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Monoethyl fumarate

CAS No.
2459-05-4
Chemical Name:
Monoethyl fumarate
Synonyms
AKOS BBB/201;Ethylfumarat;ETHYL FUMARATE;Monoethyl FuMerate;MONOETHYL FUMARATE;monoethyl furmarate;ETHYL ACID FUMARATE;RARECHEM AL BE 1505;MonoethylFumarate>Mono-Ethyl fuMarate 95%
CBNumber:
CB7231119
Molecular Formula:
C6H8O4
Molecular Weight:
144.13
MDL Number:
MFCD00002699
MOL File:
2459-05-4.mol
MSDS File:
SDS
Last updated:2024-02-18 17:28:16

Monoethyl fumarate 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)
form Crystalline Powder
pka 3.45±0.10(Predicted)
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)
FDA UNII Y3W849NG2N
NIST Chemistry Reference Ethyl hydrogen fumarate(2459-05-4)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H317-H319-H335
Precautionary statements  P280-P302+P352-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36
WGK Germany  1
HazardClass  IRRITANT
HS Code  29171900
NFPA 704
1
2 0

Monoethyl fumarate price More Price(25)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 92585 mono-Ethyl fumarate certified reference material, TraceCERT 2459-05-4 50mg $84.1 2024-03-01 Buy
Sigma-Aldrich 128422 mono-Ethyl fumarate 95% 2459-05-4 25g $70.9 2024-03-01 Buy
TCI Chemical F0359 Monoethyl Fumarate >97.0%(GC)(T) 2459-05-4 25g $97 2024-03-01 Buy
TCI Chemical F0359 Monoethyl Fumarate >97.0%(GC)(T) 2459-05-4 250g $676 2024-03-01 Buy
Usbiological 012149 Fumaric Acid Monoethyl Ester 2459-05-4 1g $319 2021-12-16 Buy
Product number Packaging Price Buy
92585 50mg $84.1 Buy
128422 25g $70.9 Buy
F0359 25g $97 Buy
F0359 250g $676 Buy
012149 1g $319 Buy

Monoethyl fumarate Chemical Properties,Uses,Production

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).

1009307-13-4
124-38-9
2459-05-4
Synthesis of Monoethyl fumarate from 2-ETHOXYCARBONYLVINYLBORONIC ACID PINACOL ESTER and Carbon dioxide
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View Lastest Price from Monoethyl fumarate manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Monoethyl fumarate pictures 2023-10-23 Monoethyl fumarate
2459-05-4
US $20.00-10.00 / kg 1kg 0.99 20 tons Hebei Yanxi Chemical Co., Ltd.
Monoethyl fumarate pictures 2023-10-09 Monoethyl fumarate
2459-05-4
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
Monoethyl fumarate pictures 2023-09-06 Monoethyl fumarate
2459-05-4
US $0.00-0.00 / KG 1KG 99% 500000kg Hebei Guanlang Biotechnology Co., Ltd.
(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 Ethyl Hydrogen Fumarate Fumaric Acid Monoethyl Ester Monoethyl FuMarate (Quetiapine IMpurity R) monoethyl furmarate Fumaric acid monoethyleester ETHYL ACID FUMARATE ETHYL HYDROGEN FUMARATE ETHYL FUMARATE ETHYL FUMARATE MONOESTER FUMARIC ACID MONOETHYL ESTER AKOS BBB/201 RARECHEM AL BE 1505 MONOETHYL FUMARATE (E)-2-ButenedioicAcidMono-EtEster Ethyl hydrogen fumarate, 97+% 2-Butenedioic acid (2E)-, monoethyl ester (2E)-2-Butenedioic Acid 1-Ethyl Ester Ethylfumarat Fumaric Acid Monoethyl Ester 2459-5-4 Fumaric acid monoethyl ester, Monoethyl fumarate (E)-2-Butenedioic acid hydrogen 1-ethyl ester Fumaric acid 1-hydrogen 4-ethyl ester Fumaric acid hydrogen 1-ethyl ester Monoethyl trans-ethylene-1,2-dicarboxylate Fumaric acid monoethyl ester,95% (2E)-4-Ethoxy-4-oxobut-2-enoic acid 2-Butenedioic acid (2E)-, 1-ethyl ester Quetiapine Impurity 33(Quetiapine EP Impurity R) (E)-4-ethoxy-4-oxo-2-butenoate MonoethylFumarate> Monoethyl fumarate ISO 9001:2015 REACH Quetiapine EP Impurity R (Fumaric Acid Monoethyl Ester) Monoethyl FumarateQ: What is Monoethyl Fumarate Q: What is the CAS Number of Monoethyl Fumarate Q: What is the storage condition of Monoethyl Fumarate Q: What are the applications of Monoethyl Fumarate 2459-05-4 204296 204-29-6 2459-05-04 9004-32-6 C2H5OCOCHCHCOOH C6H804 HOOCCHCHCOOC2H5 CHCOOC2H52 C6H7O4 CARBOXYLIC ACID Organic Building Blocks EQ - EZ Esters Carbonyl Compounds C6 to C7 Building Blocks Analytical Standards