Abstract
Abstract Urine of rabbits and rats treated with large doses of 3-methyl-4-phenyl-3-butenamide (I) was analyzed. Four metabolic products were isolated and identified: 2-hydroxy-3-methyl-4-phenyl-3-butenamide (II), 3-methyl-4-(4'-hydroxyphenyl)-3-butenamide (III), 3-benzyl-4-hydroxy-2-butenoic acid lactone (IV), and 3-(4'-hydroxybenzyl)-4-hydroxy-2-butenoic acid lactone (V). Compound IV was shown to be a metabolic intermediate between Compounds I and V. The metabolic fate of Compound I in man was found to be the same as in rat and rabbit.
Highlights
Nuclear magnetic resonance xpcctra were recorded on a Perkin-Elmer R-10 (60 MC) spectrometer, with deuterated pyridine as solvent and tetramethylsila,ne as internal reference; chemical shifts are reported in delta, parts per million
The fraction eluted with benzene-ethyl ether, I:5 (600 ml), gave 0.5 g of 3-(4’.hydroxybenzyl)-4-hydroxy-2-butenoic acid lactone (Compound V), m.p. 125-126”; positive reaction in the
From the urine of rat and ra.bbit treated with 3-methyl-4
Summary
Ultraviolet absorption spectra were determined in methanol on a Beckman DU spectrometer, model G 2400. Infrared spectra were recorded in Nujol on a Perkin-Elmer Infracord, model 137. Nuclear magnetic resonance xpcctra were recorded on a Perkin-Elmer R-10 (60 MC) spectrometer, with deuterated pyridine as solvent and tetramethylsila,ne as internal reference; chemical shifts are reported in delta, parts per million (multiplicity, J, number of protons, and attributions are indicated in parentheses). Descending paper chromatography was performed on propylene glycol-methanol (1: 3)-impregnat,ed Whatman No 1 paper, with benzene-water-methanol (2:2: 1) as solvent and examining the chromatogram in ultraviolet light or spraying it with 3,5-dinitrobenzoic acid according to Bush [6]. The pooled urine was extracted with chloroform at pH 7.8 and the chloroform extract was washed with water, dried over anhydrous sodium sulfate, and evaporated to dryness.
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