Methyl chavicol: Chemical aspects and therapeutic potential
Methyl chavicol: Chemical aspects and therapeutic potential
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DOI: https://doi.org/10.22533/at.ed.1594672409076
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Palavras-chave: Metil-chavicol. Aspectos químicos. Potencial terapêutico.
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Keywords: Methyl chavicol. Chemical aspects. Therapeutic potential.
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Abstract: Methyl chavicol (MC), also known as estragole and p-allylanisole, is a phenylpropanoid found in essential oils and possesses various biological properties. This study was based on a literature review of scientific articles and other publications on the topic. Sources were accessed from recognized databases such as Google Scholar, Scielo, and PubMed, among others. The biosynthesis of MC occurs through the shikimic acid metabolic pathway, involving a series of reactions (decarboxylation, aromatization, and amination) that lead to phenylalanine, cinnamic acid, and the isomers atenol and MC. The synthesis of MC involves the formation of the aryl-allyl C-C bond from phenol, using aryl halides via Stille reaction, aryl Grignard and aryl zinc derivatives, and arylboronic substances. Structural modifications can be performed using the concepts of bioisosterism and classical isosterism. For example, treatment with meta-chloroperbenzoic acid leads to the synthesis of 2-[(4-methoxyphenyl)methyl]oxirane (2), which, after reacting with acetic anhydride, yields the derivative 3-(4-methoxyphenyl)propane-1,2-diol (8). The therapeutic potential of MC is related to its insecticidal, local anesthetic, anti-inflammatory, antimicrobial, antioxidant, pancreatic lipase inhibitory, and antiproliferative properties. However, its hepatocarcinogenic potential and the carcinogenicity linked to genotoxic metabolites are also highlighted. Based on these findings, MC and its derivatives may represent a therapeutic potential for treating conditions related to inflammatory, oxidative, metabolic, and infectious processes.
- Bruna Celeida Silva Santos
- Ângelo Márcio Leite Denadai
- Ana Lúcia Santos de Matos Araújo
- ORLANDO VIEIRA DE SOUSA