Development of C-Arylcalix[4]resorcinarenes and C-Arylcalix[4]pyrogallolarenes as Antioxidant and UV-B Protector
Autor: | Ikhsan Nursalim, Abdul Karim Zulkarnain, Dwi Siswanta, Emmy Yuanita, Nela Fatmasari, Sugeng Triono, Jumina Jumina, Priatmoko Priatmoko |
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Přispěvatelé: | Direktorat Riset dan Pengembangan, KEMRISTEKDIKTI |
Jazyk: | angličtina |
Rok vydání: | 2019 |
Předmět: |
antioxidant
UV-B protector Vanillin calixresorcinarene calixpyrogallolarene 02 engineering and technology General Chemistry Resorcinol 010501 environmental sciences Resorcinarene 021001 nanoscience & nanotechnology 01 natural sciences Medicinal chemistry Benzaldehyde Chemistry chemistry.chemical_compound Benzoyl chloride chemistry Pyrogallol Pyridine Cinnamates 0210 nano-technology QD1-999 0105 earth and related environmental sciences |
Zdroj: | Indonesian Journal of Chemistry; Vol 19, No 2 (2019); 273-284 Indonesian Journal of Chemistry, Vol 19, Iss 2, Pp 273-284 (2019) |
ISSN: | 1411-9420 2460-1578 |
Popis: | Indonesia is rich with essential oils such as anise and clove leave oils. In respect to explore the potential utilization of these resources, it has been conducted the transformation of p-hydroxybenzaldehyde and vanillin (4-hydroxy-3-methoxy benzaldehyde) respectively derived from anise oil and clove leaves oil to a series of C-arylcalix[4]resorcinarenes and C-arylcalix[4]pyrogallolarene macrocycles. Treatment of these aldehydes with resorcinol in the presence of HCl in absolute ethanol at reflux for 8 h afforded C-4-hydroxyphenylcalix[4]resorcinarene (3a) and C-4-hydroxy-3-methoxy phenyl-calix[4]resorcinarene (3b) in good yields. When the aldehydes were treated with pyrogallol under the similar condition, the products were C-4-hydroxyphenyl calix[4]pyrogallolarene (3c) and C-4-hydroxy-3-methoxyphenylcalix[4]pyrogallolarene (3d) which were also obtained in excellent yields. Treatment of these calix[4]resorcinarenes and calix[4]pyrogallolarenes with cinnamoyl chloride and benzoyl chloride in pyridine afforded the corresponding cinnamate esters and benzoate esters in high yields. The resulted C-arylcalix-[4]resorcinarenes and C-arylcalix[4]pyrogallol arenes were subjected to antioxidant activity test using DPPH method and showed strong activity with IC50 values of 15–80 μg/mL. In terms of the synthesized calix cinnamates, the compounds showed UV-B absorption with SPF values of 15–30 at a concentration of 25 ppm which demonstrate their potential to be applied as a UV-B protector. Furthermore, these compounds were also tested for their photostability on the UV-B region and the results showed that the compounds were still unstable under irradiation for 30 min. |
Databáze: | OpenAIRE |
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