Collect. Czech. Chem. Commun. 2000, 65, 1609-1618

Synthesis and Acid-Catalyzed Hydrolysis of Some 3-(4-Methoxyphenyl)propyl Glucuronates

Monika Polákováa,*, Dušan Joniaka and Miloslav Ďurišb

a Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, 842 38 Bratislava, Slovakia
b Water Research Institute, Hydroanalytical Laboratories, Nábrežie L. Svobodu 5, 812 49 Bratislava, Slovakia


3-(4-Methoxyphenyl)propyl D-glucuronate, 3-(4-methoxyphenyl)propyl methyl 4-O-methyl-α-Dglucopyranosiduronate, 3-(4-methoxyphenyl)propyl 1,2,3,4-tetra-O-acetyl-α-D-glucopyranuronate and 3-(4-methoxyphenyl)propyl 1,2-(S):3,5-di-O-benzylidene-α-D-glucofuranuronate were prepared as a model substances for the ester lignin-saccharide bonds. Rates of acid-catalyzed hydrolysis of the prepared compounds in 1 M HCl in acetonitrile-water 3 : 1 at 20 °C have been measured by LC-DAD analysis and it showed the low stability of the ester bonds towards acid hydrolysis.

Keywords: Carbohydrates; Glucuronates; Esters; Hydrolysis; Reaction kinetics; Lignins; Uronates; Uronic acids.

References: 22 live references.