The main difference between fumarate and hemifumarate is that fumarate is a dicarboxylic acid and has two carboxylic acid functional groups in its chemical structure, whereas hemifumarate is a derivative of fumarate but contains only one carboxylic acid functional group.
Fumarate and hemifumarate are two compounds that contain carboxylic acid functional groups (-COOH) in their structures.
Key Areas Covered
1. What is Fumarate
– Definition, Features
2. What is Hemifumarate
– Definition, Features
3. Similarities Between Fumarate and Hemifumarate
– Outline of Common Features
4. Difference Between Fumarate and Hemifumarate
– Comparison of Key Differences
Key Terms
2-Butenedioic Acid, C4H4O3, C4H4O4, Fumarate, Hemifumarate
What is Fumarate
Fumarate is a dicarboxylic acid, which means it contains two carboxylic acid (-COOH) functional groups in its chemical structure. The molecular formula of fumarate is C4H4O4. Its chemical structure consists of a carbon-carbon double bond between two of its carbon atoms, with carboxylic acid groups attached to adjacent carbon atoms. Fumarate exists as a geometric isomer, specifically the trans-isomer, where the two carboxylic acid groups are positioned on opposite sides of the double bond. This trans configuration gives fumarate its distinct structure and properties. One notable property of fumarate is its solubility in water. It readily dissolves in water to form a mildly acidic solution, which can participate in various chemical reactions and biochemical processes.
Applications of Fumarate
Fumarate salts are commonly used in the pharmaceutical industry. These salts are formed by combining fumaric acid with various bases, resulting in compounds where fumarate acts as a counterion. Fumarate salts help to improve the stability, solubility, and bioavailability of certain drugs. For example, quetiapine fumarate is a common medication for psychiatric conditions. Fumarate salts are useful in the development of controlled-release drug formulations, allowing for extended drug delivery and improved patient compliance. Some chemotherapy drugs are formulated as fumarate salts to enhance their effectiveness and tolerability. Fumaric acid esters (FAEs), derived from fumaric acid, are used in the treatment of psoriasis, a chronic skin condition. FAEs can modulate the immune response and reduce inflammation.
Figure 1: Quetiapine Fumarate
Meanwhile, fumaric acid is used as an acidulant in the food and beverage industry. It contributes to the tartness of certain foods and serves as an alternative to other acids like citric acid. Fumarate-based compounds are useful in the production of certain polymers and resins. They can enhance the properties of these materials, such as their resistance to heat and chemicals. Fumaric acid and its salts are sometimes added to animal feed to improve digestion and nutrient absorption in livestock.
What is Hemifumarate
Hemifumarate, also known as 2-butenedioic acid, is a dicarboxylic acid with the molecular formula C4H4O3. Hemifumarate is formed when fumarate is hydrated to malate by the enzyme fumarase during the citric acid cycle. Unlike fumarate, hemifumarate has one carboxyl (-COOH) group and one hydroxyl (-OH) group in its structure. It serves as an intermediate compound in the conversion of fumarate to malate, contributing to energy production within cells.
One of the most notable properties of hemifumarate is its geometric isomerism. It exists in two geometric isomeric forms: cis-hemifumarate and trans-hemifumarate, which differ in the spatial orientation of the carboxylic acid groups. The cis-isomer has the carboxylic acid groups on the same side of the double bond, while the trans-isomer has them on opposite sides. This isomerism has significant implications for its chemical and biological activities.
Hemifumarate is a lesser-known compound with significant roles in medicine, biology, and the pharmaceutical industry. In the tricarboxylic acid cycle, it serves as an intermediate metabolite, crucial for energy production. Hemifumarate and its isomers are of interest in medicine due to their potential therapeutic effects, such as anti-inflammatory and antioxidant properties. While some studies explore their use in disease treatment, more research is needed for a comprehensive understanding. Changes in hemifumarate levels are linked to diseases like cancer and metabolic disorders, offering insights into disease mechanisms. Additionally, hemifumarate finds practical application in the pharmaceutical industry, enhancing drug stability, solubility, and bioavailability when used as a salt form in certain formulations. The choice of hemifumarate as a salt form depends on the specific drug properties required for formulation.
Similarities Between Fumerate and Hemifumarate
- Both fumarate and hemifumarate are found in living organisms and play roles in cellular metabolism.
- These compounds contain carboxylic acid functional groups (-COOH) in their structures.
Difference Between Fumerate and Hemifumarate
Definition
Fumarate is the salt or ester of fumaric acid, a dicarboxylic acid commonly involved in biological and chemical processes, whereas hemifumarate is an intermediate in the conversion of fumarate to malate by the enzyme fumarase.
Molecular Formula
The molecular formula of fumarate is C4H4O4 while the molecular formula of hemifumarate is C4H4O3.
Carboxylic Acid
Fumarate is a dicarboxylic acid, containing two carboxylic acid functional groups, whereas hemifumarate contains only one carboxylic acid functional group.
Biological Significance
Fumarate is a well-established and essential compound in cellular metabolism, while hemifumarate is less well-known and has received less attention in the context of cellular metabolism.
Conclusion
The main difference between fumarate and hemifumarate is that fumarate is a dicarboxylic acid and has two carboxylic acid functional groups in its chemical structure, whereas hemifumarate is a derivative of fumarate but contains only one carboxylic acid functional group.
Reference:
1. “Fumarate: Multiple functions of a simple metabolite.” Science Direct.
2. “Hemifumarate.” Wiktionary, the Free Dictionary.
Image Courtesy:
1. “Quetiapine Fumarate 50mg tablets” By INeverCry – Own work (CC0) via Commons Wikimedia
Leave a Reply