Fumaric acid monoethyl ester

Hou, Q. P., Grijpma, D. W. Feijen, J. (2009) Creep-resistant elastomeric networks prepared by photocrosslinking fumaric acid monoethyl ester-functionalized poly(trimethylene carbonate) o]igomeis. Acta Biomaterialia, 5, 1543-1551. Ifkovits, J. L. Burdick, J. A. (2007) Review Photopolymerizable and degradable biomaterials for tissue engineering apphcations. Tissue Engineering, 13, 2369-2385. 

The effect of systemically and/or topically administered fumaric acid monoethyl ester (ethyl fumarate) on psoriasis was studied by Dubiel and Happle (1972) in six patients. Two patients who had been treated with locally applied ointments consisting of 3% or 5% ethyl fumarate in petrolatum developed symptoms of renal toxicity. 

Building on this chemistry, the same authors developed a novel four-component reaction of p-hydroxybenzaldehyde derivatives, benzylamine derivatives, fumaric acid monoethyl ester and isonitriles in water under microwave irradiation to give natural product-like 5,5,6-fused azaspiro tricycle systems 16 as the main products [11]. This transformation can be assmned to proceed through addition of a final aza-Michael step to the previously developed Ugi/Michael domino sequence, and generates six contiguous bonds and fonr stereogenic centres, including one... 

Monoethyl fumarate Fumarlc acid, monoethyl ester (8) 2-Butened1o1c acid (E)-, nxinoethyl ester (9) (2459-05-4)... 

Condensation of fumaric acid chloride monoethyl ester 147 with aminoalcohol 146, followed by intramolecular Michael addition of the isolated amide 148, afforded the l,4-benzoxazepine-3-acetate 149. The thermodynamically favored 3,5-tram-isomers were obtained (Scheme 21) <2002BMC385, 2002BMC401, 2002JME4571>. 

Fumaric acid (pkTj = 3.09, p 2 = 4.60 at 25 °C, see Section 8.2.6.1.2) is used as an acidulant and preservative (E297) for inhibition of lactic acid fermentation in wines. Fumaric acid and its esters (especially monomethyl and monoethyl esters) may slow down the formation ofbotulinum toxin formation in canned meat and prevent the growth of moulds in bread. 

A soln. of fumaric acid diloride monoethyl ester in methylene chloride added dropwise to an ice-cooled soln. of 2-(4-phenylbutadienyl)piperidine and pyridine in methylene chloride, and stirring continued 2 hrs. at 0° tricyclic lactam. Y >70%. H. W. Gschwend, Helv. 56, 1763 (1973). 

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