Niobium Pentachloride as a Stoichiometric Reagent in the Sequential Transesterification-Esterification Reactions for the Synthesis of Methyl Salicylate and the Study of Its Antimicrobial Activity

Sandro Luiz Barbosa; DAVID LEE NELSON; Milton de Freitas Souza; Lucas Paconio Silva; Wallans TORRES PIO DOS SANTOS; ALEXANDRE PEREIRA WENTZ; Erenilda F. de Macedo; Rafaela C. Queiroz; Dayane B. Tada; Carolina R. Hurtado; Katia Conceição; Gabriela R. Hurtado; Fernando L. P. Pessoa; Gabriel de P. Bueno; Giuliano C. Clososki

doi:10.20944/preprints202305.0545.v1

How to cite: Barbosa, S.L.; NELSON, D.L.; Souza, M.D.F.; Silva, L.P.; SANTOS, W.T.P.D.; WENTZ, A.P.; Macedo, E.F.D.; Queiroz, R.C.; Tada, D.B.; Hurtado, C.R.; Conceição, K.; Hurtado, G.R.; Pessoa, F.L.P.; Bueno, G.D.P.; Clososki, G.C. Niobium Pentachloride as a Stoichiometric Reagent in the Sequential Transesterification-Esterification Reactions for the Synthesis of Methyl Salicylate and the Study of Its Antimicrobial Activity. Preprints 2023, 2023050545. https://doi.org/10.20944/preprints202305.0545.v1 Barbosa, S.L.; NELSON, D.L.; Souza, M.D.F.; Silva, L.P.; SANTOS, W.T.P.D.; WENTZ, A.P.; Macedo, E.F.D.; Queiroz, R.C.; Tada, D.B.; Hurtado, C.R.; Conceição, K.; Hurtado, G.R.; Pessoa, F.L.P.; Bueno, G.D.P.; Clososki, G.C. Niobium Pentachloride as a Stoichiometric Reagent in the Sequential Transesterification-Esterification Reactions for the Synthesis of Methyl Salicylate and the Study of Its Antimicrobial Activity. Preprints 2023, 2023050545. https://doi.org/10.20944/preprints202305.0545.v1

Abstract

Methyl Salicylate (MS), the principal constituent of Wintergreen oil (WO) was obtained from acetyl salicylic acid (ASA) by sequential transesterification-esterification reaction promoted by NbCl5for the first time. The reagents were added simultaneously, and the reaction process involved the transesterification and esterification reactions, which were accompanied by thin layer chromatography and gas chromatography. The conversion rate via GC was 100%, and the MS yield was 94%. A cytotoxicity of 50% and 64% for cultured S. aureus and metastatic melanoma cells, respectively, was observed for a concentration of 0.6 mg/mL, whereas no cytotoxicity for non-tumor cells was observed for this concentration, and it is considered to be the optimum concentration.

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Niobium Pentachloride as a Stoichiometric Reagent in the Sequential Transesterification-Esterification Reactions for the Synthesis of Methyl Salicylate and the Study of Its Antimicrobial Activity

Abstract

Keywords

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