As modification of β-(3-hydroxy-4-methoxyphenyl) ethylbenzene (I) having the essential part of sweet phyllodulcin molecule, β-(3-methoxy-4-hydroxyphenyl) ethylbenzene (II), 3-hydroxy-4-methoxyphenylmethylbenzene (III), 3-(3-hydroxy-4-methoxyphenyl) phthalide (IV), γ-(3-hydroxy-4-methoxyphenyl) propylbenzene (V), δ-(3-hydroxy-4-methoxyphenyl) butylbenzene (VI), and β-(3-hydroxy-4-methoxyphenyl) cyclohexylethane (VII) were synthesized. II, III, IV, and VI were tasteless, while V and VII revealed a moderate sweet taste. Consequently, it seemed that not only the position of the hydroxyl and methoxyl groups but the distance between the two phenyl groups in these molecules may be important factors for the appearance of sweet taste, and π-electrns of the phenyl group in I may not be necessary for interaction with the receptor site.
