Chromogenic Reactions of Steroids with Strong Acids. V. Products in the Kober Reaction of Steroidal Estrogens

概要

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Formation and chemical structures of some products were studied in the Kober color reactions of estradiol 3-methyl ether (I) and of estrone methyl ether (II). After heating I or II with 78% (w/w) sulfuric acid at 100°for about half-hour, extraction of the reaction-mixture with benzene left the Kober-pigment in the acidic layer, which was collected in a reddish purple regin adn was instable in a neutral or alkaline aqueous solution. In this reaction, were produced 3-methyoxy-17ξ-methyl-8ξ, 9ξ, 13ξ, 14ξ-18 norestra-1,3,5(10)-triene (III), 3'-methyl-7-methoxy-1,2-cyclopenteno-9,10-dihydrophenanthrene (IV), 3'-methyl-7-methoxy-1,2-cyclopentenophenanthrene (V), 3-methoxy-17ξ-methyl-13ξ, 14ξ-18-norestra-1,3,5(10), 8-tetraene (VI), and 3-methoxy-17ξ-methyl-13ξ, 14ξ-18-norestra-1,3,5(10), 6,8-pentaene (VII) from I. The same reaction of II gave these compounds (III-VII) and the new products, methyl 3'-methyl-7-methoxy-1,2-cyclopenteno-9,10-dihydrophenanthrene-6-sulfonate (VIII) and 3'-methyl-7-methoxy-1,2-cyclopentadieno-9,10-dihydrophenanthrene (IX).
公益社団法人日本薬学会の論文
1973-08-25