Alkylated Sesamol Derivatives as Potent Antioxidants
Metadata
Show full item recordEditorial
MDPI
Materia
Antioxidant capacity Sesamol DFT Electron transfer Hydrogen transfer
Date
2020-07-21Referencia bibliográfica
C Palheta, I., R Ferreira, L., KL Vale, J., PP Silva, O., M Herculano, A., RHM Oliveira, K., ... & S Borges, R. (2020). Alkylated Sesamol Derivatives as Potent Antioxidants. Molecules, 25(14), 3300. [doi:10.3390/molecules25143300]
Sponsorship
PROPESP/UFPA; National Council for Scientific and Technological Development (CNPq)Abstract
Sesamol is a phenolic derivative. Its antioxidant activity is low than that of Trolox and
depends on benzodioxole moiety. Thus, a molecular modification strategy through alkylation,
inspired by natural and synthetic antioxidants, was studied by molecular modeling at the DFT/B3LYP
level of theory by comparing the 6-31+G(d,p) and 6-311++G(2d,2p) basis sets. All proposed derivatives
were compared to classical related antioxidants such as Trolox, t-butylated hydroxytoluene (BHT)
and t-butylated hydroxyanisole (BHA). According to our results, molecular orbitals, single electron
or hydrogen-atom transfers, spin density distributions, and alkyl substitutions at the ortho positions
related to phenol moiety were found to be more effective than any other positions. The trimethylated
derivative was more potent than Trolox. t-Butylated derivatives were stronger than all other alkylated
derivatives and may be new alternative forms of modified antioxidants from natural products with
applications in the chemical, pharmaceutical, and food industries.