SINTESIS ANALOG KURKUMIN DARI PIPERONAL, VERATRALDEHID DAN p-DIMETILAMINOBENZALDEHID SERTA PERBANDINGAN ELUSIDASI STRUKTUR ANTARA EKSPERIMEN DAN HASIL KAJIAN SPEKTROSKOPI DIDASARKAN METODE DFT-B3LYP/6-31G(d); SYNTHESIS OF CURCUMIN ANALOGUES FROM PIPERONAL, VERATRALDEHYDE AND p-DIMETHYLAMINOBENZALDEHYDE AND COMPARISON OF STRUCTURE ELUCIDATION BETWEEN THE EXPERIMENT AND THE RESULT OF SPECTROSCOPIC STUDIES USING DFT-B3LYP/6-31G(d) METHOD

MARIO ROWAN SOHILAIT, Harno Dwi Pranowo

2013 | Disertasi | PROGRAM STUDI S2 ILMU KIMIA

Several curcumin analogues have been synthesized via condensation reaction between acetone and several benzaldehyde derivatives. The products were analyzed using HPLC, MS, FT-IR, 1H and 13C-NMR. The condensation of acetone and benzaldehydes of piperonal, veratraldehyde and p-dimethylaminobenzaldehyde gave 1,5-bis(1,3-benzodioxol-5yl)penta-1,4-dien-3-one (pale yellow solid, 94.87% yield), 1,5-bis(3,4-dimethoxyphenyl)penta-1,4-dien-3-one (yellow solid, 83.38% yield) and 1,5-bis[4-(dimethylamino)phenyl]penta-1,4-dien-3-one (golden yellow, 92.05% yield), respectively. The spectroscopic prediction of the curcumin analogues were conducted using Gaussian’09 software with the method of DFT using B3LYP/6-31G(d) basis set. It was showed that these methods gave similar IR vibration, 1H and 13C-NMR spectra as those of experimental results.

Kata Kunci : Analog kurkumin; piperonal; veratraldehid; DFT-B3LYP; para-dimetilaminobenzaldehid