Isabella Carter
Dimethyl maleate and dimethyl fumarate are both compounds with a range of applications. Dimethyl fumarate (DMF) is used in medicine as a treatment for psoriasis and multiple sclerosis. It is also used as a biocide in furniture and shoes to prevent mould growth. Dimethyl maleate, on the other hand, is a compound that undergoes isomerization into its trans counterpart when catalyzed by certain palladium(0) olefin complexes. This raises the question: are these two compounds constitutional isomers?
| Characteristics | Values |
|---|---|
| Dimethyl Maleate | A compound that undergoes isomerization into its trans counterpart |
| Dimethyl Fumarate | The methyl ester of fumaric acid |
| Reaction | Dimethyl Maleate + CCl3CO2Na → Dihydroindolizines |
| Dimethyl Fumarate + CCl3CO2Na → Dihydroindolizines |
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What You'll Learn
- Dimethyl fumarate is the methyl ester of fumaric acid
- Dimethyl fumarate is used to treat multiple sclerosis
- Dimethyl maleate undergoes isomerization into its trans counterpart
- Dimethyl maleate selectively inserts into cobaltcyclobutene complex
- Dimethyl fumarate is used as a biocide in furniture and shoes
Dimethyl fumarate is the methyl ester of fumaric acid
Dimethyl fumarate (DMF) is the methyl ester of fumaric acid. It is named after the earth smoke plant (Fumaria officinalis). Dimethyl fumarate is an old compound that has been used in industrial chemistry and can be purchased by the ton. It is also available as a generic medication.
Dimethyl fumarate has been used as a biocide in furniture or shoes to prevent the growth of moulds during storage or transport in humid climates. In Germany, it is marketed for the treatment of psoriasis and is available as an oral formulation mixed with related compounds (Fumaderm). The Swiss company Fumapharm brought Fumaderm, an oral formulation of dimethyl fumarate, to market for psoriasis in Germany in 1994. It is also available in the US as an oral formulation (Tecfidera) to treat adults with relapsing multiple sclerosis.
The precise mechanism of action of dimethyl fumarate is not clear. However, it is believed to possess immunomodulatory properties without causing significant immunosuppression. For psoriasis, the mechanism of action is believed to be due to the interaction of monomethyl fumarate and the intracellular reduced glutathione of cells directly involved in the pathogenesis of psoriasis. Dimethyl fumarate can also activate the transcription factor (Nuclear factor erythroid-derived 2)-related factor 2 (Nrf2) pathway.
Initial clinical research on the use of dimethyl fumarate for the treatment of multiple sclerosis was conducted by Fumapharm in collaboration with Biogen Idec. Biogen continued developing its oral formulation of dimethyl fumarate from Fumapharm under the code name BG-12. It was approved under the trade name Tecfidera for the treatment of adults with relapsing forms of MS in 2013.
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Dimethyl fumarate is used to treat multiple sclerosis
Dimethyl fumarate (DMF) is the methyl ester of fumaric acid and is named after the earth smoke plant (*Fumaria officinalis*). It is available as a generic medication and is also marketed under the brand name Tecfidera. Dimethyl fumarate is a disease-modifying therapy (DMT) for relapsing multiple sclerosis (MS). It is taken as a tablet, usually twice daily.
The use of dimethyl fumarate for the treatment of multiple sclerosis was initially investigated by the Swiss company Fumapharm in collaboration with Biogen Idec. Fumapharm brought an oral formulation of dimethyl fumarate (along with some monoesters) to market for psoriasis in Germany in 1994. Based on the efficacy and safety of this formulation, an oral formulation of dimethyl fumarate was subsequently developed by Almirall and approved by the European Medicines Agency (EMA) in 2017 for the treatment of moderate-to-severe plaque psoriasis in adults.
In 2013, dimethyl fumarate was approved by the U.S. Food and Drug Administration (FDA) as a treatment option for adults with relapsing multiple sclerosis. It has also been approved for this use in Europe. A 2015 Cochrane systematic review found moderate-quality evidence of a reduction in relapses over a two-year treatment period with dimethyl fumarate compared to a placebo. The review also found low-quality evidence of a reduction in worsening disability, but overall, higher-quality studies with longer follow-up are needed.
The effectiveness of dimethyl fumarate for relapsing multiple sclerosis is classed as "good", between DMTs classed as "high" effectiveness and those classed as "moderate". On average, people taking dimethyl fumarate experienced a 53% drop in the number of relapses compared to those taking a placebo. Additionally, there was a 38% drop in the risk of their disability getting worse compared to those on a placebo. Dimethyl fumarate is thought to have immunomodulatory properties without causing significant immunosuppression. It impairs differentiated B cells and fosters central nervous system integrity in the treatment of multiple sclerosis.
However, there are some important considerations and potential side effects associated with dimethyl fumarate. It is not licensed to be used during pregnancy, although there is no evidence that it harms babies in the womb. It is recommended that women who can get pregnant use reliable contraception while taking dimethyl fumarate and that they discuss the benefits and risks of taking it while pregnant with their neurologist. Additionally, stomach problems are a common side effect of the drug, especially early on. Blood tests before and during treatment are also necessary as it may affect the kidneys, liver, and white blood cell count. Dimethyl fumarate can also increase the chances of developing a rare viral brain infection called PML (progressive multifocal leukoencephalopathy).
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Dimethyl maleate undergoes isomerization into its trans counterpart
Dimethyl maleate (DMM) can undergo isomerization into its trans counterpart, dimethyl fumarate (DMF), through a reaction mechanism known as the aza-Michael addition. This process involves the addition of an amine to an electron-deficient C=C double bond, specifically the conversion of maleate esters to fumarate esters. The aza-Michael reaction is a versatile tool for modifying α,β-unsaturated carbonyl compounds, and its kinetics and mechanism have been studied in detail.
The isomerization of dimethyl maleate to dimethyl fumarate was investigated by Karaman and colleagues, who proposed a reaction mechanism based on their DFT mechanistic study. They suggested that the cis-to-trans isomerization occurs through a reaction intermediate, specifically the formation of an aza-Michael adduct with another amine molecule bonded by a hydrogen bond to its carbonyl group. This study provides valuable insights into the isomerization process, helping to understand the structural transformations involved.
The isomerization of dimethyl maleate has been observed in various experimental contexts. For example, when treated with a 1:1 mixture of cis- and trans-CFClCFCl, bis(cyclooctadiene) platinum(0) forms the corresponding fumarate complexes. Similarly, when reacted with cobaltcyclobutene complex 68, dimethyl maleate yields the 69-ZZ cobalt-diene complex, which, upon heating, undergoes thermal conversion to the 69-ZE complex, reaching equilibrium after 116 hours at 70°C. These reactions provide further evidence of the isomerization of dimethyl maleate to its trans counterpart, dimethyl fumarate.
Additionally, the isomerization of dimethyl maleate has been explored in the context of regioselectivity. The reaction of ethyl-Z-β-cyanoacrylate with cobaltcyclobutene complex 68 yielded the crystalline product 71-ZE, indicating a selective transformation. Furthermore, the reaction of 2-methyl-2-nitrosopropane with the cobaltcyclobutene complex led to the formation of a single isomer, the cobalt(III)-η2(N,O)-hydroxylamido complex. These experiments contribute to our understanding of the isomerization process and its selectivity.
In summary, dimethyl maleate undergoes isomerization into its trans counterpart, dimethyl fumarate, through the aza-Michael addition of amines. This process has been studied computationally and experimentally, providing insights into the reaction mechanism and its applications in organic synthesis. The isomerization of dimethyl maleate offers a versatile tool for synthesizing fumarate esters and exploring regioselective transformations.
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Dimethyl maleate selectively inserts into cobaltcyclobutene complex
Dimethyl maleate and dimethyl fumarate are not constitutional isomers. Dimethyl maleate is a compound that selectively inserts into the cobaltcyclobutene complex. This insertion results in the formation of an air-stable cobalt-diene complex. The cobaltcyclobutene complex is prepared by condensing cyclobutene with an iridium complex at low temperatures and then warming it to room temperature. The reaction of dimethyl maleate with cobaltcyclobutene involves the replacement of triphenylphosphine by dimethyl maleate, leading to the formation of a cyclohexadiene complex.
Dimethyl maleate undergoes isomerization when catalyzed by certain palladium(0) olefin complexes due to the presence of electron-withdrawing conjugated systems. This isomerization results in the formation of its trans counterpart. Additionally, dimethyl maleate's reaction with specific iridium(I) complexes produces adducts with distinct structural characteristics. For instance, reacting dimethyl maleate with trans-Ir(CO)(Me)(PPh3)2 yields a trigonal-bipyramidal adduct.
The Diels-Alder reaction of cyclopentadiene with dimethyl maleate can lead to both exo and endo products. However, the specific conditions and mechanisms governing the formation of these products require further investigation. Dimethyl maleate's selective insertion into the cobaltcyclobutene complex is an example of its reactivity with transition metal complexes, showcasing its ability to form stable compounds with specific geometric configurations.
In the realm of medicine and biochemistry, dimethyl fumarate (DMF) has garnered attention for its therapeutic applications. Dimethyl fumarate is the methyl ester of fumaric acid and has been utilized in oral therapies for psoriasis and multiple sclerosis. Its use in treating these conditions has been approved in various regions, including Germany, the United States, and the European Union. Dimethyl fumarate is also employed as a biocide in products such as furniture and shoes to prevent mold growth during storage or transport in humid climates.
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Dimethyl fumarate is used as a biocide in furniture and shoes
Dimethyl fumarate (DMF) is a biocide used to prevent mould growth in leather products, such as shoes and furniture, during storage or transportation in humid climates. However, due to cases of allergic reactions and severe skin reactions, dimethyl fumarate-containing consumer products are no longer authorised for manufacture or import in the European Union. The Risk Assessment Committee supported a proposal to implement a permanent ban on DMF due to the serious health risk it poses to consumers.
Dimethyl fumarate is also known as the methyl ester of fumaric acid and is named after the earth smoke plant (Fumaria officinalis). It is metabolised into monomethyl fumarate (MMF) before entering systemic distribution. The precise mechanism of action of dimethyl fumarate is unclear, but it is believed to have immunomodulatory properties. Dimethyl fumarate and MMF can activate the Nrf2 pathway, and MMF has been identified as a nicotinic acid receptor agonist in vitro. Additionally, dimethyl fumarate can reduce the expression of micro-RNA-21, which is essential for the production of pathogenic cells in multiple sclerosis and psoriasis.
In the context of medical applications, dimethyl fumarate has been used as a treatment for moderate-to-severe plaque psoriasis and relapsing forms of multiple sclerosis (MS). It is available as an oral formulation under brand names such as Skilarence, Tecfidera, and Fumaderm. The first medical use of fumaric acid, a topical formulation for psoriasis, was described by German chemist Walter Schweckendiek in 1959. Since then, oral formulations have been developed and approved for use in various regions, including the United States, Europe, and the United Kingdom.
It is important to note that dimethyl fumarate should not be confused with dimethyl maleate, which is a separate compound. Dimethyl maleate undergoes isomerization to form dimethyl fumarate under specific reaction conditions. Dimethyl maleate is also involved in various chemical reactions, such as those with cobaltcyclobutene complexes and pyridines, leading to the formation of different complexes and compounds.
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Frequently asked questions
Dimethyl Maleate is a compound that undergoes isomerization into its trans counterpart.
Dimethyl fumarate (DMF) is the methyl ester of fumaric acid.
Yes, dimethyl maleate and dimethyl fumarate are constitutional isomers.
In a study, 1,3,4-Triphenyl-1,2-dihydrophosphite reacted with dimethyl maleate to produce a mixture of diastereomeric cycloadducts, which indicated that dimethyl maleate isomerized to dimethyl fumarate under the reaction conditions.
The amine-catalyzed isomerization of dimethyl maleate into dimethyl fumarate involves the aza-Michael reaction, which is the addition of an amine to an electron-deficient C=C double bond.
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