Dimethyl fumarate
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| Dimethyl fumarate | |
|---|---|
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| IUPAC name | Dimethyl (E)-butenedioate |
| Other names | trans-1,2-Ethylenedicarboxylic acid, dimethyl ester 2-Butenedioic acid, dimethyl ester |
| Identifiers | |
| CAS number | [624-49-7] |
| EINECS number | |
| SMILES | C(=C/C(=O)OC)\C(=O)OC |
| Properties | |
| Molecular formula | C6H8O4 |
| Molar mass | 144.127 g/mol |
| Appearance | White crystalline solid |
| Density | 1.37 g/cm³, solid |
| Melting point |
102-105 °C[1] |
| Boiling point |
192-193 °C[1] |
| Hazards | |
| EU classification | Harmful (Xn) |
| R-phrases | R21 R38 R41 R43 |
| S-phrases | S26 S36 S37 S39 |
| Related compounds | |
| Related diesters | Diethyl fumarate, dimethyl maleate, dimethyl malonate, dimethyl adipate |
| Related compounds | Fumaric acid Methyl acrylate |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Dimethyl fumarate is the methyl ester of fumaric acid.
Contents |
[edit] Reactions
Dimethyl fumarate is an ester and an α,β-unsaturated electrophilic compound, undergoing reactions typical to them. It is also a diene acceptor in the ordinary Diels-Alder reaction, where the reactivity of its vinylidenic bond is enchanced by the two electron-withdrawing ester groups. Due to its geometry, the Diels-Alder product has a trans configuration.
[edit] Uses
Dimethyl fumarate is used to treat psoriasis. It is a lipophilic, highly mobile molecule in human tissue. However, as an α,β-unsaturated ester, dimethyl fumarate reacts rapidly with the detoxifying agent glutathione by Michael addition. When administered orally, it does not survive long enough to be absorbed into blood.[2]
Another use for dimethyl fumarate is mold inhibition.
[edit] Risks
Dimethyl fumarate has been found to be a sensitizer at very low concentrations, producing extensive, pronounced eczema that is difficult to treat. There are only a handful of equally potent sensitizers. The extreme sensitizing risk was brought to public attention by the "poison chair" incident, where 60 patients were diagnosed with allergic eczema.[3] Dimethyl fumarate was used as a mold inhibitor. The chairs were sold in 2006-2007 and produced by a Chinese manufacturer.
[edit] References
[edit] External links
- Dimethyl fumarate Material Safety Data Sheet (MSDS)
