Monomethyl fumarate

Base Information

• Chemical Name: Monomethyl fumarate
• CAS No.: 2756-87-8
• Molecular Formula: C5H6O4
• Molecular Weight: 130.1
• Hs Code.: 29171900
• European Community (EC) Number: 220-412-6
• UNII: 45IUB1PX8R
• DSSTox Substance ID: DTXSID801016498
• Nikkaji Number: J121.400D,J520.491G
• Wikipedia: Monomethyl_fumarate
• Wikidata: Q27087639
• NCI Thesaurus Code: C166722
• RXCUI: 1546433
• Pharos Ligand ID: 1UAZQW1QGA4J
• Metabolomics Workbench ID: 143142
• ChEMBL ID: CHEMBL589586
• Mol file: 2756-87-8.mol

Synonyms:2-Butenedioicacid (2E)-, monomethyl ester (9CI);2-Butenedioic acid (E)-, monomethyl ester;Fumaric acid, methyl ester (6CI,7CI);Fumaric acid, monomethyl ester (8CI);Methyl hydrogen fumarate;2-Butenedioic acid(2E)-, 1-methyl ester;

Chemical Property of Monomethyl fumarate

Chemical Property:

• Vapor Pressure: 0.00706mmHg at 25°C
• Melting Point: 144-145 °C(lit.)
• Refractive Index: 1.468
• Boiling Point: 249.959 °C at 760 mmHg
• PKA: 3.40±0.10(Predicted)
• Flash Point: 108.944 °C
• PSA: 63.60000
• Density: 1.266 g/cm³
• LogP: -0.19980
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 130.02660867
• Heavy Atom Count: 9
• Complexity: 147

Purity/Quality:

98% ^*data from raw suppliers

FumaricAcidMonomethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C=CC(=O)O
• Isomeric SMILES: COC(=O)/C=C/C(=O)O
• Recent ClinicalTrials: Comparative Bioavailability of BAFIERTAM? (Monomethyl Fumarate) and Tecfidera? (Dimethyl Fumarate) in Healthy Subjects
• Description: Monomethyl fumarate (MMF), a bioactive metabolite of fumaric acid ester, is an immunotherapy for psoriasis that causes decreased production of Th1 cytokines and lymphocytopenia. Monomethyl fumarate was shown to decrease DC response to LPS and decreased IL-12p70 and IL-10 production.
• Uses: Monomethyl fumarate is used to treat the relapsing forms of multiple sclerosis (MS), including clinically isolated syndrome, relapsing-remitting disease, and active secondary progressive disease. This medicine will not cure MS, but it may slow some of the disabling effects and decrease the number of relapses of the disease.Fumaric Acid Monomethyl Ester is one of the most bioactive anti-psoriatic fumaric acid ester metabolite. Fumaric Acid Monomethyl Ester is potent nicotinic acid receptor agonist. Fumaric Acid Monomethy l Ester has also been shown to selectively stimulate of T helper 2 cytokine response.

Technology Process of Monomethyl fumarate

There total 24 articles about Monomethyl 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: 98.0%

monomethyl maleate (3052-50-4) → methyl hydrogen fumarate (2756-87-8)

Guidance literature:

at 200 ℃; for 0.25h; microwave irradiation;

DOI:10.1016/j.tet.2006.10.074

Reference yield: 92.2%

maleic anhydride (108-31-6) + methanol (67-56-1) → methyl hydrogen fumarate (2756-87-8)

Guidance literature:

With thiourea; at 40 ℃; for 0.5h; Temperature;

DOI:10.1039/c9ra09119j

Reference yield: 87.0%

dimethylfumarate (624-49-7) → methyl hydrogen fumarate (2756-87-8)

Guidance literature:

With lithium hydroxide; In water; acetone; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2005.05.114

upstream raw materials:

methanol

methyl 5-nitrofuran-2-carboxylate

sodium methylate

monomethyl maleate

Downstream raw materials:

(E)-But-2-enedioic acid cyclohex-2-enyl ester methyl ester

(E)-But-2-enedioic acid methyl ester (E)-3-(2,6,6-trimethyl-cyclohex-1-enyl)-allyl ester

tricyclo<3.3.1.1^3,7>dec-2-yl *,R^*)>-3-(1H-indol-3-ylmethyl)-3-methyl-4,9,12-trioxo-7-phenyl-13-oxa-2,5,8-triazatetradec-10-enoate

tricyclo<3.3.1.1^3,7>dec-2-yl *,S^*(E)>>-3-(1H-indol-3-ylmethyl)-3-methyl-4,9,12-trioxo-6-(phenylmethyl)-13-oxa-2,5,8-triazatetradec-10-enoate

Refernces

• 1、 Hurst,J.K.,Taube,H.. "-". . p. 1178 - 1186. Retrieved 1968.
• 2、 -. "PROCESS FOR PREPARATION OF DIROXIMEL FUMARATE". Paragraph 0143. . Retrieved 2021/04/01.
• 3、 -. "AN IMPROVED PROCESS FOR THE SYNTHESIS OF DIMETHYL FUMARATE". Paragraph 0027. . Retrieved 2017/05/10.