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Synthesis and DPPH Radical Scavenging Activity of Prenylated Phenol Derivatives
Departamento de Química, Universidad Técnica Federico Santa María, Av. España N° 1680, Valparaíso, 2390123, Chile
Departamento de Ciencias Químicas, Universidad Andrés Bello, Campus Viña del Mar, Los Fresnos N 52, Viña del Mar, 2561156, Chile
* Author to whom correspondence should be addressed.
Received: 2 December 2011; in revised form: 27 December 2011 / Accepted: 4 January 2012 / Published: 6 January 2012
Abstract: 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™.
Keywords: prenylated phenols; electrophilic aromatic substitution; radical scavenging activity
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Osorio, M.; Aravena, J.; Vergara, A.; Taborga, L.; Baeza, E.; Catalán, K.; González, C.; Carvajal, M.; Carrasco, H.; Espinoza, L. Synthesis and DPPH Radical Scavenging Activity of Prenylated Phenol Derivatives. Molecules 2012, 17, 556-570.
Osorio M, Aravena J, Vergara A, Taborga L, Baeza E, Catalán K, González C, Carvajal M, Carrasco H, Espinoza L. Synthesis and DPPH Radical Scavenging Activity of Prenylated Phenol Derivatives. Molecules. 2012; 17(1):556-570.
Osorio, Mauricio; Aravena, Jacqueline; Vergara, Alejandra; Taborga, Lautaro; Baeza, Evelyn; Catalán, Karen; González, Cesar; Carvajal, Marcela; Carrasco, Héctor; Espinoza, Luis. 2012. "Synthesis and DPPH Radical Scavenging Activity of Prenylated Phenol Derivatives." Molecules 17, no. 1: 556-570.