Relationship between lipophilicity, bitterness and structure of phenyl β-d-glucopyranosides

The relationship between lipophilicity, structure and bitterness of phenyl β-d-glucopyranosides and their methyl ether derivatives was examined quantitatively using lipophilic and STERIMOL parameters, and selected indicator variables to assess position-specific substituent effects. The results indicate that the partial lipophilicity of the methoxyl groups is different for each substituent position of the glucose moiety and that the lipophilicity of a methoxyl group at position 2 is the largest. The results also show that the bitterness of phenyl β-d-glucopyranosides is determined primarily by the presence or absence of the methoxyl group at position 2 of the glucose moiety, not by the lipophilicity of the entire molecule.