• Synthetic experiments in the benzopyrone series - Part XXIV. A synthesis of isogenistein

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      https://www.ias.ac.in/article/fulltext/seca/037/04/0514-0519

    • Keywords

       

      Isoflavone; Oxazolone; Trimethoxy; Dimethyl Sulphate; Ethyl Formate

    • Abstract

       

      One of the substances occurring in soya beans has been considered by Okano and Beppu to be 5∶7∶2′-trihydroxy isoflavone (isogenistein), based on degradation studies. A compound of this structure has now been made starting from 2∶4∶6-trihydroxy-2′-methoxy phenyl benzyl ketone. Partial methylation, treatment with ethyl formate and sodium followed by demethylation yield the required isoflavone. Aluminium chloride in benzene solution is found to be a much better reagent than hydriodic acid for the above demethylation. The products of the present synthesis are found to be different from the natural compound and its derivatives. Therefore the natural compound cannot be an isoflavone of this constitution. The main degradation product, considered to be 2∶4∶6∶2′-tetrahydroxy phenyl benzyl ketone by Okano and Beppu differs considerably from a synthetic product of this constitution. Hence the natural compound cannot be a simple isoflavone or isoflavanone and should have a different structure.

    • Author Affiliations

       

      T R Seshadri1 S Varadarajan1

      1. Department of Chemistry, University of Delhi, Delhi
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