Basic information Description References Safety Supplier Related
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Monoethyl fumarate

Basic information Description References Safety Supplier Related

Monoethyl fumarate Basic information

Product Name:
Monoethyl fumarate
Synonyms:
  • (2E)-4-Ethoxy-4-oxo-2-butenoic acid
  • 2-Butenedioic acid (E)-, monoethyl ester
  • Mono-Ethyl fuMarate 95%
  • Mono-Ethyl FuMarate, 97+%
  • (2E)-2-Butenedioic Acid Monoethyl Ester
  • FuMaric Acid Ethyl Ester
  • Monoethyl FuMerate
  • Monoethyl trans-2-Butenedioate
CAS:
2459-05-4
MF:
C6H8O4
MW:
144.13
EINECS:
219-544-7
Product Categories:
  • mildew preventive
  • Building Blocks
  • C6 to C7
  • Carbonyl Compounds
  • Chemical Synthesis
  • Esters
  • Organic Building Blocks
  • bc0001
Mol File:
2459-05-4.mol
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Monoethyl fumarate Chemical Properties

Melting point:
66-68 °C (lit.)
Boiling point:
147 °C/16 mmHg (lit.)
Density 
1.1109
refractive index 
1.4500 (estimate)
storage temp. 
Refrigerator
solubility 
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
pka
3.45±0.10(Predicted)
form 
Crystalline Powder
color 
Almost white to beige
Water Solubility 
Soluble in water.
BRN 
1723588
Dielectric constant
6.5(23.0℃)
CAS DataBase Reference
2459-05-4(CAS DataBase Reference)
NIST Chemistry Reference
Ethyl hydrogen fumarate(2459-05-4)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
1
HazardClass 
IRRITANT
HS Code 
29171900

MSDS

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Monoethyl fumarate Usage And Synthesis

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)

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).

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