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Molecules 2012, 17(1), 556-570; doi:10.3390/molecules17010556

Synthesis and DPPH Radical Scavenging Activity of Prenylated Phenol Derivatives

1
Departamento de Química, Universidad Técnica Federico Santa María, Av. España N° 1680, Valparaíso, 2390123, Chile
2
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 / Revised: 27 December 2011 / Accepted: 4 January 2012 / Published: 6 January 2012
(This article belongs to the Section Organic Synthesis)
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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 prenylated phenols; electrophilic aromatic substitution; radical scavenging activity
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MDPI and ACS Style

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.

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