Find Dimethyl fumarate (624-49-7) on LEAPChem.com!
Nov. 2018/3/8 14:31:00 By LEAP Chem
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Basic Information of Dimethyl fumarate
Chemical Name: Dimethyl fumarate
Cas No.: 624-49-7
Molecular Formula: C6H8O4
Dimethyl fumarate (DMF) is the methyl ester of fumaric acid. DMF was initially recognized as a very effective hypoxic cell radiosensitizer. Later, DMF combined with three other fumaric acid esters (FAE) was licensed in Germany as oral therapy for psoriasis (trade name Fumaderm). Other diseases, such as necrobiosis lipoidica, granuloma annulare, and sarcoidosis were also found to respond to treatment with DMF in case reports or small patient series. Phase III clinical trials found that DMF (BG-12) successfully reduced relapse rate and increased time to progression of disability in multiple sclerosis (trade name Tecfidera). DMF is thought to have immunomodulatory properties without significant immunosuppression.
Dimethyl fumarate was shown to have a significant effect on relapse rate and time to progression in phase III clinical trials of multiple sclerosis. Several methods exist for the laboratory synthesis of dimethyl fumarate, with reported methods alkene isomerization of dimethyl maleate, and Fischer esterification of fumaric acid. Dimethyl fumarate is an ester and an α,β-unsaturated electrophilic compound which can quickly undergo Michael additions with nucleophiles. Dimethyl fumarate is also an effective diene acceptor in the thermal Diels-Alder reaction, where the reactivity of its vinylenic bond is enhanced by the two electron-withdrawing ester groups. Due to the geometry of the starting ester, the Diels-Alder product will have a trans configuration. With this reaction, compounds with bicyclo skeletons can be synthesized, e.g. a diester with a norbornene skeleton from dimethyl fumarate and cyclopentadiene.
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