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Dimethyl fumarate

Basic information Fungicides Chemical Properties Medical use Uses Production method Chemical Properties Uses Uses Definition Safety Related Supplier
Dimethyl fumarate Basic information
Dimethyl fumarate Chemical Properties
  • Melting point:102-106 °C(lit.)
  • Boiling point:192-193 °C(lit.)
  • Density 1,37 g/cm3
  • Flash point:192-193°C
  • storage temp. Store at RT.
  • solubility 1.6g/l
  • form Liquid
  • color Clear colorless to faintly yellow
  • PH4.0-6.0 (10g/l, H2O, 20℃)suspension
  • Water Solubility Soluble in water (1.6 mg/ml at 20°C), methanol (30-36 mg/ml), ethanol (10 mg/ml at 25°C), DMSO (29 mg/ml at 25°C), and DMF (~12 mg/ml).
  • Merck 14,4287
  • BRN 774590
  • Stability:Stable. Incompatible with acids, bases, oxidizing agents, reducing agents.
  • CAS DataBase Reference624-49-7(CAS DataBase Reference)
  • NIST Chemistry Reference2-Butenedioic acid (E)-, dimethyl ester(624-49-7)
  • EPA Substance Registry System2-Butenedioic acid (2E)-, dimethyl ester(624-49-7)
Safety Information
MSDS
Dimethyl fumarate Usage And Synthesis
  • FungicidesDimethyl fumarate is a new type of air fungicides . At room temperature ,it is white crystalline powder, melting point is 102~104 ℃, specific gravity of 1.37, slightly soluble in water, soluble in ethyl acetate, chloroform and alcohol, sublime, low toxicity, rat oral 50 = 2628mg/kg, maximum no effect dose is 50mg/kg, with a broad spectrum, high efficiency, low toxicity, low cost, etc.In addition to good bacteriostatic and sterilization effects , it also has insecticidal effect. It has both contact sterilization and fumigation sterilization effects. The product uses are highly secure,there is no residue after metabolism in humans and animals. Several examples demonstrate, dimethyl fumarate can be contacted through the skin, causing serious reactions or allergies and other skin burning. In addition, the product is also irritating,it should be avoid ed contacting with eyes.
    application:
    1. Food mildew proof. DMF is used for bread, moon cake, cake and other food mildew proof, it has good preservation effect. The amount is only 0.05%.
    2. Grain storage. An appropriate amount of DMF is added directly to rice, flour, and the preservation time is more than 200 days,it can also kill Tribolium castaneum Herbst,sitophilus zeamais motschulsky , lesser grain borer,Flat Grain Beetle, etc.in the grain , to ensure the quality of food storage.
    3. Feed mildew proof. The vanqulishingmold whose formulation is based on DMF is an efficient feed fungicide .
    4. Preservation of fruits, it has a outstanding effect especially on citrus.
    5. Cocoon mildew proof.
    6. Clothes moth and mildew proof.
    The above information is edited by the chemicalbook of Tian Ye.
  • Chemical PropertiesCrystalline powder. Melting point 103-104 ℃, the boiling point of 193 ℃. The relative density of 1.37. It is soluble in ethyl acetate, chloroform, acetone and alcohols, ether-soluble and insoluble in water. Rats by oral LD502.628g/kg.
  • Medical useDimethyl fumarate (DMF) (BG-12, Tecfidera) is an oral fumaric acid ester (FAE) that is frequently prescribed for treatment of relapsing forms of multiple sclerosis (MS). DMF was developed for treatment of MS based upon knowledge that Fumaderm, a combination of DMF and monoethyl fumarate used in treatment of psoriasis, exhibits immunomodulatory and antioxidative properties. Dimethylfumarate and its metabolite methylhydrogenfumarate are the pharmacologically active compounds, with Dimethylfumarate being the main component of the marketed fumaric-mixture. It is a lipophilic, highly mobile molecule in human tissue. The medications in which the Dimethylfumarate is being used, slow down both the accelerated cell division and the inflammatory activity in the skin.
    In 2012 a trial showed that a drug called BG-12 used for psoriasis, a skin problem, also worked against MS. In 2013 it was given the new name of dimethyl fumarate (DMF) and a licence to be used in the UK to treat relapsing MS. In 2014 the National Institute for Health and Care Excellence (NICE) gave the go ahead for the drug to be used on the NHS. Dimethyl fumarate is pronounced: dye-METH-ul FUME-er-ayt. Its brand name is Tecfidera (teckfer-DAIR-ah).
    Dimethyl fumarate is recommended for the treatment of 'active' relapsing MS, defined in guidelines as two or more relapses in the last two years. But more and more MS specialists define ‘active’ MS as one recent relapse and/ or signs on MRI scans that MS is active.
  • Uses
    1. Dimethyl fumarate is an anti-inflammatory. It is indicated for multiple sclerosis patients with relapsing forms and is also being investigated for the treatment of psoriasis.
    2. Dimethyl fumarate (TECFIDERA) is an orally administered fumarate ester recently FDA approved for first-line monotherapy of multiple sclerosis. Because it is rapidly and completely hydrolyzed by esterases before reaching the systemic circulation, the pharmacologic activity of dimethyl fumarate is due to its active metabolite, monomethyl fumarate.The mechanism of action of dimethyl fumarate in multiple sclerosis is not well understood. It is thought to involve dimethyl fumarate degradation to its active metabolite monomethyl fumarate (MMF) then MMF up-regulates the Nuclear factor (erythroid-derived 2)-like 2 (Nrf2) pathway that is activated in response to oxidative stress.
    3. Dimethyl fumarate is a lipophilic electrophile that has profound effects on oxidative and immunological pathways.
    4. It rapidly interacts in a Michael addition reaction with glutathione or is metabolized to monomethyl fumarate.
    5. Dimethyl fumarate at low micromolar levels activates the nuclear factor erythroid 2-related factor 2 (Nrf2), resulting in an antioxidant response featuring heme oxygenase-1 expression and increased glutathione levels.1 It also suppresses the expression of pro-inflammatory cytokines and inhibits angiogenesis.2,3 Through these actions dimethyl fumarate alters the course of psoriasis and may reduce inflammation related to multiple sclerosis.
    6. It is widely used in food, grain ,feed, tobacco, leather and clothing and other for anti-corrosion anti-mildew and preservation.
    7. Dimethyl fumarate has an effect which can slowly and effectively stifle mildew in a long time.
  • Production methodProduction method 1.
    Esterification of fumaric acid. Directly use fumaric acid as raw materials, in the presence of catalysts ,it reacts with methanol and synthesize DMF in one step . Catalysts are boron trifluoride, ferric chloride hexahydrate (FeCl3 · 6H2O), sulfuric acid or phosphoric acid, the yield rate is up to 92%. You can also use cationic resin as the catalyst, apply catalytic distillation technology, the esterification reaction lasts 5h at 80-85 ℃ .
    Production method 2.
    Isomerization of maleic acid esterification. Maleic acid and methanol in the presence of catalysts, after isomerization, esterification ,DMF is produced, catalysts are HCl-H2SO4 and phosphotungstic acid. When using HCl-H2SO4 as a catalyst , the actual reaction is in two steps, the HCl catalytic isomerization reaction and H2SO4 catalyzed esterification . Maleic acid with concentrated hydrochloric acid, water, flow back together for 30min, obtain 91% of fumaric acid; fumaric acid with methanol, concentrated sulfuric acid reflux for 12h, obtain 91.9% of the product. Phosphotungstic acid is the composite catalyst, it has catalytic isomerization and esterification effects at the same time. Maleic acid with methanol, in the presence of phosphotungstic acid ,reflux for 4h, the product is 89.4%.
    Production method 3.
    Furfural oxidation esterification. Use furfural as material,the synthesis is in two steps. First, at uronic V2O5 catalytic, after KClO3 oxidation , fumaric acid is produced, the reaction temperature is 95 ℃-105 ℃, reaction time is 7H , the yield rate is 81.5%; in the presence of concentrated sulfuric acid,fumaric acid is heated and refluxed with methanol to generate DMF, the reaction time is 10h. The yield rate is 86.0%.
    Production method 4.
    Hydrolysis of maleic anhydride heterogeneous esterification. Maleic anhydride is used as a raw material,it reacts with methanol to produce DMF in the presence of catalysts. The catalysts are concentrated hydrochloric acid, hydrochloric acid-phosphoric acid, ferric chloride hexahydrate, methyl acid and thiourea. Hydrochloric acid-phosphoric acid catalyst is a composite catalyst, hydrolysis, esterification occur first, obtain dimethyl maleate, which then in the presence of light and bromine after isomerization ,obtain the product; use thiourea as catalyst, maleic anhydride occurs first hydrolysis isomerization reaction to obtain fumaric acid , which in the presence of sulfuric acid, generate the products after esterification .
    Example: add 9.8g (0.1mol) of maleic anhydride, 8.1mL (0.2mol) methanol, 0.5mL concentrated sulfuric acid in 100mL flask, then heat and reflux for 1.5h. Then drop 12Ml (0.3mol) excess methanol, 0.5h After the dropping, continue refluxing for 2h. After completion of the reaction the methanol is evaporated, ethanol is added 30mL coolish, heat to dissolve the solid, cool to precipitate crystals. Two products are recrystallized once with ethanol and water respectively to give the product 12.3g, a yield rate of 86.2% Melting point 103-104 ℃.
  • Chemical Propertiesfine white crystalline powder
  • Usesimmunomodulator
  • Usestrans-1,2-Ethylenedicarboxylic Acid is used in cycloaddition reactions involving ylides, benzenes and amino acids.
  • DefinitionChEBI: An enoate ester resulting from the formal condensation of both carboxy groups of fumaric acid with methanol. Used for treatment of adults with relapsing forms of multiple sclerosis.
Dimethyl fumarate Preparation Products And Raw materials
Dimethyl fumarate(624-49-7)Related Product Information
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