Synthesis and Taste of Some Analogs of Neohesperidin Dihydrochalcone

Abstract

The following ten new analogs of neohesperidin dihydrochalcone (DHC) (I) were synthesized: Hesperetin DHC-4′-ゲ-l-quinovopyranoside (XXVII), hesperetin DHC-4′-(ケ-l-quinovopyranosyl-(1 → 2)-ゲ-d-glucoside) (XXVIII), hesperetin DHC-4′-(ゲ-l-quinovopyranosyl-(1 → 2)-ゲ-d-glucoside) (XXIX), hesperetin DHC-4′-(ケ-l-quinovopyranosyl-(1 → 2)-ゲ-d-galaetoside) (XXX), hesperetin DHC-4′-(ゲ-l-quinovopyranosyl-(1 → 2)-ゲ-d-galactoside) (XXXI), hesperetin DHC-4′-(ケ-l-rhamnopyranosyl-(1 → 2)-ゲ-d-galactoside) (XXXII), hesperetin DHC-4′-(ケ-l-mannopyranosyl-(1 → 2)-ゲ-d-glucotide) (XXXIII), hesperetin DHC-4′-(ケ-l-mannopyranosyl-(1 → 2)-ゲ-d-galactoside) (XXXIV), hesperetin DHC-4′-(ケ-d-mannopyranosyl-(1 → 2)-ゲ-d-glucoside) (XXXV), and hesperetin DHC-4′-(ゲ-d-arabinopyranosyl-(1 → 2)-ゲ-d-glucoside) (XXXVI). The compounds XXVII, XXVIII, XXX and XXXII are 1.97, 3.4, 3.4 and 10.2 times sweeter than saccharin, respectively. From the organoleptic data, it was concluded that in the molecule I, methyl group and gauche conformation of vicinal glycol group at carbons 2 and 3 of l-rhamnose unit, and ケ1 → 2 linkage in rhamnosyl glucose are important requirements for the elicitation of intense sweet taste.