The primary decomposition products of the reducing hexose sugars are generally considered to be glyceraldehyde and its ketoisomer dihydroxyacetone. These two trioses can enolize in alkaline solution to give the 1,2 triose endiol, and it is through this common product that these two compounds are inter-related.Many investigators (1,6,7,11,12,13,16,17) have shown that acetol, methylglyoxal and triose-reductone are produced from glyceraldehyde, dihydroxyacetone and from the hexose sugars. Sattler and Zerban (14) have suggested that glyceraldehyde and dihydroxyacetone are intermediates in the formation of acetol methylglyoxal and triose-reductone. Likewise it has been suggested by Zerban and Sattler (18,19) and by Enders (5) that methylglyoxal, acetol and triose-reductone have a role in the darkening (browning) of hexose and triose sugars. It would appear that the pH of sugar solutions has a pronounced effect on the production of these carbonyls. It has been shown by Meyerhoff and Lohmann .(ll) and Thornton and Speck (16) that in acid solution methylglyoxal is formed from dihydroxyacetone and by Nodzu et al (11) and Prey et al (13) that acetol, and by Bauer and Teed (2) and Weygand (17) that triose-reductone are formed in alkaline solutions. These findings together with work done at this laboratory (8) suggest that browning (caramelization) of hexose and triose sugars proceed through the intermediate formation of methylglyoxal, acetol and triose-reductone depending upon the pH of the solution.This study was undertaken to obtain a better understanding of the intermediates formed in the browning of the trioses, dihydroxyacetone and glyceraldehyde, in solutions of pH 4 to 11. EXPERIMENTAL