Caffeoyl fatty acyl structural esters:enzymatic synthesis, characterization and antioxidant assessment

[Display omitted] •A novel way of lipase-catalyzed synthesis of monocaffeoyl monofatty acyl glycerols (MCMFGs) was developed.•The efficiency and yields of MCMFGs was significantly affected by the ionization and viscosity of fatty acids.•The antioxidant properties of MCMFGs decreased by the “block” effect of their fatty acyl groups on catechol group. A novel way of lipase-catalyzed synthesis of monocaffeoyl monofatty acyl glycerols (MCMFGs), caffeic acid derivatives, with improved lipophilicity was investigated. The monocaffeoyl monopalmitoyl glycerol (MCMPG), monocaffeoyl monooleoyl glycerol (MCMOG) and monocaffeoyl monolinoleoyl glycerol (MCMLG) were prepared by Lypozyme 435 catalysis between 1-MCG and fatty acids. High 1-monocafferol glycerol (1-MCG) conversion (>98.26%) and the maximum yields of MCMPG (26.26%), MCMOP (35.37%) and MCMLP (45.43%) were obtained. The MCMFGs (>95%) were purified by preparative chromatography and their structures were verified by HPLC-MS/MS and 13C NMR. The ionization and viscosity of fatty acids were major factors during the synthesis of MCMFGs. Subsequently, the antioxidant assays supported that the MCMFGs are effective antioxidants and their antioxidant properties decreased by the “block” effect of their fatty acyl groups on catechol group. This study lighted not only the application of MCMFGs in industry, but also the further design of phenol lipids.