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[Kurkumin merupakan senyawa multipoten yang terdapat dalam tanaman kunyit.Tanaman kunyit banyak terdapat di Indonesia dan negara Asia lainnya. Kunyitsering digunakan sebagai bahan jamu, bumbu masakan, dan perwarna makanan.Meskipun kurkumin telah menunjukkan banyak manfaat, kurkumin masih belumdiakui sebagai senyawa obat. Hal ini disebabkan bioavailabilitas kurkumin buruk.Salah satu alasan buruknya bioavailabilitas kurkumin adalah kelarutan kurkuminpada cairan biologis rendah dan stabilitasnya kurang baik. Usaha untukmeningkatkan bioavailabilitas kurkumin telah dilakukan, salah satunya adalahdengan melakukan sintesis analog kurkumin. Substitusi basa Mannich padasenyawa organik dapat meningkatkan kelarutan senyawa tersebut. Berdasarkanpemikiran tersebut, senyawa derivat Mannich dihidropirimidin-2-on kurkumindicoba untuk disintesis. Percobaan sintesis ini dilakukan melalui tiga tahap reaksi,yaitu (1) sintesis 4,6-dimetil-2-hidroksipirimidin HCl, (2) sintesisdihidropirimidin-2-on kurkumin, dan (3) Substitusi basa Mannich padadihidropirimidin-2-on kurkumin. Sintesis tahap (1) dilakukan dengan merefluksurea dan asetil aseton dalam pelarut etanol pada suhu 70oC memperoleh rendemen77,59%; tahap (2) dilakukan dengan merefluks senyawa 4,6-dimetil-2-hidroksipirimidin HCl dengan vanilin dalam campuran pelarut etanol dan toluenapada suhu 100oC memperoleh rendemen 94,81%; tahap (3) dilakukan denganmengaduk senyawa dihidropirimidin-2-on kurkumin dalam pelarut asam asetatglasial pada suhu 70oC. Dari hasil elusidasi struktur diketahui bahwa produksenyawa sintesis tahap (3) belum diperoleh., Curcumin is a multipotent compound contained in turmeric. Turmeric is widelyavailable in Indonesia and other Asian countries. Turmeric is often used as amedicinal, seasoning, and food coloring. Although curcumin has shown manybenefits, curcumin is still not recognized as medicinal compounds. This is due topoor bioavailability of curcumin. The reasons for poor bioavailability of curcuminare the low solubility of curcumin in biological fluids and poor stability. Attemptshave been done to improve the bioavailability of curcumin, one of which is toperform synthesis of curcumin analogues. Mannich base substitution in organiccompounds can increase the solubility. Based on that idea, Mannich derivatives ofcompounds dihydropyrimidine-2-one tried to be synthesized. This synthesisexperiments conducted through three reaction steps, namely (1) the synthesis of4,6-dimethyl-2-hydroxypyrimidine HCl, (2) synthesis of dihydropyrimidine-2-onecurcumin, and (3) substitution Mannich bases on dihydropyrimidine-2-onecurcumin , Synthesis stage (1) conducted by refluxing urea and acetyl acetone inethanol at 70°C obtained 77.59% yield; Step (2) is carried out by refluxing thecompound 4,6-dimethyl-2-hydroxypyrimidine HCl with vanilin in a solventmixture of ethanol and toluene at 100oC obtained 94.81% yield; Step (3) carriedout by stirring dihydropyrimidine-2-one curcumin compound in glacial acetic acidsolvent at 70°C. From the elucidation results, it is known that the product ofsynthesis stage (3) has not been obtained.] |
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