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Synthesis of p -coumaroylquinic acids and analysis of their interconversion

2017; Elsevier BV; Volume: 28; Issue: 3 Linguagem: Inglês

10.1016/j.tetasy.2017.01.015

1362-511X

Anggy Lusanna Gutiérrez Ortiz, Federico Berti, Luciano Navarini, Ângelo Filipe Almeida Monteiro, Marina Resmini, Cristina Forzato,

Fermentation and Sensory Analysis

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.