2459-05-4

Hazard Information

Chemical Properties

ALMOST WHITE TO BEIGE CRYSTALLINE POWDER

Uses

Monoethyl fumarate is the monoethyl ester form of fumaric acid. Monoethyl fumarate is a kind of effective preservative and polymerization agent for macromolecular material.
Monoethyl fumarate (fumaric acid monoethyl ester, monoethyl fumarate) was used in the preparation of photo-crosslinkable macromers. It was also used to synthesize Ugi/intramolecular Diels-Alder (IMDA) cycloaddition products.

Definition

ChEBI: Monomethyl fumarate is a dicarboxylic acid monoester resulting from the formal condensation of one of the carboxy groups of fumaric acid with methanol. Is is a metabolite of dimethyl fumarate and used for the the treatment of patients with relapsing multiple sclerosis (MS). It also induces the NFE2L2 (Nrf2) transcription factor by binding to KEAP1. It has a role as an immunomodulator, an antioxidant and a drug metabolite. It is an enoate ester, a methyl ester and a dicarboxylic acid monoester. It derives from a fumaric acid.

Preparation

Monomethyl fumarate was synthesized by maleic anhydride and methanol. It is used to treat relapsing forms of multiple sclerosis in adults (including clinically isolated syndrome, relapsing-remitting disease, and active secondary progressive disease).

Synthesis

2459-05-4

2459-05-4

General method: anhydrous AlCl3 (0.16 g) was slowly added to monoethyl cis-but-2-enedioate (4 g) under stirring conditions. The reaction mixture was warmed up to 60-70°C and maintained for 0.5-2 hours. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently diluted with 1N HCl (30 mL). The diluted mixture was separated from the aqueous phase and the aqueous portion was extracted with ethyl acetate (3 x 40 mL). The organic extracts were combined, washed sequentially with brine (2 × 20 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give the crude product monoethyl trans-but-2-enedioate.

Questions And Answer

• Description

  Monoethyl fumarate is the Monoethyl ester form of fumarate. It is a kind of effective preservative and polymerization agent for macromolecular material. Monoethyl fumarate is capable of inhibiting the growth of bacteria, yeast and mold and prolonging the storage time of feed can. It can also be used for long-term systemic therapy in the treatment of psoriasis (a chronic hyperproliferative inflammatory skin disorder). It is the most active ingredient in the antipsoriasis drug Fumadem. The mechanism is likely to be related to its effect of improvement of keratinocyte differentiation and inhibition of keratinocyte proliferation. Monomethyl fumarate has beneficial effects on the inflamed blood–brain barrier. It increases levels of endogenous antioxidant proteins in brain endothelial cells and reduces expression of VCAM-1 in inflamed brain endothelial cells. Transendothelial monocyte migration is limited upon MMF treatment. ;

• References

  Thio, H. B., et al. "Long‐term systemic therapy with dimethylfumarate and monoethylfumarate (Fumaderm®;) in psoriasis." Journal of the European Academy of Dermatology & Venereology 4.1(1995):35-40.
  Asadullah, K, et al. "Influence of monomethylfumarate on monocytic cytokine formation--explanation for adverse and therapeutic effects in psoriasis?." Archives of Dermatological Research 289.11(1997):623-30.
  Lim, J. L., et al. "Protective effects of monomethyl fumarate at the inflamed blood-brain barrier." Microvascular Research 105(2016):61.
  Zhao, Wen Xiu, C. M. Zhang, and X. U. Xue-Ming. "Synthesis and antimicrobial active of monomethyl fumarate." Science & Technology of Food Industry (2008).
  Helwa, Inas. "The Mechanism of Monomethylfumarate (MMF) as an Anti-psoriatic Agent." Helwa Inas (2014) ;

Spectrum Detail

Well-known Reagent Company Product Information

Supplier

Related Products