Synthesis, Sunscreen, and Toxicity In Vitro Test of C-Styrylcalix[4]resorcinaryl Octacinnamate and C-Phenylcalix[4]resorcinaryl Dodecacinnamate

Budiana I Gusti Made Ngurah(1*), Paulus Taek(2)

(1) Department of Chemistry, Faculty of Education, Universitas Nusa Cendana, Kupang 85001, East Nusa Tenggara, Indonesia
(2) Department of Biology, Faculty of Education, Universitas Nusa Cendana, Kupang 85001, East Nusa Tenggara, Indonesia
(*) Corresponding Author


The need for qualified sunscreen materials has increased from year to year. This prompt researchers to find new sunscreen ingredients that have good activity. In this study, new C-styrylcalix[4]resorcinaryl octacinnamate 1 and C-phenylcalix[4]resorcinaryl dodecacinnamate 2 have been synthesized via esterification reaction. The target molecules were characterized by FTIR, 1H-NMR and LC-MS spectrometers. The sunscreen activity was evaluated using an ultraviolet spectrophotometer and the cytotoxicity assay was tested on kidney Vero cells using the cell culture method. Compound 1 was obtained as light brown solid in 68% yield with the melting point of 247 °C. Compound 2 was obtained as light yellow solid in 69% yield with melting point of 268°C. The sunscreen test shows that 1 and 2 can absorb UV-B radiation with the SPF values of 67.45 and 70.85, respectively. The cytotoxicity assay shows that the IC50 values of 1, 2, and parasol are 1468.2, 676.1 and 758.7 μg/mL, respectively. Based on the sunscreen activity test and toxicity assay, it can be said that calix[4]resorcinarenes 1 and 2 have potential to be developed as sunscreen ingredients.


synthesis; sunscreen; toxicity; esterification

Full Text:

Full Text PDF


[1] World Health Organization, 2017, Radiation: Ultraviolet (UV) Radiation and Skin Cancer, World Health Organization, Geneva, Switzerland.

[2] Le Lann, K., Surget, G., Couteau, C., Coiffard, L., Cérantola, S., Gaillard, F., Larnicol, M., Zubia, M., Guérard, F., Poupart, N., and Stiger-Pouvreau, V., 2016, Sunscreen, antioxidant, and bactericide capacities of phlorotannins from the brown macroalga Halidrys siliquosa, J. Appl. Phycol., 28 (6), 3547–3549.

[3] Saewan, H., and Jimtaisong, A., 2013, Photoprotection of natural flavonoids, J. Appl. Pharm. Sci., 3 (9), 129–141.

[4] Indrayani, A.W., Martodihardjo, S., Soenardi, S., Jumina, J., Ngurah, B.I.G.M., and Mustofa, M., 2017, Preparation and In-Vitro characterization of self-nano emulsifying system of C-phenylcalix-[4]-resorcinaryl octacinnamate and C-methylcalix-[4]resorcinaryl octabenzoate as ultraviolet absorbers, Bali Med. J., 6 (3), 569–577.

[5] Veisani, Y., Jenabi, E., Khazaei, S., and Nematollahi, S., 2018, Global incidence and mortality rates in pancreatic cancer and the association with the Human Development Index: Decomposition approach, Public Health, 156, 87–89.

[6] Zaar, O., Gillstedt, M., Lindelöf, B., Wennberg-Larkö, A.M., and Paoli, J., 2016, Merkel cell carcinoma incidence is increasing in Sweden, J. Eur. Acad. Dermatol. Venereol., 30 (10), 1708–1713.

[7] Cives, M., Mannavola, F., Lospalluti, L., Sergi, M.C., Cazzato, G., Filoni, E., Cavallo, F., Giudice, G., Stucci, L.S., Porta, C., and Tucci, M., 2020, Non-melanoma skin cancers: Biological and clinical features, Int. J. Mol. Sci., 21 (15), 5394.

[8] Zulkarnain, A.K., Susanti, M., and Lathifa, A.N., 2013, The physical stability of lotion o/w and w/o from Phaleria macrocarpa fruit extract as sunscreen and primary irritation test on rabbit, Maj. Obat Trad., 18 (3), 141–144.

[9] Manaia, E.B., Kaminski, R.C.K., Corrêa, M.A., and Chiavacci, L.A., 2013, Inorganic UV filters, Braz. J. Pharm. Sci., 49 (2), 201–209.

[10] Chawla, H.M., Pant, N., Kumar, S., Mrig, S., Srivastava, B., Kumar, N., and Black, D.S., 2011, Synthesis and evaluation of novel tetraproxycalix[4]arene enones and cinnamates for protection from ultraviolet radiation, J. Photochem. Photobiol., B, 105 (1), 25–33.

[11] Indrayani, A.W., Jawi, I.I., Artini, I.G.A., Sucindra, N.W., Martodihardjo, S., Radiono, S., Jumina, J., Ngurah, B.I.G.M., Arimurni, D.A., Wahyudi, M.D.P., Chabib, L., and Mustofa, M., 2020, Acute toxicity profile and Sun Protection Factor (SPF) nanoemulgel combination of C-phenylcalix[4] resorcinaryl octacinnamate, C-methylcalix[4] resorcinaryl octabenzoate, and quercetin in vitro and in vivo, Bali Med. J., 9 (1), 246–248.

[12] Brenner, M., and Hearing, V.J., 2008, The protective role of melanin against UV damage in human skin, Photochem. Photobiol., 84 (3), 539–549.

[13] Khan, M.A., and Engla, G., 2012, Comparative studies on sun protection factor of some sunscreen formulations used in cosmetics, Res. J. Top. Cosmet. Sci., 3 (2), 34–36.

[14] Luangpraditkun, K., Charoensit, P., Grandmottet, F., Viennet, C., and Viyoch, J., 2020, Photoprotective potential of the natural artocarpin against in vitro UVB-induced apoptosis, Oxid. Med. Cell. Longevity, 2020, 1042451.

[15] Ngurah, B.I.G.M., Jumina, J., Anwar, C., and Mustofa, M., 2017, Synthesis and in vitro evaluation of C-methylcalix-[4]resorcinaryl octacinnamate and C-methylcalix[4]resorcinaryl octabenzoate as the sunscreen, Indones. J. Chem., 17 (1), 63–70.

[16] Mercurio, D.G., Wagemaker, T.A.L., Alves, V.M., Benevenuto, C.G., Gaspar, L.R., and Maia Campos, P.M.B.G., 2015, In vivo photoprotective effects of cosmetic formulations containing UV filters, vitamins, Ginkgo biloba and red algae extracts, J. Photochem. Photobiol., B, 153, 121–126.

[17] Matsui, K., Nazifi, E., Hirai, Y., Wada, N., Matsugo, S., and Sakamoto, T., 2012, The cyanobacterial UV-absorbing pigment scytonemin displays radical-scavenging activity, J. Gen. Appl. Microbiol., 58 (2), 137–144.

[18] Wong, C., and Currie, J., 2001, Teaching with CAChe Molecular Modeling in Chemistry, Fujitsu Limited, Tokyo, Japan.

[19] Ngurah, B.I.G.M., and Yuliani, N.N., 2020, Synthesis of resorcinic acid and its Staphylococcus aureus antibacterial activity, Moroccan J. Chem., 8 (S1), 38–43.

[20] Freshney, R.I., and Freshney, M.G., 1996, Culture of Immortalized Cells, John Wiley & Sons Inc., New Jersey, 79–82.


Article Metrics

Abstract views : 1659 | views : 834

Copyright (c) 2022 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.


Indonesian Journal of Chemistry (ISSN 1411-9420 / 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Analytics View The Statistics of Indones. J. Chem.