Production and properties of chlorogenic acid lipophilic esters

Abstract

AbstractChlorogenic acid is a dietary polyphenol with important bioactivities. However, its high hydrophilicity prevents its applications as an antioxidant for lipid protection in a complex matrix such as food. Grafting an aliphatic chain onto chlorogenic acid, so‐called lipophilisation, via lipase‐catalysed esterification represents an efficient means of increasing its lipophilicity. A series of alkyl esters with various chain lengths were produced and used to explore the structure‐antioxidant activity relationship of amphiphilic antioxidants. Data obtained from complex systems (oil‐in‐water emulsion and cell culture) concluded that short or medium chain lengths enhance the antioxidant activity while longer chains tend to decrease the antioxidant ability of chlorogenic acid. This phenomenon remains to be fully explained. Acyl esters, in which the carboxylic acid group remains free were also produced and were shown to be interesting antioxidant candidates as well as useful tools for the understanding of antioxidant activities.