Harizal Harizal, umina umina, Tutik Dwi Wahyuningsih


Synthesis and characterization of C-4-benzyloxyphenylcalix[4]pyrogallaryl dodecabenzoat have been successfully conducted. Synthesis of target compound was carried out throught three consecutive steps comprising 1) benzylation of 4-hydroxybenzaldehyde, 2) preparation of C-4-benzyloxyphenylcalix[4]pyrogallarene cyclotetramer, and 3) O-benzoilation of C-4-benzyloxyphenylcalix[4]pyrogallarene. Additional characterizations were performed by determining electronic absorbance profile (absorbance region, lmax and e), and photostability test. Based on the results obtained, the product has the absorbance in UVC region with relatively high ε value.


Keywords: calix[4]pyrogallarene, sunscreen, benzoate, acylation

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Abis, L., Arrighi, V., Cometti, G., Dalcanale, E., & Du Vosel, A. (1991). Deuterium NMR investigation of a new class of macrocyclic columnar liquid crystal. Liquid Crystals, 9(2), 277–284.

Åhman, A., Luostarinen, M., Schalley, C. A., Nissinen, M., & Rissanen, K. (2005). Derivatisation of pyrogallarenes. European Journal of Organic Chemistry, (13), 2793–2801.

Bonsignore, S., Cometti, G., Dalcanale, E., & Du Vosel, A. (1990). New columnar liquid crystals correlation between molecular structure and mesomorphic behaviour. Liquid Crystals, 8(5), 639–649.

Chawla, H. M., Pant, N., Kumar, S., Mrig, S., Srivastava, B., Kumar, N., & Black, D. S. (2011). Synthesis and evaluation of novel tetrapropoxycalix[4]arene enones and cinnamates for protection from ultraviolet radiation. Journal of Photochemistry and Photobiology B: Biology, 105(1), 25–33.

Cometti, G., Dalcanale, E., Vosel, A. Du, & Levelut, A.-M. (1990). New bowl-shaped columnar liquid crystals. Journal of the Chemical Society, Chemical Communications, 163–165.

Cometti, G., Dalcanale, E., Vosel, A. Du, & Levelut, A. M. (1992). A new, conformationally mobile macrocyclic core for bowl-shaped columnar liquid crystals. Liquid Crystals, 11(1), 93–100.

Cotterill, A. S., Hartopp, P., Jones, G. B., Moody, C. J., Norton, C. L., O’Sullivan, N., & Swann, E. (1994). Cyclopropamitosenes, novel bioreductive anticancer agents. Synthesis of 7-methoxycyclopropamitosene and related indolequinones. Tetrahedron, 50(25), 7657–7674.

Dondoni, A., & Marra, A. (2010). Calixarene and calixresorcarene glycosides: Their synthesis and biological applications. Chemical Reviews, 110(9), 4949–4977.

Kumar, S., Chawla, S., & Zou, M. C. (2017). Calixarenes based materials for gas sensing applications: a review. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 88(3–4), 129–158.

Lijanova, I. V., Moggio, I., Arias, E., Vazquez-Garcia, R., & Martínez-García, M. (2007). Highly fluorescent dendrimers containing stilbene, and 4-styrylstilbene with resorcinarene cores: synthesis and optical properties. Journal of Nanoscience and Nanotechnology, 7(10), 3607–3614.

Maerz, A. K. (2011). Synthesis and characterization of host-guest complexes : Metal-organic nanocapsules using aryl-substituted pyrogallol[4]arenes. University of Missouri-Columbia.

Natarajan, N., Brenner, E., Sémeril, D., Matt, D., & Harrowfield, J. (2017). The Use of resorcinarene cavitands in metal-based catalysis. European Journal of Organic Chemistry, 2017(41), 6100–6113.

Ngurah, B. I. G. M., Jumina, J., Anwar, C., Sunardi, S., & Mustofa, M. (2017). Synthesis and in vitro evaluation of C-methylcalix[4]resorcinaryl octacinnamate as the sunscreen. Indonesian Journal of Chemistry, 17(1), 63.

Nimse, S. B., & Kim, T. (2013). Biological applications of functionalized calixarenes. Chemical Society Reviews, 42(1), 366–386.

Roscher, N. M., Lindemann, M. K. O., Bin Kong, S., Cho, C. G., & Jiang, P. (1994). Photodecomposition of several compounds commonly used as sunscreen agents. Journal of Photochemistry and Photobiology, A: Chemistry, 80(1–3), 417–421.

Ungnade, H. E., & Lamb, R. W. (1952). The absorption spectra of benzoic acid and esters. Journal of the American Chemical Society, 74(15), 3789–3794.


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