Novel chemoselective de-esterification of esters of polyacetoxy aromatic acids by lipases

Candida cylindracea lipase (CCL) and porcine pancreatic lipase (PPL) have been used for deacetylation of peracetates of methyl and ethyl esters of six different polyphenolic acids in organic solvents. Exclusive de-esterification of the ester groups derived from the phenolic hydroxy and aliphatic acid over the ester group of the aromatic acid and aliphatic alcohol has been achieved affording the corresponding esters of phenolic acids in as high yields as 90-97%. The results have been corroborated with the mechanism of lipase action. (C) 1997, Elsevier Science Ltd.