Relationship structure-antioxidant activity of hindered phenolic compounds

X. C. Weng; Y. Huang

doi:10.3989/gya.0225141

Autores/as

X. C. Weng School of Life Sciences, Shanghai University
Y. Huang School of Life Sciences, Shanghai University

DOI:

https://doi.org/10.3989/gya.0225141

Palabras clave:

DPPH, Efecto sinérgico estérico, Fenoles impedidos estéricamente, Rancimat, Relación estructura-actividad

Resumen

La relación entre estructura y la actividad antioxidante de 21 compuestos fenólicos con impedimentos estéricos fue investigado mediante ensayos con Rancimat y DPPH·. El 3-terc-butil-5-metilbenceno-1,2-diol es el antioxidante más potente en los ensayos mediante Rancimat pero no mediante ensayos con DPPH·, porque sus dos grupos hidroxilo tienen una fuerte sinergia estérica. El 2,6-Di-terc-butil-4-hidroxi-metil-fenol mostró una actividad antioxidante tan fuerte como el 2,6-di-ter-butil-4-metoxifenol en ensayos con manteca de cerdo. El 2,6-di-terc-butil-4-hidroxi-metilfenol también mostró una actividad más fuerte que el 2-terc-butil-4-metoxifenol. El grupo metileno del 2,6-di-ter-butil-4-hidroxi-metilfenol puede suministrar átomos de hidrógeno y activar radicales libres como lo hace un grupo hidroxilo fenólico porque se activa en gran medida tanto por anillo aromático como por el grupo hidroxilo. Cinco factores afectan a la actividad antioxidante de los compuestos fenólicos: cómo de estable son los radicales libres de los compuestos fenólicos después de suministrar átomos de hidrógeno; cuántos átomos de hidrógeno pueden proporcionar cada uno de los compuestos fenólicos; la rapidez con la que los compuestos fenólicos donen átomos de hidrógeno; la facilidad con la que los radicales libres de los compuestos fenólicos pueden combinarse con los radicales libres más activos, y si es o no un nuevo antioxidante el que se puede formar después de que el compuesto fenólico done los átomos de hidrógeno.

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Citas

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