Fumaric Acid Formula: Structure, Properties, Uses, Health Hazards

Fumaric acid , an organic compound of carbon, is identified by the chemical formula C ₄ H ₄ O ₄ . Primarily in solid form, this white-colored substance has a fruit-like taste and is called Allomaleic acid. As a dicarboxylic acid, it is commonly used as a food additive and can even be naturally produced by human skin when exposed to sunlight. In fact, fumaric acid is a by-product of the urea cycle in humans. Its salts and esters are collectively known as fumarates. It was first discovered in 1817 by Braconnet and Vauquelin during their experiments on malic acid distillation and maleic acid.

What is Fumaric Acid?

In addition to its common name, Fumaric Acid is also referred to as Allomaleic Acid or Turmeric Acid. It serves as a precursor to L-malate in the TCA cycle, also known as the Krebs Cycle. The production of Fumaric Acid involves oxidizing succinic acid through the use of succinate dehydrogenase. This reaction converts fumarate to malate with the help of the fumarate enzyme. Interestingly, high concentrations of Fumaric Acid can be found in bio-fluids surrounding tumors or within human tumors themselves. Given its properties, Fumaric Acid is expected to enhance the quality of various food and beverage products.

Preparation Method of Fumaric Acid

• The isomerization of maleic acid produces fumaric acid. In this reaction catalyst such as mineral, and acid is used.
• Dilute Bromo succinic acid heated with KOH can produce fumaric acid.
• Fumaric acid can be prepared by reduction of tartaric acid in presence of phosphorus and iodine.
• Bromosuccinic acid and water can be heated to produce fumaric acid.
• The preparation of fumaric acid can be accomplished by heating Maleic acid above 2000 degrees Celsius.

Structure of Fumaric Acid

The chemical formula for fumaric acid is C ₄ H ₄ O _4, and it is usually found in its solid form and is white in color. It is also known as Allomaleic acid. A dicarboxylic acid, Fumaric acid has the IUPAC name (E)-Butenedioic acid. It is the trans-isomer of butenedioic acid. With its carbon-carbon double bond, Fumaric acid has a molecular shape of E. It has a molecular weight of 116 amu.

Properties of Fumaric Acid Formula

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Physical Properties of Fumaric Acid

• It mostly appears as a white-colored solid.
• It has a fruit-like odor.
• Fumaric acid is Combustible but it is difficult to start a fire.
• Fumaric acid undergoes sublimation at 200 C. Fumaric acid melts at 572-576 °F.

Chemical Properties of Fumaric Acid

• There is little capacity for Fumaric acid to absorb atmospheric moisture.
• It is soluble in alcohol but insoluble in benzene, water, or chloroform.
• When Fumaric acid is heated in the presence of Bayers reagent, Racemic Tartaric Acid is formed.
• The pH of Fumaric acid is 3.19.
• 2,3-dibromosuccinic acid is formed by bromination of fumaric acid.
• DL-malic acid is produced by heating fumaric acid in a closed vessel with water at almost 150 - 170 °C.
• Dimethyl fumarate is formed when fumaric acid and methanol are heated in the presence of sulfuric acid.

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Uses of Fumaric Acid

• In addition to treating psoriasis, fumaric acid esters are used as a food additive due to their antioxidant and anti-inflammatory properties.
• Because of the low water absorption capacity of fumaric acid, it helps preserve the flavor and quality of food products.
• Pharmacies use fumaric acid to manufacture ferrous fumarate and alexipharmic.
• Tartaric acid is produced from fumaric acid.

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Health Hazards of Fumaric Acid

• When Fumaric acid comes in direct contact with the eyes it causes irritation.
• Inhaling of Fumaric acid can cause irritation in the nose and throat which leads to coughing.
• Exposure to Fumaric acid for a long period of time can lead to kidney damage.