Sintesis senyawa Analog Kurkumin 2,6-bis-(4-hidroksi-3-metoksibenzilidin) Sikloheksanon dengan katalis HCl dan NaOH

Riyadi, Slamet (2020) Sintesis senyawa Analog Kurkumin 2,6-bis-(4-hidroksi-3-metoksibenzilidin) Sikloheksanon dengan katalis HCl dan NaOH. Sarjana thesis, UIN Sunan Gunung Djati Bandung.

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Abstract

Sintesis senyawa analog kurkumin telah banyak dilakukan, salah satu senyawa yang telah berhasil disintesis yaitu 2,6-bis-(4-hidroksi-3-metoksibenzilidin)-piperidin 4-on (monohidrat hidroklorida). Modifikasi senyawa tersebut dilakukan dengan mengganti gugus β-diketon menjadi monoketon. Berdasarkan analisis tersebut dapat dikembangkan sintesis senyawa analog kurkumin 2,6-bis-(4’-hidroksi-3’-metoksibenzilidin)-sikoheksanon dengan material awal vanillin dan sikloheksanon. Sintesis dilakukan berdasarkan reaksi kondensasi Claisen – Schmidt dalam suasana asam dan basa dilakukan dalam suhu ruang. Kemurnian hasil sintesis ditetapkan berdasarkan uji kromatografi lapis tipis, KLT-2D, dan uji titik leleh. Sedangkan struktur senyawa ditetapkan berdasarkan spektroskopi 1H-NMR dan 13C-NMR. Hasil penelitian ini menunjukkan bahwa pada sintesis dalam suasana asam menghasilkan rendemen yang lebih baik dibandingkan dalam suasana basa. Titik lebur senyawa hasil sintesis pada suasana asam diperoleh 166,9 – 179,9 °C dan dalam suasana basa 164,7 – 177,8 °C. Sedangkan analisis struktur senyawa hasil sintesis menggunakan spektra NMR diidentifikasi sebagai senyawa analog kurkumin dengan rumus molekul C22H22O5. Synthesis curcumin analogue compound has been widely carried out, one compound that has been successfully synthesized is 3,5-bis-(4-hisroxy-3-methoxybenzilidine)-pipiridion-monohydrate (monohydrate hydrochloride). The modification is success by replacing the β-diketone group into monoketone. Based on analysis the synthesis of curcumin analog compounds 3,5-bis- (4-hidroksi-3-methoxybenzylidine) can be developed by cyclohexanone with material of vanillin and cyclohexanone. Synthesis is carried out based on the Claisen-Schmidt condensation reaction in acidic and basic conditions carried out at room temperature. The purity of the synthesis results was determined based on thin layer chromatography test, KLT-2D, and melting point test. While the structure of the compound was determined based on 1H-NMR and 13C-NMR. The results of this study indicate that the synthesis in an acidic atmosphere produces a better yield than in an base atmosphere. The melting point of the synthesized compound under acidic conditions is obtained 166.9 - 179.9 °C and under alkaline 164.7 - 177.8 °C. While the structural analysis of the synthesized compound using NMR was identified as an analog compound of curcumin with an molecular formula C22H22O5.

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