Systematically investigation on the spectral, antioxidant and antibacterial properties of fragrant methyl benzoate esters containing electron withdrawing and electron releasing groups


Alemdar A., Tan B., Toksöz O., Kurtuluş G., Sesal C., ODABAŞ Z.

Journal of Molecular Structure, cilt.1291, 2023 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1291
  • Basım Tarihi: 2023
  • Doi Numarası: 10.1016/j.molstruc.2023.136100
  • Dergi Adı: Journal of Molecular Structure
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Anahtar Kelimeler: Antibacterial, Antioxidant, Electron-releasing, Electron-withdrawing, Methyl benzoates
  • Marmara Üniversitesi Adresli: Evet

Özet

In this study, the effects of electron-withdrawing or electron-releasing groups in methyl benzoate esters, which are widely used in the fragrance industry, on the antioxidant and antibacterial activities of the compounds were investigated. Firstly, methyl benzoates with electron-withdrawing (NO2 and Cl groups) or electron-donating groups (CH3 and OCH3 groups) in the para position, which are commercial compounds, were synthesized, and extensively studied in terms of reaction conditions, and spectral data in their instrumental analysis methods. Then, the synthesized compounds were evaluated for their antioxidant, antibacterial, and cytotoxic activities. Among them, methyl 4-nitrobenzoate exhibited the highest inhibition against Staphylococcus aureus and Pseudomonas aeruginosa. Methyl 4-methoxybenzoate was selected for cytotoxicity evaluation due to its high antioxidant activity, and while the results indicated a dose-dependent decrease in cell viability, lower concentrations may still be considered for cosmetic applications. These findings suggest that antioxidant activity and cytotoxic activity are directly related to the electron density of the molecule. Therefore, this very up-to-date research covers many implications for organic chemistry, medicinal chemistry, biotechnology, and microbiology. Therefore, the results obtained may have great potential to be applied in the cosmetic industry and could be used as exceptionally useful information on alternative raw material selection for researchers in the fragrance industry. These results also suggest that methyl benzoates have potential as lead compounds for the development of novel antioxidant, antibacterial, and cytotoxic agents, but further studies are needed to fully explore their applications in various fields.