Dimethyl fumarate #CAS624-49-7
Dimethyl fumarate #CAS624-49-7
Dimethyl fumarate[DMF] is the methyl ester of fumaric acid. DMF, marketed in Germany under the trade name of Fumaderm, is used for oral therapy of psoriasis in combination with other drugs. Later it has been used to treat adults with relapsing multiple sclerosis[a chronic inflammatory, demyelinating and neurodegenerative disease of the CNS resulting in neurological disability] since 2013(trade name Tecfidera). DMF is thought to have immunomodulatory properties without significant immunosuppression. In preclinical studies, dimethyl fumarate exhibited anti-inflammatory and cytoprotective properties that are generally thought to be mediated via activation of the nuclear factor [erythroid-derived 2]-like 2 transcriptional pathway, which is involved in the cellular response to oxidative stress.
In a non-medical use, DMF has been used as a biocide in furniture or shoes to prevent growths of mold during storage or transport in a humid climate. However, due to incidences of allergic reactions after skin contact the European Union has banned DMF in consumer products since 1998, and since January 2009 the import of products containing DMF has also been banned.
Dimethyl fumarate is a novel oral therapeutic agent, which can be used for patients suffering from relapsing-remitting multiple sclerosis. It shows an effective inhibition of mould in bread and can also serve as a potential candidate for the treatment of psoriasis, a chronic autoimmune condition.
ChEBI: Dimethyl fumarate is 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. It has a role as an immunomodulator and an antipsoriatic. It is an enoate ester, a methyl ester and a diester. It is functionally related to a methanol and a fumaric acid.
Dimethyl fumarate is a novel oral therapeutic agent, which can be used for patients suffering from relapsing-remitting multiple sclerosis. It shows an effective inhibition of mould in bread and can also serve as a potential candidate for the treatment of psoriasis, a chronic autoimmune condition.
Application of Dimethyl fumarate
Dimethyl fumarate acts as an immunomodulator. It is also used in cycloaddition reactions involving ylides, benzenes and amino acids. It is added to food grains,tobacco,leather and preservation. Clothing
Treatment of relapsing-remitting multiple sclerosis
Treatment of moderate to severe plaque psoriasis
| Dimethyl fumarate Chemical Properties |
| Melting point | 102-106 °C (lit.) |
| Boiling point | 192-193 °C (lit.) |
| density | 1,37 g/cm3 |
| vapor pressure | 5 hPa (25 °C) |
| refractive index | 1.4062 (estimate) |
| Fp | 192-193°C |
| storage temp. | Store below +30°C. |
| solubility | 1.6g/l |
| form | Liquid |
| color | Clear colorless to faintly yellow |
| PH | 4.0-6.0 (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 |
| Henry's Law Constant | 1.4×101 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stability: | Stable. Incompatible with acids, bases, oxidizing agents, reducing agents. |
| InChI | 1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+ |
| InChIKey | LDCRTTXIJACKKU-ONEGZZNKSA-N |
| SMILES | [H]\C(=C(\[H])C(=O)OC)C(=O)OC |
| CAS DataBase Reference | 624-49-7(CAS DataBase Reference) |
| NIST Chemistry Reference | 2-Butenedioic acid (E)-, dimethyl ester(624-49-7) |
| EPA Substance Registry System | 2-Butenedioic acid (2E)-, 1,4-dimethyl ester (624-49-7) |
| Safety Information |
| Hazard Codes | Xn |
| Risk Statements | 21-38-41-43-36/37/38-36/38 |
| Safety Statements | 26-36/37/39-36/37 |
| RIDADR | UN 3077 9 / PGIII |
| WGK Germany | 1 |
| RTECS | EM6125000 |
| TSCA | TSCA listed |
| HazardClass | 9 |
| HS Code | 29171990 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Dermal Aquatic Chronic 2 Skin Irrit. 2 Skin Sens. 1 STOT SE 3 |
| Hazardous Substances Data | 624-49-7(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 2240 mg/kg LD50 dermal Rabbit 1250 mg/kg |
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