SINTESIS KALIKS[4]RESORSINARENA DARI TURUNAN VANILIN SEBAGAI SENYAWA AKTIF TABIR SURYA

HERRY SUSENO, Prof. Dr.Jumina; Prof. Dr. Harno Dwi Pranowo

2017 | Tesis | S2 Ilmu Kimia

Sintesis dan uji pendahuluan tiga senyawa C-4-aliloksi-3-metoksi-fenilkaliks[4] resorsinarena benzoat-sinamat sebagai senyawa tabir surya telah berhasil dilakukan. Dua turunan C-4-aliloksi-3-metoksifenilkaliks[4]resorsinarena difungsionalisasi dengan benzoat dan sinamat untuk memperoleh senyawa tabir surya. Sintesis dilakukan melalui tiga tahap reaksi yaitu sintesis 4-aliloksi-3-metoksibenzaldehida, C-4-aliloksi-3-metoksifenilkaliks[4]resorsinarena, dan C-4- aliloksi-3-metoksifenilkaliks[4]resorsinaril bensoat-sinamat. Elusidasi struktur senyawa yang dihasilkan dilakukan menggunakan spektrofotometer IR, spektrofotometer UV-Vis, 1H-NMR, 13C-NMR dan HR-MS. Pengujian produk yang dihasilkan meliputi penentuaan lamda maks dan koefisien ekstingsi molar, fotostabiltas, dan antioksidan. Senyawa hasil sintesis C-4-aliloksi-3-metoksifenilkaliks[4]resorsinarena, C-4-aliloksi-3-metoksifenilkaliks[4]resorsinaril oktabenzoat, C-4-aliloksi-3-metoksifenilkaliks[4]resorsinaril oktasinamat memiliki rendemen berturut-turut 86,6, 71,1, dan 65,5%; panjang gelombang maksimun 288, 293, dan 307 nm, koefisien ekstingsi molar 12,9, 39,1, dan 85,3 mol-1 L cm-1, SPF 5,97; 14,90, dan 26,99, IC50 0,54, 7,70; < 0,002 µg/mL. Ketiga senyawa hasil sintesis memiliki potensi sebagai senyawa tabir surya

Synthesis of three compounds of C-4-allyloxy-3-methoxyphenylcalix [4] resorcinarene benzoate-cinnamate as sunscreen have been conducted. Two of C-4-allyloxy-3-methoxyphenylcalix[4]resorcinarene were functionalized with benzoate and cinnamate to obtain the sunscreen compounds. The synthesis was carried out three stages of reaction. There were syntheses of 4-allyloxy-3-methoxyphenylchalix, C-4-allyloxy-3-methoxyphenyl chalix[4]resorcinarene, and C-4-allyloxy-3-methoxyphenyl chalix[4]resorcinaryl benzoate-cinnamate. Stuctural elucidation of products were performed using IR spectrometer, UV-Vis spectrometer, 1H-NMR, 13C-NMR and HR-MS. Tests of product were included the determination of lamda max and molar extinction coefficients, photostability, and antioxidants. The products of C-4-allyloxy-3-methoxyphenylcalix resorcinarene, C-4-allyloxy-3-methoxyphenylcalix[4]resorcinaryl octabenzoate, C-4-allyloxy-3-methoxyphenylcalix[4]resorcinaryl octacinamate were produced 86.6, 71.1 and 65.5% respectively, maximum wavelength 288, 293, and 307 nm; molar extinction coefficient 12.9, 39.1, and 85.3 mol-1 Lcm-1, SPF 5.97, 14.90, and 26.99, IC50 0.54, 7.70, < 0.002 µg/mL. The products have been potential as a sunscreen agents.

Kata Kunci : Calix[4]resorcinarene, sunscreen, cinnamate, benzoate