Synthesis of flavonoid glycosides. VIII. Structure and taste of some dihydrochalcone glycosides.

Abstract

The following ten new analogs of neohesperidin dihydrochalcone (DHC) (I) were synthesized: Hesperetin DHC-4′-β-l-glucopyranoside (II), hesperetin DHC-4′-[2-O-methyl-β-d glucopyranoside] (III), hesperetin DHC-4′-[3-O-methyl-β-d-glucopyranoside] (IV), hesperetin DHC-4′-[6-0-methyl-β-d-glucopyranoside] (V), hesperetin DHC-4′-β-d-glucopyranosiduronic acid (VI), hesperetin DHC-4′-β-maltotrioside (VII), hesperetin DHC-4′-[β-l-glucopyranosyl- (1→2)-β-d-glucopyranoside] (VIII), 3,2′,4′-trihydroxy-4-methoxydihydrochalcone-4′-[α-l- rhamnopyranosyl-(l→2)-β-d-galactopyranoside] (IX), 3,4′-dihydroxy-4-methoxydihydrochal- cone-4′-[α-l-rhamnopyranosyl-(l→2)-β-d-galactopyranoside] (X) and 4,2′,4′-trihydroxydihy- drochalcone-4′-[α-l-rhamn opyranosyl - (1→2)-β-d-galactopyranoside] (XI).Compounds II, III, IV, V, VII, VIII, IX, and X are 0.8, 2.0, 0.8, 4.0, 1.4, 0.02, 4.5 and 0.004 times as sweet as saccharin, respectively, while VI and XI are tasteless.