Fumaric acid

Fumaric acid is an organic compound with the chemical formula C₄H₄O₄. It is widely used in industrial production, food processing, pharmaceuticals, and agriculture. Its core functions revolve around three key aspects: "acid regulation," "chemical reaction carrier," and "physiological activity." Its specific roles vary significantly across different fields. Below is a detailed classification:

I. Industrial Field: As a Basic Chemical Raw Material

In industry, fumaric acid is primarily utilized for its acidity, stability, and chemical reactivity. It is used to produce downstream chemical products and serves as a key intermediate in industries such as polymer materials and coatings.

1. Synthesis of Polymer Materials
   Its most critical application is copolymerization with other monomers (such as ethylene and propylene) to produce unsaturated polyester resin (UPR). This type of resin exhibits high strength and corrosion resistance, making it widely used in the manufacturing of fiberglass (for ships, pipelines, and recreational facilities), artificial marble, and electrical insulation components. Additionally, fumaric acid can be used to synthesize "dimethyl fumarate (DMF)" (Note: DMF was once used as an antifungal agent but has been restricted in some countries for applications in food packaging and furniture due to skin irritation).
2. Coatings and Adhesives
   As a "crosslinking agent" or "curing agent" in coatings, it enhances adhesion and weather resistance (e.g., anti-corrosion coatings for outdoor use). Adding fumaric acid to adhesives improves bonding strength and water resistance.
3. Water Treatment Agent
   Its acidity helps adjust the pH of industrial wastewater, while it also binds with calcium and magnesium ions in water to assist in softening water quality and reducing pipeline scaling (often used in combination with other chelating agents).

II. Food Field: As a Food Additive (Acidity Regulator, Antioxidant)

In the food industry, fumaric acid is classified as a legal food additive (permitted under China's GB 2760 standard). Its safety has been evaluated by the Food and Agriculture Organization (FAO) and the World Health Organization (WHO). Its primary functions include:

1. Acidity Regulation and Flavor Enhancement
   Fumaric acid has higher acidity (pKa≈3.03) than citric acid and malic acid, with a lasting sour taste and no off-flavors. It provides a refreshing sourness to foods and is commonly used in:
   • Beverages (carbonated drinks, fruit juices): Adjusts pH, enhances taste complexity, and inhibits microbial growth (low pH environments delay spoilage);
   • Jellies, jams, and preserves: Partially replaces citric acid, reduces excessive sweetness, and improves product stability (prevents sugar crystallization);
   • Baked goods (bread, biscuits): Acts as an "acidulant" to adjust dough pH, improve yeast fermentation efficiency, and result in softer products.
2. Antioxidant and Color Preservation
   Fumaric acid inhibits the activity of "polyphenol oxidase" in food, reducing browning in processed fruits and vegetables (e.g., canned goods, dried fruits). It also chelates metal ions (such as iron and copper), preventing them from catalyzing lipid oxidation and extending food shelf life (often used in combination with vitamin E, tea polyphenols, etc.).
3. Feed Additive
   Adding small amounts of fumaric acid to livestock and poultry feed helps regulate intestinal pH (reducing alkaline conditions), inhibits the growth of harmful bacteria (e.g., E. coli), and promotes nutrient absorption (particularly improving the utilization of calcium and phosphorus). It is commonly used in feed for piglets and chicks.

III. Pharmaceutical Field: As a Drug Ingredient or Intermediate

In pharmaceuticals, fumaric acid has two main applications: as an active pharmaceutical ingredient for treating specific diseases and as a pharmaceutical excipient to improve drug properties.

1. Treatment of Autoimmune Diseases: Fumarate Drugs
   Clinically, derivatives such as "dimethyl fumarate (DMF)" and "monomethyl fumarate" are commonly used rather than pure fumaric acid. Their mechanism of action involves modulating immune cells (e.g., inhibiting excessive T-cell activation and reducing inflammatory cytokine release). They are used to treat:
   • Multiple Sclerosis (MS): One of the first oral treatments for relapsing-remitting MS globally (e.g., brand name Tecfidera), which reduces relapse rates and delays neurological damage;
   • Psoriasis: Topical or oral fumarate drugs can inhibit abnormal proliferation of skin keratinocytes, reducing symptoms like redness and scaling (must be used under medical supervision to avoid side effects).
2. As a Pharmaceutical Excipient
   • Utilizing its acidity, it serves as a component in "effervescent tablet disintegrants" (reacting with sodium bicarbonate to produce carbon dioxide, enabling rapid tablet disintegration in water);
   • Improving drug solubility: Some alkaline drugs (e.g., certain antibiotics) form salts with fumaric acid (e.g., azithromycin fumarate), enhancing their solubility in water and promoting absorption in the body.

IV. Other Fields

• Agriculture: As a "plant growth regulator," low concentrations of fumaric acid can promote root development and enhance stress resistance (e.g., drought and salt tolerance). It is also used as an "herbicide intermediate" to synthesize selective herbicides (e.g., agents for controlling weeds in wheat fields).
• Cosmetics: Used in small amounts in skincare products to adjust pH or stabilize other active ingredients (e.g., vitamin C), preventing product deterioration.