Synthesis and In Vitro Evaluation of C-methylcalix[4]resorcinaryl octacinnamate and C-methylcalix[4]resorcinaryl octabenzoate as the Sunscreen

https://doi.org/10.22146/ijc.23575

Budiana I Gusti M. Ngurah(1*), Jumina Jumina(2), Chairil Anwar(3), Sunardi Sunardi(4), Mustofa Mustofa(5)

(1) Department of Chemistry, Faculty of Education and Teacher Training, Universitas Nusa Cendana, Jl. Soeharto No. 72, Kupang 85001
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara PO BOX BLS 21 Yogyakarta 55281
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara PO BOX BLS 21 Yogyakarta 55281
(4) Faculty of Medicine, Universitas Gadjah Mada, Yogyakarta 55281
(5) Faculty of Medicine, Universitas Gadjah Mada, Yogyakarta 55281
(*) Corresponding Author

Abstract


The present study was aimed to synthesize and evaluate sunscreen activity of C-methylcalix[4]resorcinaryl octacinnamate and C-methylcalix[4]resorcinaryl octabenzoate. The target compounds were synthesized in 2 steps. They were a synthesis of C-methylcalix[4]-resorcinarene via acid catalyzed the condensation of resorcinol and acetaldehyde by using HCl catalyst, followed by esterification using cinnamoyl chloride and benzoyl chloride. The characterization of the target compounds was performed by IR, 1H-NMR, 13C-NMR, and LC-MS spectrometers. The sunscreen activity test was conducted by spectroscopic method and MTT-assay. Commercial sunscreen p-amino benzoic acid (PABA) was used as a comparator to the MTT assay. The sunscreen activity test used spectroscopic showed that C-methylcalix[4]resorcinaryl octacinnamate and C-methylcalix[4]resorcinaryl octabenzoate can absorb the ultraviolet radiation between 280 and 320 nm (UV-B) with the maximum absorption at 290 nm (ε = 31.535 M-1 cm-1) and 282 nm (ε = 42.217 M-1 cm-1), respectively. The results of MTT-assay indicated that the IC50 of C-methylcalix[4]resorcinaryl octacinnamate, C-methylcalix[4]resorcinaryl octabenzoate and PABA are 12.006, 20.568 and 12.564 ppm, respectively, it means that the order of sunscreen activity is C-methylcalix-[4]resorcinaryl octacinnamate, PABA and C-methylcalix[4]resorcinaryl octabenzoate.


Keywords


synthesis; estherification; sunscreen; activity; characterization

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DOI: https://doi.org/10.22146/ijc.23575

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