Chemical Structure and Sweet Taste of Isocoumarin and Related Compounds. IX

Abstract

Structural modification of the phenyl moiety (A moiety) of β-(3-hydroxy-4-methoxyphenyl) ethylbenzene (I), which constitute an essential part of phyllodulcin molecules, was attempted to make the relationship between structure and sweet taste clearer. Twenty-four derivatives of A moiety of I were synthesized, the compound (II, IV, V, VI, X, XXII, XXIII, and XXVI) revealed sweet taste and the other compounds were tasteless. On the basis of these data, the taste of these compounds were discussed in connection with the stereochemical hindrance effect of substituents.