Ozonation of a lignin-carbohydrate complex model compound of the benzyl ether type

Evidence for the presence of lignin-carbohydrate bonds of the benzylic ether type in wood and pulps may be obtained by use of ozonation treatment to selectively degrade the lignin. It was found that the benzyl ether bond in 3- (4-hydroxy-3-methoxyphenyl)-2- (2-methoxy-phenoxy) -3-(methyl-beta-D-glucopyranosid-6-O-yl)-1-propanol was rather stable during ozonation in acetic acid-water-methanol 16:3:1 a t0 degrees C. The corresponding acid, 3,4-dihydroxy-2-(methyl-beta-D-glucopyranosid-6-O-yl)-butanoic acid, was found to be the major reaction product. The use of ozonation followed by acid hydrolysis in connection with studies of lignin-carbohydrate linkages is briefly discussed.