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IMPROVEMENT OF CHEMICAL SYNTHESIS OF GENISTEIN ISOFLAVONE

Authors: Vladimir Gennadievich Dudarev; Vadim Maksimovich Raevsky; Olga Yuryevna Strelova; Anna Anatolyevna Starodubtseva;

IMPROVEMENT OF CHEMICAL SYNTHESIS OF GENISTEIN ISOFLAVONE

Abstract

Genistein (4',5,7-trihydroxyisophlavone) is found in representatives of the family Fabaceae and plays an important role in the regulation of plant cells. Genistein shows a wide range of biological activity in vivo and in vitro experiments: estrogenic, anticancer, antidiabetic, immunostimulating, antioxidant, radioprotective. The aim of the work was to modernize and study in more detail the chemical synthesis of genistein using the "deoxybenzoin" scheme. In the Houben-Höesch reaction between phloroglucinol and (4-hydroxyphenyl)acetonitrile, the diethyl ether can be substituted for the less flammable 1,4-dioxane with increased yield. As a catalyst for this reaction, instead of zinc (II) chloride, it is more convenient to use boron trifluoride etherate in the proportion 0.5 mol/mol of genistein. The study of the products of the reaction of deoxybenzoin with the Vilsmeier reagent showed that in the absence of boron trifluoride etherate, the reaction proceeds non-selectively and a mixture of genistein, 6-formyl- and 8-formylgenistein is formed. Increasing excess boron trifruoride etherate leads to substantial increase in genistein yield. The obtained results can be used in the production and quality control of the pharmaceutical substance genistein.

Keywords

Wilsmeier-Haak reaction, реакция Вильсмайера-Хаака, (4-гидроксифенил)ацетонитрил, генистеин, реакция Губена-Хёша, floroglucinol, Guben-Hoesch reaction, дезоксибензоин, pharmaceutical substance, genistein, deoxybenzoin, фармацевтическая субстанция, (4-hydroxyphenyl) acetonitrile, флороглюцин

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selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
0
Average
Average
Average
gold
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