis by altering leukocyte, keratinocyte, and/or endothelial functions.
Is fumaric acid allowed in Europe?
According to the harmonised classification and labelling (CLP00) approved by the European Union, this substance causes serious eye irritation. This substance is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 000 to < 100 000 tonnes per annum.
Why is fumaric acid in food?
Fumaric acid is a non-toxic, organic material used in various foods to enhance flavor, regulate acidity and lengthen shelf-life. Food types include bakery goods such as tortillas, as well as various sweets, jellies, dry mixes and powdered soft drinks.
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