SINTESIS SERI BENZOAT-SINAMAT KALIKS[4]RESORSINARENA DAN BENZOIL-SINAMOIL KALIKS[4]RESORSINARENA SERTA UJI AKTIVITASNYA SEBAGAI TABIR SURYA DAN ADSORBEN Cr(III), Pb(II) DAN Cd(II)
I GUSTI MADE NGURAH BUDIANA, Prof. Drs. Jumina, Ph.D
2015 | Disertasi | S3 KimiaPada penelitian ini telah disintesis dan dikarakterisasi senyawa seri benzoat-sinamat dan benzoil-sinamoil kaliks[4]resorsinarena. Produk reaksi selanjutnya diuji aktivitasnya sebagai tabir surya dan adsorben Cr(III), Pb(II) dan Cd(II). Seri benzoat-sinamat kaliks[4]resorsinarena terdiri atas C-metilkaliks[4]resorsinaril oktabenzoat (CMKOB), C-metilkaliks[4]resorsinaril oktasinamat (CMKOS), C-fenilkaliks[4]-resorsinaril oktabenzoat (CFKOB) dan C-fenilkaliks[4]resorsinaril oktasinamat (CFKOS). Seri benzoil-sinamoil kaliks[4]-resorsinarena terdiri atas benzoil oktaetoksi kaliks[4]arena (BOEK), sinamoil oktaetoksi kaliks[4]arena (SOEK), benzoil C-fenilkaliks[4]-resorsinarena (BCFKR), sinamoil C-fenilkaliks[4]-resorsinarena (SCFKR), benzoil C-metilkaliks[4]resorsinarena (BCMKR) dan sinamoil C-metilkaliks[4]resorsinarena (SCMKR). Pengujian aktivitas tabir surya dilakukan dengan metode in vitro menggunakan spektrometer ultraviolet dan MTT assay. Pengujian aktivitas sebagai adsorben dilakukan dengan metode batch dalam variasi pH, waktu interaksi dan konsentrasi ion logam uji. Rendemen reaksi seri benzoat-sinamat kaliks[4]arena berturut-turut; 79,95% (CMKOB), 74,45% (CMKOS), 74,10% (CFKOB) dan 78,65% (CFKOS). Rendemen reaksi seri benzoil-sinamoil kaliks[4]-resorsinarena berturut-turut; 11,70% (BOEK), 25,81% (SOEK), 65,50% (BCFKR), 61,60% (SCFKR), 63,45% (BCMKR) dan 64,00% (SCMKR). Hasil uji aktivitas tabir surya menunjukkan bahwa nilai sun protection factor (SPF) spektronik senyawa CMKOB, CMKOS, CFKOB dan CFKOS cukup tinggi berturut-turut 36, 222, 10 dan 123 pada konsentrasi 0,05 mg/mL. Senyawa CMKOS dan CFKOS memiliki aktivitas tabir surya dengan nilai IC50 berturut-turut 12.006 ppm dan 17.800 ppm. Nilai IC50 pembanding merk Intersun sebesar 18.235 ppm. Adsorpsi seri benzoil-sinamoil kaliks[4]resorsinarena terhadap kation Cr(III), Pb(II) dan Cd(II) mencapai optimum pada pH 5-7 dan mengikuti kinetika pseudo orde kedua. Hasil kajian kesetimbangan adsorpsi menunjukkan bahwa model isoterm adsorpsi Langmuir lebih sesuai dibandingkan model Freundlich. Nilai kapasitas adsorpsi (μmol/g) dan energi adsorpsi (kJ/mol) oktaetoksi kaliks[4]arena dalam mengadsorpsi Cr(III), Pb(II) dan Cd(II) berturut-turut adalah (211,30; 26,46), (12,07; 26,64) dan (67,73; 26,46). Kapasitas adsorpsi (μmol/g) dan energi adsorpsi (kJ/mol) sinamoil C-fenilkaliks[4]resorsinarena berturut-turut adalah (277,91; 30,87), (59,88; 33,92) dan (17,04; 29,83). Kapasitas adsorpsi (μmol/g) dan energi adsorpsi (kJ/mol) benzoil C-fenilkaliks[4]resorsinarena berturut-turut adalah; (565,29; 24,58), (50,37; 30,57) dan (34,47; 31,51).
The synthesis and characterization of benzoate-cynnamate and benzoyl-cinnamoyl calix[4]resorcinarene series have been conducted. The products were examined for their activity as sunscreen and adsorbent of Cr(III), Pb(II) and Cd(II). The benzoate-cinnamate calix[4]resorcinarene series consist of C-methylcalix[4]-resorcinaryl octabenzoate (CMKOB), C-methylcalix[4]resorcinaryl octacinnamate (CMKOS), C-phenylcalix[4]resorcinaryl octabenzoate (CFKOB) dan C-phenylcalix-[4]resorcinaryl octacinnamate (CFKOS). The benzoyl-cinnamoyl calix[4]resorcinarene series consisted of benzoyl octaethoxy calix[4]resorcinarene (BOEK), cinnamoyl octaethoxy calix[4]resor-cinarene (SOEK), benzoyl C-phenylcalix[4]resorcinarene (BCFKR), cinnamoyl C-phenylcalix[4]-resorcinarene (SCFKR), benzoyl C-methylcalix-[4]resorcinarene (BCMKR) and cinnamoyl C-methylcalix[4]resorcinarene (SCMKR). Examination of sunscreen activity was done by in vitro method using ultraviolet spectrometer and MTT assay. Examination of activity as adsorbent was done by batch method under variation of acidity, interaction time and metal ion concentration. Percent yields of benzoate-cynnamate calix[4]arene series were; 79.95% (CMKOB), 74.45% (CFKOB), 74.10% (CFKOB) and 78.65% (CFKOS). Whereas percent yields of benzoyl-cinnamoyl calyx[4]resorcinarene series were 11.70% (BOEK), 25.807% (SOEK), 65.50% (BCFKR), 61.60% (SCFKR), 63.45% (BCMKR) and 64.00% (SCMKR). The result of activity test as sunscreen showed that sun protection factor (SPF) spectronic value of compound CMKOB, CMKOS, CFKOB and CFKOS are high enough i.e. 36, 222, 10 and 123 at 0.05 mg/mL. Both compound CMKOS and CFKOS have sunscreen activity, with the IC50 values 12.006 ppm and 17.800 ppm respectively. Whereas the IC50 value of Intersun was 18.235 ppm. The adsorption of benzoyl-cinnamoyl calix[4]resorcinarene series toward Cr(III), Pb(II) and Cd(II) are optimum at pH 5-7 and followed pseudo second order kinetic. The result of adsorption equilibirium study showed that Langmuir isotherm model was more applicable than Freundlich model. The adsorption capacity (μmol/g) and adsorption energy (kJ/mol) of octaethoxycalix[4]arene toward Cr(III), Pb(II) and Cd(II) were (211.30; 26.46), (12.07; 26.64) and (67.73; 26.46), whereas of cinnamoyl C-phenyl-calix[4]resorcinarene were (277.91; 30.87), (59.88; 33.92) and (17.04; 29.83). The adsorption capacity (μmol/g) and adsorption energy (kJ/mol) of benzoyl-C-phenylcalix[4]resorcinarene were (565.29; 24.58), (50.37; 30.57) and (34.47; 31.51).
Kata Kunci : benzoat, sinamat, benzoil, sinamoil, sintesis, tabir surya dan adsorben
