Natural geranylhydroquinone 1 and geranyl-p-methoxyphenol 2 were prepared by Electrophilic Aromatic Substitution (EAS) reactions between geraniol and 1,4-hydroquinone or p-methoxyphenol respectively, using BF3·Et2O as a catalyst. Furthermore, natural geranylquinone 3, geranyl-1,4-dimethoxyquinone 4 and the new geranyl-4-methoxyphenyl acetate 5 were obtained by chemical transformations of 1 and 2. The compounds were evaluated for their in vitro cytotoxicity activities against cultured human cancer cells of PC-3 human prostate cancer, MCF-7 and MDA-MB-231 breast carcinoma, and Dermal Human Fibroblasts DHF. IC50 values were in the μM range.
Baeza, E., Catalán, K., Peña-Cortés, H., Espinoza, L., Villena, J., & Carrasco, H. (2012). Synthesis of geranylhydroquinone derivatives with potencial cytotoxic activity. Quimica Nova, 523-526. https://doi.org/10.1590/S0100-40422012000300015