Mechanism of alkaline degradation of sucrose. A study of some model compounds

Abstract

Alkaline degradation of sucrose proceeds by a slow first stage to yield reactive intermediates (perhaps glucose and fructose) which degrade rapidly to acids (predominantly lactic acid). In an attempt to determine the mechanism of the first stage of the reaction, the rates of alkaline degradation of sucrose and some model compounds have been determined unequivocally by measuring their rates of disappearance by paper or gas chromatography. Selective blocking of hydroxyl groups in sucrose by methylation, indicates that the alkaline degradation probably involves free hydroxyl groups (presumably via the derived anions) on both glucose and fructose components of sucrose. It is unlikely that the hydroxyls at C 6 of the glucose moiety or C 1? of the fructose moiety are involved.