Physical Sciences and Mathematics Commons^™

Synthesis Of Hydroxycinnamate Derivatives And Characterization Of Bioactivity As Radical Scavengers And Α-Glucosidase Inhibitors, Cate Simmermaker

University of the Pacific Theses and Dissertations

Hydroxycinnamic acids (HCAs), a class of polyphenols commonly found in regularly consumed fruits and vegetables, have been investigated for efficacy as radical scavengers and glycosidase inhibitors. These compounds could mitigate the negative health effects of free radicals in oxidative stress diseases including neurodegeneration, cancer and diabetes. The HCAs investigated were caffeic acid (1), p-coumaric acid (2), ferulic acid (3), and sinapic acid (4). The compounds were derivatized with synthetically prepared amino acid esters through a four-step synthesis including protective acetylation, chlorination of the carboxylic acid, amidation, and subsequent deprotection of all applied protecting groups. The inclusion of diverse derivative groups …