Hesperidin dihydrochalcone

Fig. 8.5. Relative sweetening strength of some sweeteners as a function of the saccharose concentration ( neo-hesperidin dihydrochalcone, A saccharin, o aspartame, acesulfame K) (according to Bar et al, 1990)...

A sweet compound can be obtained from the neutral-tasting hesperidin of oranges by first converting hesperidin to another neutraltasting compound, hesperidin dihydrochalcone. The latter can then be hydrolyzed, by acidic or enzymatic catalysis, to remove the rhamnose residue, yielding hesperidin dihydrochalcone glucoside, which is sweet. The use of dihydrochalcones as sweeteners is discussed in Section 8.8.11. 

Although the search for enzymes to convert flavanone glycosides to dihydrochalcones has not been successful (195) and the chemical conversion is facile (193, 196), several possibilities for enzymatic modification exist besides conversion of hesperidin to hesperetin-7-glucoside. Conversion of naringin (or its dihydrochalcone) to neohesperidin (or its dihydrochalcone) by enzymatic hydroxylation and chemical methylation and enzymatic rhamnosylation of hesperetin-7-glucoside or its dihydrochalcone at the 2 position (197) would yield neohesperidin dihydrochalcone. 

Suarez J, Herrera MD, Marhuenda E (1998) In vitro scavenger and antioxidant properties of hesperidin and neohesperidin dihydrochalcone. Phytomedicine 5 469... 

---