SÍNTESIS DE DERIVADOS DE CARVACROL Y EVALUACIÓN DE SU ACTIVIDAD ANTIMICROBIANA
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2023-06-07
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Jaén: Universidad de Jaén
Resumen
[ES] En este Trabajo Fin de Grado (TFG) se han obtenido tres derivados acilados del conocido antimicrobiano
natural carvacrol (1) mediante la reacción de acilación de Friedel-Crafts de fenoles, utilizando como agente
acilante un superácido (ácido tríflico) y cloruro de butanoilo, cuyas actividades antimicrobiana y antibiofilm
han sido evaluadas. La purificación de estos derivados se ha llevado a cabo mediante cromatografía en
columna preparativa, y su caracterización estructural mediante resonancia magnética nuclear, siendo un O-
butanoil-carvacrol (2), un C-butanoil-carvacrol (3) y un di-butanoil-carvacrol (4). Los resultados obtenidos
en la evaluación de la actividad antimicrobiana de los compuestos 1-4 muestran que el derivado 3 tiene
mayor actividad frente a bacterias de origen alimentario que el resto de los compuestos, incluida la
molécula de partida (1). Estos resultados permiten deducir algunas relaciones estructura-actividad que
pueden promover nuevas estrategias de conservación de alimentos utilizando estos derivados fenólicos,
una vez descartados sus posibles efectos citotóxicos.
[EN] In this Final Degree Project (TFG) three acylated derivatives of the well-known natural antimicrobial carvacrol (1) have been obtained by means of the Friedel-Crafts acylation reaction of phenols, using a superacid (triflic acid) and butanoyl chloride as an acylating agent, whose antimicrobial and anti-biofilm activities have been evaluated. The purification of these derivatives has been carried out by preparative column chromatography, and their structural characterization by nuclear magnetic resonance, being an O- butanoyl-carvacrol (2), a C-butanoyl-carvacrol (3) and a di-butanoyl-carvacrol (4). The results obtained in the evaluation of the antimicrobial activity of compounds 1-4 show that derivative 3 has higher activity against foodborne bacteria than the rest of the compounds, including the starting molecule (1). These results allow us to deduce some structure-activity relationships that may promote new food preservation strategies using these phenolic derivatives as biocides or preservatives in the food industry, once their possible cytotoxic effects have been discarded.
[EN] In this Final Degree Project (TFG) three acylated derivatives of the well-known natural antimicrobial carvacrol (1) have been obtained by means of the Friedel-Crafts acylation reaction of phenols, using a superacid (triflic acid) and butanoyl chloride as an acylating agent, whose antimicrobial and anti-biofilm activities have been evaluated. The purification of these derivatives has been carried out by preparative column chromatography, and their structural characterization by nuclear magnetic resonance, being an O- butanoyl-carvacrol (2), a C-butanoyl-carvacrol (3) and a di-butanoyl-carvacrol (4). The results obtained in the evaluation of the antimicrobial activity of compounds 1-4 show that derivative 3 has higher activity against foodborne bacteria than the rest of the compounds, including the starting molecule (1). These results allow us to deduce some structure-activity relationships that may promote new food preservation strategies using these phenolic derivatives as biocides or preservatives in the food industry, once their possible cytotoxic effects have been discarded.
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Química Orgánica