Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on the Coloration Mechanism of Furostanol Derivatives with Ehrlich Reagent. I. On the Reaction of 3, 26-Dimethoxyfurost-5, 20-diene with Ehrlich Reagent
TENJI KONISHISHIU KIYOSAWAJUNZO SHOJI
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Keywords: ^<13>C-NMR
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1984 Volume 32 Issue 6 Pages 2111-2116

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Abstract

From the reddish reaction mixture of 3, 26-dimethoxy-furost-5, 20-diene (ψ-diosgenin dimethyl ether, 2) with Ehrlich reagent, a colorless condensation product was isolated and characterized as 3, 26-dimethoxy-23-(p-dimethylaminobenzylidenyl)-furost-5, 20-diene (3). However, a coexisting red product could not be isolated because of its instability. On treatment with dried hydrogen chloride or conc. hydrochloric acid, the colorless chloroform solution of 3 readily changed into a reddish solution, which was reversibly decolorized on addition of 3% ammonia-chloroform solution. Based on ultraviolet and carbon-13 nuclear magnetic resonance spectral analysis, the coloration mechanism of 2 with Ehrlich reagent has been inferred to be as follows. The reaction is initiated by condensation between p-dimethylaminobenzaldehyde and 2 to form 3, followed by protonation to form an iminium cation (3B) under acidic conditions.

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© The Pharmaceutical Society of Japan
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