Development of C-Arylcalix[4]resorcinarenes and C-Arylcalix[4]pyrogallolarenes as Antioxidant and UV-B Protector

Autor: Jumina Jumina, Dwi Siswanta, Abdul Karim Zulkarnain, Sugeng Triono, Priatmoko Priatmoko, Emmy Yuanita, Nela Fatmasari, Ikhsan Nursalim
Jazyk: angličtina
Rok vydání: 2019
Předmět:
Zdroj: Indonesian Journal of Chemistry, Vol 19, Iss 2, Pp 273-284 (2019)
Druh dokumentu: article
ISSN: 1411-9420
2460-1578
DOI: 10.22146/ijc.26868
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.
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