Involvement of reactive oxygen species in the oleoylethanolamide effects and its pyrazonilic analogue in melanoma cells

Lipase-Mediated Synthesis of Oleoyl Ethanolamide Starting from High-Oleic Sunflower Oil Soapstock

“…The known synthetic protocols compared to the procedure herein described are depicted in Scheme : two model chemical reactions, i.e., the classical synthesis using oleic acid chloride and ethanolamine (a), the aminolysis of methyl oleate (b), and the reference biocatalytic synthesis (c), employed as a starting point of this work …”

“…Green Metrics of the Process and Comparison with Known Routes. The known synthetic protocols compared to the procedure herein described are depicted in Scheme 2: two model chemical reactions, i.e., the classical synthesis using oleic acid chloride and ethanolamine (a), 48 the aminolysis of methyl oleate (b), 49 and the reference biocatalytic synthesis (c), employed as a starting point of this work. 13 The values of the simplified environmental factor (sE-factor) of the four processes, calculated under the hypothesis of complete recycling of reaction and postreaction solvents and water according to the formula suggested by Roschangar et al 50 (see Supporting Information for the details, Table S5), are reported in Table 2.…”

“…Quite convenient is the conversion of oleic acid into the corresponding methyl ester by Fischer esterification, followed by aminolysis (Scheme 2, route b), 49 in spite of the use of rather harsh reaction conditions to promote the second step of the procedure, with a large excess of ethanolamine, heating the reaction mixture in acetonitrile for a prolonged reaction time (24 h). Amide 1 required a purification step by column chromatography, but only analytical rather than isolation yield was reported in the text.…”