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Synthesis of p-coumaroylquinic acids and analysis of their interconversion |
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| Authors: | Anggy Lusanna Gutiérrez Ortiz Federico Berti Luciano Navarini Angelo Monteiro Marina Resmini Cristina Forzato |
| Institution: | 1. Dipartimento di Scienze Chimiche e Farmaceutiche, Università di Trieste, via L. Giorgieri 1, 34127 Trieste, Italy;2. illycaffè S.p.A., via Flavia 143, 34100 Trieste, Italy;3. School of Biological and Chemical Sciences, Queen Mary University of London, Mile End Road, London E1 4NS, United Kingdom |
| Abstract: | The synthesis of four isomers of p-coumaroylquinic acids was performed by esterification of p-acetylcoumaroylchloride with a suitably protected (?)-quinic acid. All isomers have been characterized by means of NMR spectroscopy and circular dichroism. Acyl migration was observed in the synthesis of 3-O-p-coumaroylquinic acid and 4-O-p-coumaroylquinic acid. Calculations on the most stable conformations of all isomers have also been performed to explain the acyl migration observed during the synthesis procedure. |
| Keywords: | Corresponding author Tel : +39 0405583921 |
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