Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Synthesis of 2′,3′,4,4′,6′-Pentahydroxychalcone, an Aglycone of Carthamin, and Its Isomerization into 4′,5,6,7- and 4′,5,7,8-Tetrahydroxyflavanone, Carthamidin and Isocarthamidin
Heitaro ObaraJun-ichi OnoderaYuji KuriharaFumitada Yamamoto
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1978 Volume 51 Issue 12 Pages 3627-3630


2′,3′,4,4′,6′-Pentahydroxychalcone (4), an aglycone of carthamin, was synthesized by the demethoxymethylation of 2′,3′,4,4′,6′-pentakis(methoxymethoxy)chalcone prepared by the condensation of 2,3,4,6-tetrakis(methoxymethoxy)acetophenone with p-methoxymethoxybenzaldehyde. 4 was converted into 4′,5,6,7- and 4′,5,7,8-tetrahydroxyflavanone (5 and 6) by boiling with methanolic hydrochloric acid. On the basis of the comparisons of the properties of 5 and 6 with those of carthamidin (A) and isocarthamidin (B) derived from natural product, the structures originally assigned for A and B should be reversed.

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