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Keywords:

  • Coumarins—Prunus mahaleb fruit kernels;
  • Paper chromatography—separation, identification;
  • Optical rotation— identity;
  • IR spectrophotometry—structure;
  • NMR spectroscopy—structure;
  • Mass spectroscopy—structure

Abstract

It was possible to isolate 2-glucosyloxy-4-methoxyethyl trans-cinnamate from the alcoholic extract of the defatted Prunus mahaleb L. fruit kernels. The structure of this compound was confirmed by IR, NMR, and mass spectra. Further evidence was sought through its de-ethylation into 2-glucosyloxy-4-methoxy trans-cinnamic acid which was identical in every respect with authentic material prepared synthetically. Through acetylation it afforded a tetraacetate, the structure of which was also confirmed by NMR and mass spectra. The identity of the sugar as glucose was ascertained by enzymatic and acid hydrolysis and subsequent paper chromatography in three different solvent systems.