Title | : | Synthesis and High Antioxidant Activity of C-Alkyl Calix[4]resorcinarene and C-Alkyl Calix[4]pyrogallolarene Derivatives |
Author | : |
Prof. Drs. Jumina, Ph.D. (1) YEHEZKIEL STEVEN KURNIAWAN (2) RATNA SARI W (3) SRI NESSY HANDAYANI BR PURBA (4) HESTI KUSUMANINGRUM (5) Dr Priatmoko M.Sc (6) Dr. Deni Pranowo, S.Si., M.Si. (7) JEFFRY JULIANUS (9) Dr. apt. Abdul Karim Zulkarnain, M.Si.,SE. (10) dr. Eti Nurwening Sholikhah M.Kes. (11) |
Date | : | 0 2022 |
Keyword | : | Antioxidant, Alkyl Chain, Calix[4]resorcinarene, Calix[4]pyrogallolarene, In Vitro Antioxidant, Alkyl Chain, Calix[4]resorcinarene, Calix[4]pyrogallolarene, In Vitro |
Abstract | : | In the present work, a successful synthesis and high antioxidant activity of C-alkylcalix[4]resorcinarene and C-alkylcalix[4]pyrogallolarene derivatives were reported. The C-alkylcalix[4]resorcinarenes were prepared from a cyclization reaction of resorcinol and either pentanaldehyde or octanaldehyde under acidic conditions. Meanwhile, the C- alkylcalix[4]pyrogallolarenes were prepared from a cyclization reaction of pyrogallol with pentanaldehyde or octanaldehyde. Four synthesized products, i.e., nBu-CR, nHep-CR, nBu-CP, and nHep-CP, were successfully prepared in 92.4-96.4% yield. Their chemical structure was elucidated by Fourier transform infrared (FTIR), liquid chromatography-mass spectrometry (LC-MS), and proton nuclear magnetic resonance (1H-NMR) analysis. The antioxidant activity assay of these compounds was evaluated through an in vitro assay employing 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals. The DPPH assay showed that the half-maximal inhibitory concentration (IC50) values of nBu-CR, nHep-CR, nBu-CP, and nHep-CP compounds were 25.1, 22.9, 11.5, and 21.9 µg mL-1, respectively. The IC50 value of the synthesized compounds was 2.0-4.3 times lower than the positive standard of butylated hydroxytoluene (BHT, IC50 = 49.9 µg mL-1), which was remarkable. This finding demonstrates that both C- alkylcalix[4]resorcinarenes and C-alkylcalix[4]pyrogallolarenes are better antioxidant agents than BHT. The nHep-CR compound was found as the best antioxidant agent among the other compounds due to weaker intramolecular and intermolecular hydrogen bondings and a longer alkyl chain. Keywords: Antioxidant, Alkyl Chain, Calix[4]resorcinarene, Calix[4]pyrogallolarene, In Vitro |
Group of Knowledge | : | Bidang IPA Lain Yang Belum Tercantum |
Original Language | : | English |
Level | : | Internasional |
Status | : |
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SynthesisandHighAntioxidantActivityofC-Alkyl Calix[4]resorcinarene and C-Alkyl Calix[4]pyrogallolarene Derivatives.pdf
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Synthesis and High Antioxidant Activity of C-Alkyl Calix[4]resorcinarene and C-Alkyl Calix[4]pyrogallolarene Derivatives-IJP PUBLISHED.pdf
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