2459-05-4 Usage
Description
Monoethyl fumarate, also known as fumaric acid monoethyl ester, is a dicarboxylic acid monoester derived from the formal condensation of one of the carboxy groups of fumaric acid with ethanol. It is an almost white to beige crystalline powder and is recognized for its effectiveness as a preservative and polymerization agent for macromolecular materials. Monoethyl fumarate exhibits properties that enable it to inhibit the growth of bacteria, yeast, and mold, as well as improve keratinocyte differentiation and inhibit keratinocyte proliferation, making it a promising candidate for various applications.
Uses
Used in Pharmaceutical Industry:
Monoethyl fumarate is used as an active ingredient in the antipsoriasis drug Fumadem for long-term systemic therapy in the treatment of psoriasis, a chronic hyperproliferative inflammatory skin disorder. Its application is due to its ability to improve keratinocyte differentiation and inhibit keratinocyte proliferation.
Used in Feed Industry:
Monoethyl fumarate is used as an effective preservative for the feed industry, as it can inhibit the growth of bacteria, yeast, and mold, thereby prolonging the storage time of feed can.
Used in Polymer Industry:
As a polymerization agent for macromolecular materials, Monoethyl fumarate is utilized in the preparation of photo-crosslinkable macromers, contributing to the development of advanced polymer materials with specific properties.
Used in Chemical Synthesis:
Monoethyl fumarate is employed in the synthesis of Ugi/intramolecular Diels-Alder (IMDA) cycloaddition products, showcasing its versatility in chemical reactions and the creation of complex molecular structures.
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)
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).
Check Digit Verification of cas no
The CAS Registry Mumber 2459-05-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,4,5 and 9 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 2459-05:
(6*2)+(5*4)+(4*5)+(3*9)+(2*0)+(1*5)=84
84 % 10 = 4
So 2459-05-4 is a valid CAS Registry Number.
InChI:InChI=1/C6H8O4/c1-2-10-6(9)4-3-5(7)8/h3-4H,2H2,1H3,(H,7,8)/p-1
2459-05-4Relevant articles and documents
Action of alpha-chymotrypsin on the diethyl esters of fumaric, maleic, and acetylenedicarboxylic acids.
Cohen,Klee,Weinstein
, p. 5302 - 5305 (1966)
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Kras-G12C inhibitor heterocyclic compounds
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Paragraph 0239; 0242-0245, (2021/06/23)
The invention relates to Kras-G12C inhibitor heterocyclic compounds represented by formula I, a preparation method thereof, and application of the Kras-G12C inhibitor heterocyclic compounds in prevention and treatment of tumor diseases such as lung cancer, colorectal cancer and pancreatic cancer. In the preparation process, the compounds of the general formula I are obtained through a series of reactions such as SN2 reaction, protection, coupling reaction, deprotection, condensation reaction and the like.
Carboxylation of Alkenyl Boronic Acids and Alkenyl Boronic Acid Pinacol Esters with CO2 Catalyzed by Cuprous Halide
Hong, Junting,Nayal, Onkar S.,Mo, Fanyang
supporting information, p. 2813 - 2818 (2020/05/16)
A cuprous halide catalysed carboxylation of alkenyl boronic acids and alkenyl boronic acid pinacol esters under CO2, affording the corresponding α, β-unsaturated carboxylic acids in good yield, has been developed. The potassium (E)-trifluoro(styryl)borate is also compatible with this reaction. This simple and efficient copper(I) catalytic system showed good functional group tolerance.
Application of fumaric acid monoethyl ester silver salt in preventing novel coronavirus infections
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Paragraph 0022, (2020/06/09)
The invention discloses application of fumaric acid monoethyl ester silver salt in preventing novel coronavirus infections. The application comprises the following steps: adding 1000g of fumaric acidmonoethyl ester into a reaction bottle of 5L, adding 3Kg of pure water, adding 100g of nano silver oxide while stirring, performing a stirring reaction for 9 hours, filtering the reaction liquid to remove impurities, performing vacuum distillation to spin off moisture at 60 DEG C, adding 5Kg of ethanol, performing stirring crystallization for 4.5 hours, performing filtering, collecting a solid, and performing vacuum drying on the obtained solid for 6 hours at 75 DEG C, so as to obtain the fumaric acid monoethyl ester silver salt. The fumaric acid monoethyl ester silver salt is applied to treatment and prevention on various coronaviruses. Experiments show that with a concentration of 500[mu] g/mL, a fumaric acid monoethyl ester silver salt dissolved solution has an inhibition rate of 99.9%upon coronavirus main protease, a corresponding zinc salt dissolved solution and a silver salt dissolved solution of the fumaric acid monoethyl ester silver salt have inhibition rates of 99.9% and 99.7% upon the coronavirus main protease respectively, and the effects are remarkable.