Synthesis and DPPH Radical Scavenging Activity of Prenylated Phenol Derivatives

• Main Authors: Héctor Carrasco, Luis Espinoza, Marcela Carvajal, Cesar González, Alejandra Vergara, Lautaro Taborga, Evelyn Baeza, Karen Catalán, Mauricio Osorio, Jacqueline Aravena
• Format: Article
• Language: English
• Published: MDPI AG 2012-01-01
• Series: Molecules
• Subjects: prenylated phenols; electrophilic aromatic substitution; radical scavenging activity
• Online Access: http://www.mdpi.com/1420-3049/17/1/556/
• ISSN: 1420-3049

The synthesis of twenty six prenylated phenols derivatives is reported. These compounds were obtained under mild conditions via Electrophilic Aromatic Substitution (EAS) coupling reactions between phenol derivatives containing electron-donor subtituents and 3-methyl-2-buten-1-ol using BF3×OEt2. Dialkylations were also produced with this method. The formation of a chroman ring by intramolecular cyclization between a sp2 carbon from the prenyl group with the hydroxyl substituent in the ortho position occurred with some phenols. All the synthesized compounds were evaluated as antioxidants according to a DPPH radical scavenging activity assay. IC50 values of five synthesized compounds indicated they were as good antioxidants as Trolox™.