Synthesis of Benzoyl C-Phenylcalix[4]resorcinaryl Octaacetate and Cinnamoyl C-Phenylcalix[4]arene for UV Absorbers

https://doi.org/10.22146/ijc.21253

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

(1) Department of Chemistry, Faculty of Education and Teachers Training, University of Nusa Cendana, Jl. Adisucipto Penfui Kupang 85001, East Nusa Tenggara
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara Yogyakarta 55281
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara Yogyakarta 55281
(4) Faculty of Medicine, Universitas Gadjah Mada, Jl. Sekip Utara Yogyakarta 55281
(5) Faculty of Medicine, University of Nusa Cendana, Jl. Adisucipto Penfui Kupang 85001, East Nusa Tenggara
(*) Corresponding Author

Abstract


A new upper rim-functionalized benzoyl C-phenylcalix[4]resorcinaryl octaacetate and cinnamoyl C-phenylcalix[4]resorcinarene have been synthesized and evaluated as the absorbers for ultraviolet radiation. The benzoyl C-phenylcalix[4]resorcinaryl octaacetate was synthesized in 3 steps. They were synthesis of C-phenilcalix[4]resorcinarene via acid-catalyzed-condensation of resorcinol and benzaldehyde, followed by O-acetylation and Friedel-Craft benzoylation. The cinnamoyl C-phenylcalix[4]resorcinarene was synthesized in 4 steps. They were synthesis of C-phenilcalix[4]resorcinarene via acid-catalyzed-condensation of resorcinol and benzaldehyde, followed by O-acetylation, Friedel-Craft cinnamoylation and hydrolysis. Spectroscopic analysis (UV) showed that the target molecule absorbed the ultraviolet radiation between 200 and 400 nm with the maximum absorption at 240.50 nm (ε = 10.135 M-1 cm-1) and 243.50 nm (ε = 12.135 M-1 cm-1).

Keywords


synthesis; benzoyl; absorbers; ultraviolet

Full Text:

Full Text Pdf


References

[1] Herzog, B., Wehrle, M., and Quass, K., 2009, Photochem. Photobiol., 85 (4), 869–878.

[2] Sax, B.W., 2004, Pharm. Times, 66 (5), 48–50.

[3] Dutra, E.A., da Costa e Oliviera, D.A.G., Kedor-Hackmann, E.R.M., and Santoro, M.I.R.M., 2004, Braz. J. Pharm. Sci., 40, 381–383.

[4] World Health Organization, Sun Protection A Primary Teaching Resource http://www.who.int/phe/uv, accessed on December 23rd 2011.

[5] Korać, R.R., and Khambholja, K.M., 2011, Pharmacogn. Rev., 5 (10), 164–173.

[6] Wahyuningsih, T.W., Raharjo, T.J., and Tahir, I., 2002, Indo. J. Chem., 2 (1), 55–63.

[7] Gonzalez, H., Farbrot, A., Larkö, O., and Wennberg, A.M., 2006, Br. J. Dermatol., 154 (2), 338–339.

[8] Lago, A.F., Jimenez, P., Herrero, R., Davalos, J.Z., and Abboud, J-L.M., 2008, J. Phys. Chem. A, 112 ,3201–3202.

[9] Laurence, N., Chitry, F., Gaubert, E., and Lemaire, M., 1999, J. Inclusion Phenom. Macrocyclic Chem., 34 (2), 143–154.

[10] Jain, V.K., Pillai, S.G., and Kanaiya, P.H., 2006, J. Braz. Chem. Soc., 17 (7), 1316–1322.

[11] Tunstad, L.M., Tucker, L.A., Dalanale, E., Weiser, J., Bryant, J.A., Sherman, J.C., Helgeson, R.C., Knobler, C.B., and Cram, D.J., 1989, J. Org. Chem., 54 (6), 1305–1312.

[12] Sukwattanasinitt, M., Rojanathanes, R., Tuntulani, T., Sritana-Anant, Y., and Ruangpornvisuti, V., 2001, Tetrahedron Lett., 42 (31), 5291–5293.

[13] Chawla, H.M., Pant, N., Kumar, S., Mrig, S., Srivastava, B., Kumar, N., and Black, D.StC., 2011, J. Photochem. Photobiol., B, 105 (1), 25–33.



DOI: https://doi.org/10.22146/ijc.21253

Article Metrics

Abstract views : 2459 | views : 1791


Copyright (c) 2014 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 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web Analytics View The Statistics of Indones. J. Chem.