SINTESIS SENYAWA TABIR SURYA TURUNAN KALIKS[4]RESORSINARENA SERI BENZOFENON DAN SINAMAT DARI p-ANISALDEHIDA; SYNTHESIS OF SUNSCREEN COMPOUNDS OF CALIX[4]RESORCINARENE DERIVATIVES OF BENZOPHENONE AND CINNAMATE SERIES FROM p-ANISALDEHYDE

Indarto, Jumina

2013 | Disertasi | PROGRAM STUDI PASCASARJANA ILMU KIMIA

Synthesis of C-4-methoxyphenylcalix[4]resorcinaryl octacinnamate (CMPCRCI) and benzoyl C-4-methoxyphenylcalix[4]resorcinaryl octaacetate (BCMPCRAC) have been carried out from p-anisaldehyde. The structure elucidation of the products were performed by FTIR, and 1H-NMR spectrometers. The sun protection factor (SPF) of the final products was determined using UVVis spectrophotometer. The first step was reaction between p-anisaldehyde and resorcinol in the presence of HCl catalyst in ethanol solvent at 78 oC for 24h to give C-4- methoxyphenylcalix[4]resorcinarene (CMPCR) in 98% yield. The second step was base-catalyzed-esterification of CMPCR with cinamoyl chloride to produce CMPCRCI in 98% yield and was acid-catalyzed-esterification with acetic anhidride to produce C-4-methoxyphenylcalix[4]resorcinaryl octaacetate (CMPCRAC) in 88% yield. The third step was Friedel-Crafts acylation of CMPCRAC product with benzoyl chloride to afford BCMPCRAC in 74% yield. Characterization of synthesized products using UV-Vis spectrophotometer showed that CMPCRCI has a maximum wavelength at 284 nm, indicating that it can be used as UV-B sunscreen compound and BCMPCRAC at 280 nm indicating that it can be used as UV-C sunscreen compound. The SPF values at the concentration of 10 ppm were 23.82 for CMPCRCI and 1.35 for BCMPC

Kata Kunci : p-anisaldehida; tabir surya; benzofenon; sinamat; kaliks[4]resorsinarena