SYNTHESIS AND PRELIMINARY EVALUATION OF 3,3’-DIHYDROXY-4,4’-DIMETHOXYDIBENZYLIDENEACETONE AS SUNSCREEN AND ANTIOXIDANT ACTIVE COMPOUND
Abstract
Synthesis and preliminary evaluation of 3,3’-dihydroxy-4,4’-dimethoxydibenzylidenacetone (DDB) as sunscreen and antioxidant have been successfully conducted. The compound was prepared throught acid catalyzed condensation reaction between vanillin and aceton using saturated HCl solution in glacial acetic acid. Pre-evaluation of sunscreen active compound candidate was performed by determining electronic absorbance profile, lamdamax, e, lamda c, UVA/UVB ratio, and photostability. While antioxidant activity test was performed using DPPH radical scavenger method. Based on the results obtained, the compound obtained has very good protective effect in UVA regions with high antioxidant activity.
Keyword
vanillin, dibenzylidenacetone, sunscreen, antioxidant
Downloads
Download data is not yet available.
References
[1] Parrish, J. A., Jaenicke, K. F., & Anderson, R. R. (1982). Erythema and melanogenesis action spectra of normal human skin. Photochemistry and Photobiology, 36(2), 187–191. https://doi.org/10.1111/j.1751-1097.1982.tb04362.x
[2] Dahle, J., & Kvam, E. (2003). Induction of delayed mutations and chromosomal instability in fibroblasts after UVA-, UVB-, and X-radiation. Cancer Research, 63(7), 1464–1469.
[3] Jiang, Y., Rabbi, M., Kim, M., Ke, C., Lee, W., Clark, R. L., … Marszalek, P. E. (2009). UVA generates pyrimidine dimers in DNA directly. Biophysical Journal, 96(3), 1151–1158. https://doi.org/10.1016/j.bpj.2008.10.030
[4] Fisher, G. J., Kang, S., Varani, J., Bata-Csorgo, Z., Wan, Y., Datta, S., & Voorhees, J. J. (2002). Mechanisms of photoaging and chronological skin aging. Archives of Dermatology, 138(11), 1462–1470. https://doi.org/10.1001/archderm.138.11.1462
[5] Boyd, A. S., Naylor, M., Cameron, G. S., Pearse, A. D., Gaskell, S. A., & Neldner, K. H. (1995). The effects of chronic sunscreen use on the histologic changes of dermatoheliosis. Journal of the American Academy of Dermatology, 33(6), 941–946. https://doi.org/10.1016/0190-9622(95)90284-8
[6] van Praag, M. C. G., Roza, L., Boom, B. W., Out-Luijting, C., Henegouwen, J. B. A. B., Vermeer, B. J., & Mommaas, A. M. (1993). Determination of the photoprotective efficacy of a topical sunscreen against UVB-induced DNA damage in human epidermis. Journal of Photochemistry and Photobiology, B: Biology, 19(2), 129–134. https://doi.org/10.1016/1011-1344(93)87107-X
[7] Liardet, S., Scaletta, C., Panizzon, R., Hohlfeld, P., & Laurent-Applegate, L. (2001). Protection against pyrimidine dimers, p53, and 8-hydroxy-2′-deoxyguanosine expression in ultraviolet-irradiated human skin by sunscreens: Difference between UVB + UVA and UVB alone sunscreens. Journal of Investigative Dermatology, 117(6), 1437–1441. https://doi.org/10.1046/j.0022-202x.2001.01580.x
[8] Nohynek, G. J., & Schaefer, H. (2001). Benefit and risk of organic ultraviolet filters. Regulatory Toxicology and Pharmacology, 33(3), 285–299. https://doi.org/10.1006/rtph.2001.1476
[9] Shaath, N. A. (2005). The chemistry of ultraviolet filters. In N. A. Shaath (Ed.), Sunscreens: Regulations and commercial development (third, pp. 217–238). Boca raton: Tailor & Francis Group.
[10] Kammeyer, A., & Luiten, R. M. (2015). Oxidation events and skin aging. Ageing Research Reviews, 21, 16–29. https://doi.org/10.1016/j.arr.2015.01.001
[11] Birch-Machin, M. A., & Bowman, A. (2016). Oxidative stress and ageing. British Journal of Dermatology, 175, 26–29. https://doi.org/10.1111/bjd.14906
[12] Godic, A., Poljšak, B., Adamic, M., & Dahmane, R. (2014). The role of antioxidants in skin cancer prevention and treatment. Oxid Med Cell Longev, 2014, 860479. https://doi.org/10.1155/2014/860479
[13] Huck, L. A., & Leigh, W. J. (2010). A bettersunscreen: structural effects on spectralproperties. Journal of Chemical Education, 87(12), 1384–1387.
[14] Shang, Y. J., Jin, X. L., Shang, X. L., Tang, J. J., Liu, G. Y., Dai, F., … Zhou, B. (2010). Antioxidant capacity of curcumin-directed analogues: Structure-activity relationship and influence of microenvironment. Food Chemistry, 119(4), 1435–1442. https://doi.org/10.1016/j.foodchem.2009.09.024
[15] Handayani, S. (2009). Synthesis and activity test of two asymmetric dibenzalacetones as potential sunscreen material. In L. Kai (Ed.), Chemical, Biological, and Environmental Engineering: Proceedings of the International Conference on CBEE 2009 (pp. 119–122). Singapore: World Scientific. https://doi.org/https://doi.org/10.1142/9789814295048_0024
[16] Handayani, S., & Arty, I. S. (2009). Synthesis and activity test of some compounds 1,5-diphenyl-1,4-pentadiene-3-one as potensial sunsreen material. In International Seminar on Science and Tecnology (pp. 24–26). Yogyakarta.
[17] Handayani, S., & Indyah Sulistyo, A. (2008). Synthesis of hydroxyl radical scavengers from benzalacetone and its derivatives. Journal of Physical Science, 19(2), 61–68. Retrieved from http://web.usm.my/jps/19-2-08/article 19-2-7.pdf
[18] Handayani, S., Matsjeh, S., Anwar, C. and Atun, S. (2010). Synthesis and activity test as antioxidant of two hydroxydibenzalacetones. In Pure and Applied Chemistry international Conference 2010 Proceedings (pp. 686–688). Ubon Ratchathani.
[19] Du, Z. Y., Bao, Y. D., Liu, Z., Qiao, W., Ma, L., Huang, Z. S., … Chan, A. S. C. (2006). Curcumin analogs as potent aldose reductase inhibitors. Archiv Der Pharmazie, 339(3), 123–128. https://doi.org/10.1002/ardp.200500205
[20] Du, Z. Y., Liu, R. R., Shao, W. Y., Mao, X. P., Ma, L., Gu, L. Q., … Chan, A. S. C. (2006). α-Glucosidase inhibition of natural curcuminoids and curcumin analogs. European Journal of Medicinal Chemistry, 41(2), 213–218. https://doi.org/10.1016/j.ejmech.2005.10.012
[21] 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. https://doi.org/10.1016/j.jphotobiol.2011.06.007
[22] Dutra, E. A., Oliveira, D. A. G. da C. e, Kedor-, E. R. M., Hackmann, & Santoro, M. I. R. M. (2004). Determination of sun protection factor (SPF) of sunscreens by ultraviolet spectrophotometry. Revista Brasileira de Ciências Farmacêuticas, 40(3), 381–385. https://doi.org/10.1590/S1516-93322004000300014
[23] Sayre, R. M., Agin, P. P., Le Vee, G. J., & Marlowe, E. (1979). A Comparison of in vivo and in vitro testing of sunscreening formulas. Photochemistry and Photobiology, 29, 559–566. https://doi.org/10.1111/j.1751-1097.1979.tb07090.x
[24] Diffey, B. L. (1994). A method for broad spectrum classification of sunscreens. International Journal of Cosmetic Science, 16, 47–52.
[25] Molyneux, P. (2004). The use of the stable free radical diphenylpicryl- hydrazyl (DPPH) for estimating antioxidant activity. Songklanakarin Journal of Science and Technology, 26(June 2003), 211–219. https://doi.org/10.1287/isre.6.2.144
[26] Nielsen, A. T., & Houlihan, W. J. (2011). The Aldol Condensation. Organic Reactions, 16, 1–438. https://doi.org/10.1002/0471264180.or016.01
[27] Shin, D., Song, D., Jung, K., & Moon, J. (2001). Photochemical transformation of chalcone derivatives. Journal of Photoscience, 8, 9–12.
[28] Song, D. M., Jung, K. H., Moon, J. H., & Shin, D. M. (2003). Photochemistry of chalcone and the application of chalcone-derivatives in photo-alignment layer of liquid crystal display. Optical Materials, 21(1–3), 667–671. https://doi.org/10.1016/S0925-3467(02)00220-3
[29] Shindo, Y., Horie, K., & Mita, I. (1984). Photoisomerization of ethyl cinnamate in dilute solutions. Journal of Photochemistry, 26(2–3), 185–192. https://doi.org/10.1016/0047-2670(84)80037-4
[30] Leopoldini, M., Marino, T., Russo, N., & Toscano, M. (2004). Antioxidant properties of phenolic compounds : H-atom versus electron transfer mechanism. Journal of Physical Chemistry A, 108(22), 4916–4922. https://doi.org/10.1021/jp037247d
[31] Ohkatsu, Y., & Nishiyama, T. (1998). Phenolic Antioxidants-Effect of o-Alkyl Substituents. Sekiyu Gakkaishi, 41(4), 251–257.
[32] Ohkatsu, Y., & Nishiyama, T. (2000). Phenolic antioxidants-effect of ortho-substituents. Polymer Degradation and Stability, 67(June 1999), 313–318.
[33] Najafi, M. (2014). On the antioxidant activity of the Ortho and Meta substituted Daidzein derivatives in the gas phase and solvent environment. Journal of the Mexican Chemical Society, 58(1), 36–45.
[2] Dahle, J., & Kvam, E. (2003). Induction of delayed mutations and chromosomal instability in fibroblasts after UVA-, UVB-, and X-radiation. Cancer Research, 63(7), 1464–1469.
[3] Jiang, Y., Rabbi, M., Kim, M., Ke, C., Lee, W., Clark, R. L., … Marszalek, P. E. (2009). UVA generates pyrimidine dimers in DNA directly. Biophysical Journal, 96(3), 1151–1158. https://doi.org/10.1016/j.bpj.2008.10.030
[4] Fisher, G. J., Kang, S., Varani, J., Bata-Csorgo, Z., Wan, Y., Datta, S., & Voorhees, J. J. (2002). Mechanisms of photoaging and chronological skin aging. Archives of Dermatology, 138(11), 1462–1470. https://doi.org/10.1001/archderm.138.11.1462
[5] Boyd, A. S., Naylor, M., Cameron, G. S., Pearse, A. D., Gaskell, S. A., & Neldner, K. H. (1995). The effects of chronic sunscreen use on the histologic changes of dermatoheliosis. Journal of the American Academy of Dermatology, 33(6), 941–946. https://doi.org/10.1016/0190-9622(95)90284-8
[6] van Praag, M. C. G., Roza, L., Boom, B. W., Out-Luijting, C., Henegouwen, J. B. A. B., Vermeer, B. J., & Mommaas, A. M. (1993). Determination of the photoprotective efficacy of a topical sunscreen against UVB-induced DNA damage in human epidermis. Journal of Photochemistry and Photobiology, B: Biology, 19(2), 129–134. https://doi.org/10.1016/1011-1344(93)87107-X
[7] Liardet, S., Scaletta, C., Panizzon, R., Hohlfeld, P., & Laurent-Applegate, L. (2001). Protection against pyrimidine dimers, p53, and 8-hydroxy-2′-deoxyguanosine expression in ultraviolet-irradiated human skin by sunscreens: Difference between UVB + UVA and UVB alone sunscreens. Journal of Investigative Dermatology, 117(6), 1437–1441. https://doi.org/10.1046/j.0022-202x.2001.01580.x
[8] Nohynek, G. J., & Schaefer, H. (2001). Benefit and risk of organic ultraviolet filters. Regulatory Toxicology and Pharmacology, 33(3), 285–299. https://doi.org/10.1006/rtph.2001.1476
[9] Shaath, N. A. (2005). The chemistry of ultraviolet filters. In N. A. Shaath (Ed.), Sunscreens: Regulations and commercial development (third, pp. 217–238). Boca raton: Tailor & Francis Group.
[10] Kammeyer, A., & Luiten, R. M. (2015). Oxidation events and skin aging. Ageing Research Reviews, 21, 16–29. https://doi.org/10.1016/j.arr.2015.01.001
[11] Birch-Machin, M. A., & Bowman, A. (2016). Oxidative stress and ageing. British Journal of Dermatology, 175, 26–29. https://doi.org/10.1111/bjd.14906
[12] Godic, A., Poljšak, B., Adamic, M., & Dahmane, R. (2014). The role of antioxidants in skin cancer prevention and treatment. Oxid Med Cell Longev, 2014, 860479. https://doi.org/10.1155/2014/860479
[13] Huck, L. A., & Leigh, W. J. (2010). A bettersunscreen: structural effects on spectralproperties. Journal of Chemical Education, 87(12), 1384–1387.
[14] Shang, Y. J., Jin, X. L., Shang, X. L., Tang, J. J., Liu, G. Y., Dai, F., … Zhou, B. (2010). Antioxidant capacity of curcumin-directed analogues: Structure-activity relationship and influence of microenvironment. Food Chemistry, 119(4), 1435–1442. https://doi.org/10.1016/j.foodchem.2009.09.024
[15] Handayani, S. (2009). Synthesis and activity test of two asymmetric dibenzalacetones as potential sunscreen material. In L. Kai (Ed.), Chemical, Biological, and Environmental Engineering: Proceedings of the International Conference on CBEE 2009 (pp. 119–122). Singapore: World Scientific. https://doi.org/https://doi.org/10.1142/9789814295048_0024
[16] Handayani, S., & Arty, I. S. (2009). Synthesis and activity test of some compounds 1,5-diphenyl-1,4-pentadiene-3-one as potensial sunsreen material. In International Seminar on Science and Tecnology (pp. 24–26). Yogyakarta.
[17] Handayani, S., & Indyah Sulistyo, A. (2008). Synthesis of hydroxyl radical scavengers from benzalacetone and its derivatives. Journal of Physical Science, 19(2), 61–68. Retrieved from http://web.usm.my/jps/19-2-08/article 19-2-7.pdf
[18] Handayani, S., Matsjeh, S., Anwar, C. and Atun, S. (2010). Synthesis and activity test as antioxidant of two hydroxydibenzalacetones. In Pure and Applied Chemistry international Conference 2010 Proceedings (pp. 686–688). Ubon Ratchathani.
[19] Du, Z. Y., Bao, Y. D., Liu, Z., Qiao, W., Ma, L., Huang, Z. S., … Chan, A. S. C. (2006). Curcumin analogs as potent aldose reductase inhibitors. Archiv Der Pharmazie, 339(3), 123–128. https://doi.org/10.1002/ardp.200500205
[20] Du, Z. Y., Liu, R. R., Shao, W. Y., Mao, X. P., Ma, L., Gu, L. Q., … Chan, A. S. C. (2006). α-Glucosidase inhibition of natural curcuminoids and curcumin analogs. European Journal of Medicinal Chemistry, 41(2), 213–218. https://doi.org/10.1016/j.ejmech.2005.10.012
[21] 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. https://doi.org/10.1016/j.jphotobiol.2011.06.007
[22] Dutra, E. A., Oliveira, D. A. G. da C. e, Kedor-, E. R. M., Hackmann, & Santoro, M. I. R. M. (2004). Determination of sun protection factor (SPF) of sunscreens by ultraviolet spectrophotometry. Revista Brasileira de Ciências Farmacêuticas, 40(3), 381–385. https://doi.org/10.1590/S1516-93322004000300014
[23] Sayre, R. M., Agin, P. P., Le Vee, G. J., & Marlowe, E. (1979). A Comparison of in vivo and in vitro testing of sunscreening formulas. Photochemistry and Photobiology, 29, 559–566. https://doi.org/10.1111/j.1751-1097.1979.tb07090.x
[24] Diffey, B. L. (1994). A method for broad spectrum classification of sunscreens. International Journal of Cosmetic Science, 16, 47–52.
[25] Molyneux, P. (2004). The use of the stable free radical diphenylpicryl- hydrazyl (DPPH) for estimating antioxidant activity. Songklanakarin Journal of Science and Technology, 26(June 2003), 211–219. https://doi.org/10.1287/isre.6.2.144
[26] Nielsen, A. T., & Houlihan, W. J. (2011). The Aldol Condensation. Organic Reactions, 16, 1–438. https://doi.org/10.1002/0471264180.or016.01
[27] Shin, D., Song, D., Jung, K., & Moon, J. (2001). Photochemical transformation of chalcone derivatives. Journal of Photoscience, 8, 9–12.
[28] Song, D. M., Jung, K. H., Moon, J. H., & Shin, D. M. (2003). Photochemistry of chalcone and the application of chalcone-derivatives in photo-alignment layer of liquid crystal display. Optical Materials, 21(1–3), 667–671. https://doi.org/10.1016/S0925-3467(02)00220-3
[29] Shindo, Y., Horie, K., & Mita, I. (1984). Photoisomerization of ethyl cinnamate in dilute solutions. Journal of Photochemistry, 26(2–3), 185–192. https://doi.org/10.1016/0047-2670(84)80037-4
[30] Leopoldini, M., Marino, T., Russo, N., & Toscano, M. (2004). Antioxidant properties of phenolic compounds : H-atom versus electron transfer mechanism. Journal of Physical Chemistry A, 108(22), 4916–4922. https://doi.org/10.1021/jp037247d
[31] Ohkatsu, Y., & Nishiyama, T. (1998). Phenolic Antioxidants-Effect of o-Alkyl Substituents. Sekiyu Gakkaishi, 41(4), 251–257.
[32] Ohkatsu, Y., & Nishiyama, T. (2000). Phenolic antioxidants-effect of ortho-substituents. Polymer Degradation and Stability, 67(June 1999), 313–318.
[33] Najafi, M. (2014). On the antioxidant activity of the Ortho and Meta substituted Daidzein derivatives in the gas phase and solvent environment. Journal of the Mexican Chemical Society, 58(1), 36–45.
Published
2018-11-29
How to Cite
HARIZAL, Harizal; HIDAYANTO, Ariyo Prabowo; SARI, Nindya Wulan.
SYNTHESIS AND PRELIMINARY EVALUATION OF 3,3’-DIHYDROXY-4,4’-DIMETHOXYDIBENZYLIDENEACETONE AS SUNSCREEN AND ANTIOXIDANT ACTIVE COMPOUND.
JURNAL KIMIA MULAWARMAN, [S.l.], v. 16, n. 1, p. 49-59, nov. 2018.
ISSN 2476-9258.
Available at: <http://jurnal.kimia.fmipa.unmul.ac.id/index.php/JKM/article/view/665>. Date accessed: 20 apr. 2024.
doi: https://doi.org/10.30872/jkm.v16i1.665.
Issue
Section
Artikel
Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
This license requires that reusers give credit to the creator. It allows reusers to distribute, remix, adapt, and build upon the material in any medium or format, even for commercial purposes. If others remix, adapt, or build upon the material, they must license the modified material under identical terms.
BY: Credit must be given to you, the creator.
SA: Adaptations must be shared under the same terms.
