Dihydrochalcone

Dihydrochalcone (DHC) is the organic compound with the formula C₆H₅C(O)(CH₂)₂C₆H₅. It is the reduced derivative of chalcone (C₆H₅C(O)(CH)₂C₆H₅). It is a white solid that is soluble in many organic solvents. Dihydrochalcone per se is often minor significance, but some derivatives occur in nature and have attracted attention as drugs.

The formation of dihydrochalcones removes the conjugation between the two ring systems (via the ketone) when the double bond is abolished. This causes the visible color of the chalcones to disappear in their dihydrochalcone derivatives.

Natural dihydrochalcones

• Aspalathin, a C-linked dihydrochalcone glucoside found in rooibos, a common herbal tea
• Naringin dihydrochalcone, an artificial sweetener derived from naringin
• Neohesperidin dihydrochalcone, an artificial sweetener derived from citrus
• Nothofagin, a C-linked phloretin glucoside found in rooibos
• Phloretin
• Isosalipurpurin

Dihydrochalcones (3′,5′-dihydroxy-2′,4′,6′-trimethoxydihydrochalcone (methyl linderone) and 2′-hydroxy-3′,4′,5′,6′-tetramethoxydihydrochalcone (dihydrokanakugiol) can be found in twigs of Lindera lucida.

Uses

A known use of dihydrochalcone is in the synthesis of 3-phenylindene [1961-97-3]. This in-turn finds application in the synthesis of Indriline & Pyrophendane [7009-69-0].

References