A novel efficient and versatile route to the synthesis of 5-O-feruloylquinic acids.
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.
Smarrito
Candice Menozzi
CM
Nestlé Research Center, Vers Chez Les Blanc 1000, Lausanne 26, Switzerland.
Munari
Caroline
C
Robert
Fabien
F
Barron
Denis
D
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*
D001547:Benzaldehydes; D003373:Coumaric Acids; D011801:Quinic Acid; C100058:vanillin