Estudos visando a preparação e caracterização de derivados da icaridina
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Data
2023-10-18
Autores
Godoy, Emerson Santos [UNIFESP]
Orientadores
Guadagnin, Rafael Carlos [UNIFESP]
Tipo
Trabalho de conclusão de curso de graduação
Título da Revista
ISSN da Revista
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Resumo
A Icaridina, também conhecida como Picaridina ou KBR 3023 é um componente químico derivado da pimenta, encontrada nas plantas do gênero Piper L. da grande família Piperaceae. Atualmente, é utilizada comercialmente, na composição de produtos repelentes de insetos, sendo efetiva para mosquitos da família Culicidae, incluindo o Aedes aegypti, um dos principais vetores de doenças graves em países tropicais, assim como o Brasil. Este projeto visa, primeiramente, desenvolver um método prático para isolar a Icaridina pura, a partir de um produto comercial, empregando técnicas de extração líquido-líquido. Após o seu isolamento, pretende-se primeiramente realizar sua análise por técnica de cromatografia em camada delgada, e posteriormente sua caracterização por ressonância magnética nuclear de 1H e 13C, cromatografia gasosa e espectrometria de massas. Por fim, considerando que a estrutura química da Icaridina possui uma hidroxila livre, pretende-se realizar estudos visando a síntese de novos derivados alquilados da Icaridina, utilizando haletos de alquila saturados e métodos convencionais de síntese orgânica. Cabe salientar que, não foram encontrados, até o momento, nas plataformas de busca de literatura científica, derivados alquilados semelhantes aos que pretendemos sintetizar. Ao final, após revisar as análises obtidas, pode-se concluir que a eterificação dos compostos via síntese de éteres de Williamson é uma alternativa viável para obtenção de compostos eterificados, derivados de Icaridina. Esses compostos, posteriormente, em continuidade a este trabalho, poderão ter suas atividades biológicas testadas, em colaboração com outros grupos de pesquisa.
Icaridin, also known as Picaridin or KBR 3023, is an active ingredient derived from pepper found in plants of the Piper L. genus within the Piperaceae family. Currently, it is commercially used in the formulation of insect repellent products and is effective against mosquitoes of the Culicidae family, including Aedes aegypti, one of the main vectors of serious diseases in tropical countries such as Brazil. The project initially aims to develop a practical method to isolate pure Icaridin from a commercial product using liquid-liquid extraction techniques. After its isolation, it is intended to characterize it using thin-layer chromatography, 1H and 13C nuclear magnetic resonance, gas chromatography, and mass spectrometry techniques. Lastly, considering that the chemical structure of Icaridin has a free hydroxyl group, studies are planned for the synthesis of new alkylated derivatives of Icaridin using saturated alkyl halides and conventional methods of organic synthesis. It should be noted that, as of now, similar alkylated derivatives to those intended for synthesis have not been found in scientific literature search platforms. At the end, after reviewing the obtained analyses, it can be concluded that the etherification of compounds through the synthesis of Williamson ethers is a viable alternative for obtaining etherified compounds derived from Icaridin. These compounds may undergo biological activity testing in collaboration with other research groups as a continuation of this work.
Icaridin, also known as Picaridin or KBR 3023, is an active ingredient derived from pepper found in plants of the Piper L. genus within the Piperaceae family. Currently, it is commercially used in the formulation of insect repellent products and is effective against mosquitoes of the Culicidae family, including Aedes aegypti, one of the main vectors of serious diseases in tropical countries such as Brazil. The project initially aims to develop a practical method to isolate pure Icaridin from a commercial product using liquid-liquid extraction techniques. After its isolation, it is intended to characterize it using thin-layer chromatography, 1H and 13C nuclear magnetic resonance, gas chromatography, and mass spectrometry techniques. Lastly, considering that the chemical structure of Icaridin has a free hydroxyl group, studies are planned for the synthesis of new alkylated derivatives of Icaridin using saturated alkyl halides and conventional methods of organic synthesis. It should be noted that, as of now, similar alkylated derivatives to those intended for synthesis have not been found in scientific literature search platforms. At the end, after reviewing the obtained analyses, it can be concluded that the etherification of compounds through the synthesis of Williamson ethers is a viable alternative for obtaining etherified compounds derived from Icaridin. These compounds may undergo biological activity testing in collaboration with other research groups as a continuation of this work.