Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Chromogenic Reactions of Steroids with Strong Acids. V. Products in the Kober Reaction of Steroidal Estrogens
木村 道也河田 明治秋山 和幸針田 和明三浦 敏明
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1973 年 21 巻 8 号 p. 1741-1746

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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).
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