SINTESIS C-4-ALKOKSIFENILKALIKS[4]PIROGALOLARIL BENZOAT-SINAMAT SEBAGAI SENYAWA TABIR SURYA; SYNTHESIS OF C-4-ALKOXYPHENYLCALIX[4]PYROGALLOLARYL BENZOATES-CINNAMATES AS SUNSCREEN COMPOUNDS

Harizal, N

2016 | Disertasi | FMIPA

Synthesis and preliminary evaluation of four derivatives of C-4- alkoxyphenylcalix[4]pyrogallolaryl benzoates-cinnamates as sunscreen compound have been successfully conducted. Two C-4-alkoxyphenylcalix[4]pyrogallolarene derivatives (Pg4OMe and Pg4OBn) were functionalized using two chromophore groups, benzoate and cinnamate groups, via esterification reaction in order to obtain sunscreen active compounds that have desired properties i.e. broad absorbance in the UV region, higher photostability, and lower cytotoxicity. Synthesis of target compounds was carried out through three consecutive steps comprising 1) benzylation of 4-hydroxybenzaldehyde, 2) preparation of C-4- alkoxyphenylcalix[4]pyrogallolarenes, and 3) O-benzoylation and Ocinnamoylation of C-4-alkoxyphenylcalix[4]pyrogallolarenes. Preliminay evaluation of four sunscreen active compound candidates were conducted to determine electronic absorbance profile, ?max, ?, photostability, and cytotoxicity to Vero cell. All four compounds prepared include Pg4OMe-DBz, Pg4OMe-DSn, Pg4OBn-DBz, and Pg4OBn-DSn in 37, 85, 30, and 46% yield, respectively. Absorbance profile of two C-4-alkoxyphenylcalix[4]pyrogallolaril benzoates (Pg4OMe-DBz and Pg4OBn-DBz) showed quite similar appearance at ?max 241 nm (UVC region), with log ? 5,23 and 5,28, respectively. Two compounds of C-4- alkoxyphenylcalix[4]pyrogallolaril cinnamates (Pg4OMe-DSn and Pg4OBn-DSn) also possessed quite similar absorbance curve at ?max 279 nm (UVC/UVB region), with log ? 5,41 and 5,44, respectively. Photostability test of four compounds indicated that both benzoate derivative compounds had better stability under UVB radiation compared to its cinnamate derivatives. Generally, all target compounds have low toxicity and tend to increase Vero cell growth even in higher concentration. Therefore, based on the result of sunscreen compound preliminary evaluation, it can be concluded that all target compounds, potentially, can be used as sunscreen compounds especially for UVC/UVB region.

Kata Kunci : calix[4]pyrogallolarene, sunscreen, benzoates, cinnamates