The enzymatic synthesis of phenolic lipids (PLs) by transesterification of flaxseed oil with 3,4-dihydroxyphenyl acetic acid (DHPA) was investigated in solvent-free medium (SFM), using Novozym 435 from Candida antarctica as the biocatalyst. The effects of selected reaction parameters, water activity (a(w)), enzyme concentration and agitation speed, were studied and optimized. Increasing the a(w) of the reaction mixture from 0.18 to 0.38 resulted in a significant increase in the bioconversion yield from 62 to 77%. APCI-MS analysis confirmed the formation of six 3,4-dihydroxyphenyl acetoylated lipids, which were monolinolenyl, dioleyl, dilinolenyl, linoleyl linolenyl, oleyl linolenyl and oleyl linoleyl dihydroxyphenyl acetates. The highest enzymatic activity (178 nmol of PLs/g solid enzyme/min) was obtained using 40 mg of solid enzyme (400 PLU)/mL at agitation speed 150 rpm. Using the optimized conditions, the phenolic lipids showed a high relative proportion of linolenic acid (C-18:3 n-3) that increased from 57% in the flaxseed oil to 75 and 64% in the produced phenolic mono- and diacylglycerols, respectively. In addition, the synthesized phenolic lipids demonstrated a 7.2-fold lower radical scavenging activity than that of DHPA but half that of alpha-tocopherol. (C) 2012 Elsevier Ltd. All rights reserved.