Monoethyl fumarate

Base Information

• Chemical Name: Monoethyl fumarate
• CAS No.: 2459-05-4
• Molecular Formula: C6H8 O4
• Molecular Weight: 144.127
• Hs Code.: 29171900
• European Community (EC) Number: 219-544-7
• NSC Number: 244252
• UNII: Y3W849NG2N
• DSSTox Substance ID: DTXSID701021503
• Nikkaji Number: J121.401B,J443.405F
• Wikidata: Q27294232
• Metabolomics Workbench ID: 124397
• ChEMBL ID: CHEMBL1771637
• Mol file: 2459-05-4.mol

Synonyms:calcium monoethylfumarate;ethyl fumarate;ethyl fumarate, 2 copper salt;ethyl fumarate, 2 ferrium salt;ethyl fumarate, calcium salt;ethyl fumarate, lithium salt;ethyl fumarate, maganeese salt;ethyl fumarate, sodium salt;ethyl fumarate, zinc salt;ethylhydrogenfumarate;fumaric acid monoethyl ester;monoethyl fumarate;zinc monoethylfumarate

Chemical Property of Monoethyl fumarate

Chemical Property:

• Appearance/Colour: almost white to beige cryatalline power
• Vapor Pressure: 0.0034mmHg at 25°C
• Melting Point: 66-68 °C(lit.)
• Refractive Index: 1.4500 (estimate)
• Boiling Point: 261.6 °C at 760 mmHg
• PKA: 3.45±0.10(Predicted)
• Flash Point: 109.6 °C
• PSA: 63.60000
• Density: 1.208 g/cm³
• LogP: 0.19030
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in water.
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 144.04225873
• Heavy Atom Count: 10
• Complexity: 159

Purity/Quality:

99% ^*data from raw suppliers

Fumaric Acid Monoethyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C=CC(=O)O
• Isomeric SMILES: CCOC(=O)/C=C/C(=O)O
• 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.
• 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.

Technology Process of Monoethyl fumarate

There total 25 articles about Monoethyl fumarate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

diethyl Fumarate (623-91-6) → (E)-4-ethoxy-4-oxobut-2-enoic acid (2459-05-4)

Guidance literature:

With potassium hydroxide; In ethanol; for 8h; Ambient temperature;

DOI:10.1080/00397919708004135

Reference yield: 87.0%

ethyl acetate (141-78-6) + maleic acid (110-16-7,26099-09-2) → (E)-4-ethoxy-4-oxobut-2-enoic acid (2459-05-4)

Guidance literature:

With iron(III) perchlorate; for 2h; Ambient temperature;

Reference yield: 76.0%

ethyl (2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate (1009307-13-4) + carbon dioxide (124-38-9,18923-20-1) → (E)-4-ethoxy-4-oxobut-2-enoic acid (2459-05-4)

Guidance literature:

With potassium methanolate; copper(l) chloride; In N,N-dimethyl acetamide; at 70 ℃; for 24h; Sealed tube; Schlenk technique;

upstream raw materials:

maleic anhydride

ethanol

ethyl iodide

diethyl ether

Downstream raw materials:

methyl hydrogen fumarate

ethyl<3-(2,3-dihydro-1,4-dioxin-5-yl)-2,4,4-trimethyl>cyclohex-2-enylbut-2-enedioate

ethyl (2E,4E)-hexa-2,4-dien-1-yl fumarate

2-(2'-ethoxycarbonyl)acryloyl-3-phenyl-l-menthopyrazole

Refernces

• 1、 Spatz,Stone. "-". . p. 1559,1560. Retrieved 1958.
• 2、 -. "Application of fumaric acid monoethyl ester silver salt in preventing novel coronavirus infections". Paragraph 0022. . Retrieved 2020/06/09.
• 3、 Hong, Junting,Nayal, Onkar S.,Mo, Fanyang. "Carboxylation of Alkenyl Boronic Acids and Alkenyl Boronic Acid Pinacol Esters with CO2 Catalyzed by Cuprous Halide". supporting information. p. 2813 - 2818. Retrieved 2020/05/16.