Fumaric acid
[CAS# 110-17-8]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Acyclic carboxylic acid
• Name: Fumaric acid
• Synonyms: (E)-2-Butenedioic acid; Butenedioic acid; (E)-1,2-Ethenedicarboxylic acid; TMEDA
• Molecular Formula: C₄H₄O₄
• Molecular Weight: 116.07
• CAS Registry Number: 110-17-8
• EC Number: 203-743-0
• FEMA: 2488
• SMILES: C(=C/C(=O)O)C(=O)O

Properties

• Density: 1.625
• Melting point: 295-300 °C
• Flash point: 230 °C
• Water solubility: 0.63 g/100 mL (25 °C)

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H290-H314-H318-H319
• Safety Statements: P234-P260-P264-P264+P265-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P317-P321-P337+P317-P363-P390-P405-P406-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H332
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

• Transport Information: UN 9126

Discovery and Applications

Fumaric acid, a naturally occurring dicarboxylic acid, was first discovered in the early 19th century by the French chemist L. F. B. Malic acid, its isomer, was initially thought to be responsible for the sour taste of apples. However, in 1832, the German chemist Leopold Gmelin isolated fumaric acid from common table salt, providing crucial insights into its chemical properties and distinct structure. This discovery laid the foundation for further research into fumaric acid's properties and applications in various industries.

Fumaric acid serves as a widely used food additive, primarily as an acidulant and flavor enhancer. It is approved by regulatory agencies worldwide for use in food and beverage products. Fumaric acid is utilized in sour candies, gelatin desserts, fruit-flavored beverages, and bakery products to impart tartness and enhance flavor. Its acidity also contributes to food preservation by inhibiting the growth of bacteria and fungi, extending shelf life.

Fumaric acid derivatives, such as dimethyl fumarate (DMF), are employed in pharmaceuticals for the treatment of various medical conditions. DMF, approved for the treatment of multiple sclerosis, exhibits immunomodulatory and anti-inflammatory effects. It is also investigated for its potential therapeutic applications in psoriasis and other autoimmune diseases. Fumaric acid's role in pharmaceuticals underscores its importance in improving human health and well-being.

Fumaric acid finds applications in various industrial processes, including the production of resins, polymers, and alkyd resins. It is used as a precursor in the synthesis of unsaturated polyester resins, which are employed in composite materials, coatings, and adhesives. Fumaric acid-based resins offer excellent mechanical properties, chemical resistance, and weatherability, making them suitable for diverse industrial applications.

Fumaric acid is utilized in the beverage industry as an acidulant and pH regulator. It is added to carbonated beverages, fruit juices, and energy drinks to impart tartness and acidity. Fumaric acid enhances the flavor profile of beverages while providing stability and improving product quality. Its use in beverages extends to both non-alcoholic and alcoholic drinks, contributing to their sensory attributes and consumer acceptance.

Fumaric acid is included in animal feed formulations to improve digestibility and nutrient absorption in livestock and poultry. It acts as a feed acidifier, lowering the pH of the digestive tract and creating favorable conditions for beneficial gut microflora. By optimizing digestion and nutrient utilization, fumaric acid enhances animal health, growth performance, and feed efficiency. Its use in animal feed contributes to sustainable livestock production and welfare.

References

1979. Transport of malate and citrate into rat brain mitochondria under hypoxia and anesthesia. Neurochemical Research.
DOI: 10.1007/bf00963805

2013. Fumaric Acid Microenvironment Tablet Formulation and Process Development for Crystalline Cenicriviroc Mesylate, a BCS IV Compound. Molecular Pharmaceutics.
DOI: 10.1021/mp400286s

2015. Direct fungal fermentation of lignocellulosic biomass into itaconic, fumaric, and malic acids: current and future prospects. Journal of Industrial Microbiology and Biotechnology.
DOI: 10.1007/s10295-014-1575-4