Fumaric acid is a naturally occurring organic acid found in fruits and vegetables. It is used as a food additive, pH regulator, and ingredient in various industries, including pharmaceuticals and cosmetics.
| IUPAC Name | (E)-Butenedioic acid |
| Molecular Formula | C4H4O4 |
| CAS Number | 110-17-8 |
| Synonyms | Trans-butenedioic acid, Allomaleic acid, 2-butenedioic acid |
| InChI | InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8) |
Fumaric Acid Properties
Fumaric Acid Formula
The formula of fumaric acid or 2-butenedioic acid is C4H4O4. It consists of four carbon atoms, four hydrogen atoms, and four oxygen atoms. The formula represents the structural arrangement of these atoms in the molecule of fumaric acid.
Fumaric Acid Molar Mass
The molar mass of 2-butenedioic acid is calculated by adding up the atomic masses of its constituent elements. With four carbon atoms, four hydrogen atoms, and four oxygen atoms, the molar mass of 2-butenedioic acid is approximately 116.07 grams per mole.
Fumaric Acid Boiling Point
2-butenedioic acid has a boiling point of around 287 degrees Celsius. This is the temperature at which the liquid form of 2-butenedioic acid converts into a gas phase under standard atmospheric pressure.
Fumaric Acid Melting Point
2-butenedioic acid has a melting point of about 287-298 degrees Celsius. This is the temperature range at which the solid form of 2-butenedioic acid transforms into a liquid state.
Fumaric Acid Density g/mL
The density of 2-butenedioic acid is approximately 1.635 grams per milliliter. Density represents the mass of a substance per unit volume and is commonly measured in grams per milliliter for liquids or solids.
Fumaric Acid Molecular Weight
The molecular weight of 2-butenedioic acid is approximately 116.07 grams per mole. It is calculated by summing up the atomic weights of all the atoms in a single molecule of 2-butenedioic acid.
Fumaric Acid Structure
The structure of 2-butenedioic acid consists of two carboxylic acid groups (COOH) attached to a central carbon-carbon double bond. This arrangement gives 2-butenedioic acid a trans configuration, which is responsible for its unique chemical and physical properties.
Fumaric Acid Solubility
2-butenedioic acid is sparingly soluble in water, meaning it has limited ability to dissolve in an aqueous solution. However, it is more soluble in organic solvents such as ethanol and acetone. The solubility of 2-butenedioic acid varies depending on the temperature and the solvent used.
| Appearance | White crystalline powder |
| Specific Gravity | 1.635 g/mL |
| Color | Colorless |
| Odor | Odorless |
| Molar Mass | 116.07 g/mol |
| Density | 1.635 g/mL |
| Melting Point | 287-298 °C |
| Boiling Point | 287 °C |
| Flash Point | Not applicable |
| Water Solubility | Slightly soluble |
| Solubility | Soluble in organic solvents such as ethanol and acetone |
| Vapor Pressure | Negligible |
| Vapor Density | Not available |
| pKa | 3.03 (at 25 °C) |
| pH | Approximately 2-3 |
Fumaric Acid Safety and Hazards
2-butenedioic acid poses minimal safety hazards when handled properly. It is considered non-toxic and has a low potential for causing harm. However, it may cause mild irritation to the skin, eyes, and respiratory system if exposed in high concentrations. It is advisable to wear appropriate protective equipment such as gloves and goggles when working with 2-butenedioic acid. In case of accidental ingestion, immediate medical attention should be sought. It is important to store 2-butenedioic acid in a cool, dry place away from incompatible substances. Overall, with proper handling and adherence to safety precautions, 2-butenedioic acid can be used safely in various industries.
| Hazard Symbols | None |
| Safety Description | Low toxicity. Proper handling and precautions recommended. |
| UN IDs | Not applicable |
| HS Code | 2917.19.90 |
| Hazard Class | Not classified |
| Packing Group | Not classified |
| Toxicity | Low toxicity |
Fumaric Acid Synthesis Methods
Various methods can synthesize 2-butenedioic acid.
One common method is the catalytic isomerization of maleic acid. This process involves the use of a catalyst, such as iodine or palladium, to convert maleic acid into 2-butenedioic acid. The reaction occurs under specific conditions of temperature and pressure.
Another method involves the oxidation of furfural, a compound derived from biomass. Furfural undergoes oxidation in the presence of an oxidizing agent, such as nitric acid or hydrogen peroxide, to yield 2-butenedioic acid.
Certain microorganisms can produce 2-butenedioic acid through fermentation. For instance, certain strains of Rhizopus or Aspergillus fungi can convert glucose or other sugars into 2-butenedioic acid through a metabolic pathway.
Natural sources, such as apples and grapes, yield 2-butenedioic acid, which can be extracted and purified for commercial use.
Overall, these synthesis methods offer different approaches to obtaining 2-butenedioic acid. The choice of method depends on factors such as availability of starting materials, efficiency, and environmental considerations.
Fumaric Acid Uses
2-butene-dioic acid has diverse applications across various industries due to its unique properties. Here are some of its common uses:
- Food Industry: The food and beverage industry utilizes 2-butenedioic acid actively as an acidulant and flavor enhancer. Manufacturers add it to carbonated drinks, fruit juices, candies, and gelatin desserts to impart tartness and enhance flavor.
- Pharmaceutical Industry: The pharmaceutical industry actively employs 2-butenedioic acid in the production of medications, particularly those used for treating certain skin conditions like psoriasis. It serves as a key ingredient in formulating oral medications and dietary supplements.
- Cosmetics and Personal Care: 2-butenedioic acid actively finds its place in cosmetics and personal care products. Skincare formulations, such as creams and lotions, use it to actively enhance stability, adjust pH levels, and act as a preservative.
- Industrial Applications: Various industrial applications actively rely on 2-butenedioic acid as a crucial component. The production of resins, polymers, and plastics actively utilizes it, including its use in unsaturated polyester resins for fiberglass-reinforced composites.
- Animal Feed: 2-butenedioic acid actively serves as a feed acidifier when added to animal feed. It actively improves digestion and nutrient absorption in livestock, actively promoting animal health and growth.
- Cleaning Products: Cleaning product manufacturers actively use 2-butenedioic acid as a pH regulator and chelating agent. It actively maintains desired pH levels and enhances the cleaning efficiency of detergents.
- Other Uses: 2-butenedioic acid finds active applications in the production of adhesives, textiles, and printing inks. It actively plays a role in water treatment processes for actively controlling pH levels.
These diverse applications highlight the versatility of 2-butenedioic acid and its significance in multiple industries.
Questions:
Q: What is fumaric acid?
A: 2-butenedioic acid is a naturally occurring organic acid found in fruits and vegetables, used as a food additive and in various industries.
Q: Is maleic acid or fumaric acid more reactive with bromine?
A: Maleic acid is more reactive with bromine compared to 2-butenedioic acid due to its cis configuration.
Q: Is fumaric acid bad for you?
A: 2-butenedioic acid is generally considered safe for consumption in moderate amounts and is approved as a food additive by regulatory authorities.
Q: How much fumaric acid will dissolve in 100 ml of acetone?
A: The solubility of 2-butenedioic acid in acetone varies, but approximately 5-10 grams may dissolve in 100 ml of acetone.
Q: What is fumaric acid in food?
A: 2-butenedioic acid is used as a food additive in various products to provide tartness, enhance flavors, and regulate acidity levels.
Q: What happens when fumaric acid is mixed with sodium bicarbonate?
A: When 2-butenedioic acid is mixed with sodium bicarbonate, a reaction occurs, releasing carbon dioxide gas, water, and forming sodium fumarate.
Q: Is fumaric acid water?
A: No, 2-butenedioic acid is not water itself but a type of organic acid that can dissolve in water.
Q: What is fumaric acid made from?
A: 2-butenedioic acid can be synthesized from maleic acid through isomerization or obtained from natural sources like fruits and vegetables.
Q: What turns free amino acids into pyruvate and fumarate?
A: The process of oxidative decarboxylation converts free amino acids into pyruvate and fumarate in certain metabolic pathways.
Q: How does fumaric acid (E 297) regulate acidity?
A: Fumaric acid (E 297) acts as an acidulant and pH regulator, contributing to the regulation of acidity in food and beverage products.