title: A novel efficient and versatile route to the synthesis of 5-O-feruloylquinic acids.
abstract: A novel synthesis of 5-O-feruloylquinic acid, a polyphenolic compound found in coffee beans, and its methyl ester derivative has been optimized. The sequence involves 6 steps and is compatible with the preparation of potential human metabolites of these compounds. The key reaction is a Knoevenagel condensation of 4-hydroxy-3-methoxy-benzaldehyde and a malonate ester of quinic acid.
authors.affiliation: Nestlé Research Center, Vers Chez Les Blanc 1000, Lausanne 26, Switzerland.
authors.forename: Candice Menozzi
authors.initials: CM
authors.lastname: Smarrito
authors.forename: Caroline
authors.initials: C
authors.lastname: Munari
authors.forename: Fabien
authors.initials: F
authors.lastname: Robert
authors.forename: Denis
authors.initials: D
authors.lastname: Barron
mesh_terms: D001547:Benzaldehydes / Q000737:chemistry*; D003373:Coumaric Acids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011801:Quinic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D001547:Benzaldehydes; D003373:Coumaric Acids; D011801:Quinic Acid; C100058:vanillin