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On the synthesis of hypericin by oxidative trimethylemodin anthrone and emodin anthrone dimerization: Isohypericin

Zur Synthese von Hypericin durch oxidative Dimerisierung von Trimethylemodinanthron und Emodinanthron: Isohypericin

  • Organische Chemie Und Biochemie
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Summary

The base catalyzed oxidative dimerization of emodin anthrone exclusively yields hypericin. However, on oxidative dimerization of trimethylemodinanthrone a mixture of hexamethylhypericin and hexamethylisohypericin was obtained. Chromatographic separation of the hexabenzoyl derivatives was achieved, and by saponification about equal amounts of hypericin and isohypericrin were produced. Isohypericin could be characterized for the first time by its spectroscopic data and its protonation and deprotonationpK a andpK *a values.

Zusammenfassung

Die basenkatalysierte oxidative Dimerisierung von Emodinanthron liefert ausschließlich Hypericin. Oxidative Dimerisierung von Trimethylemodinanthron ergibt jedoch ein Gemisch von Hexamethylhypericin und Hexamethylisohypericin. Die Hexabenzoylderivate wurden chromatographisch getrennt, und Hypericin und Isohypericin konnten aus diesen Derivaten durch Verseifung freigesetzt werden. Isohypercin konnte erstmals durch seine spektroskopischen Daten und seine Protonierungs- und Deprotonierungs-pK aundpK *a -Werte charakterisiert werden.

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Authors and Affiliations

  1. Institut für Chemie, Johannes-Kepler-Universität Linz, A-4040, Linz, Austria

    Heinz Falk & Gerhard Schoppel

Authors
  1. Heinz Falk
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  2. Gerhard Schoppel
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Falk, H., Schoppel, G. On the synthesis of hypericin by oxidative trimethylemodin anthrone and emodin anthrone dimerization: Isohypericin. Monatsh Chem 123, 931–938 (1992). https://doi.org/10.1007/BF00811548

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  • DOI: https://doi.org/10.1007/BF00811548

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