Facile Method for the Large-Scale Synthesis of 6,7,4′-Trihydroxyisoflavanone

Abstract

6,7,4′-Trihydroxyisoflavanone, the main source of which is extracted from soybeans, has been found to have diverse significant bioactivities. A large-scale, cost-effective, and facile chemical synthesis of 6,7,4′-trihydroxyisoflavanone is presented herein. Its synthesis is characterized by three steps with an overall yield of 71% and a purity or more than 99.0%. This reaction can be scaled up to multikilogram quantities, providing a solid basis for its further bioactivity studies and drug development. With this same method, 6,7,3′,4′-tetrahydroxyisoflavanone, an analog of 6,7,4′-trihydroxyisoflavanone, also can be largely prepared, indicating this modified synthetic method is potentially available for large-scale synthesis of a broad range of multihydroxyl isoflavanones.

GRAPHICAL ABSTRACT

Keywords:

• Demethylation
• deoxybenzoin
• Houben–Hoesch reaction
• isoflavanone
• large-scale synthesis

Notes

Jing Liu and Zhangyou Yang contributed equally to this work.