[Kurkumin merupakan senyawa multipoten yang terdapat dalam tanaman kunyit.
Tanaman kunyit banyak terdapat di Indonesia dan negara Asia lainnya. Kunyit
sering digunakan sebagai bahan jamu, bumbu masakan, dan perwarna makanan.
Meskipun kurkumin telah menunjukkan banyak manfaat, kurkumin masih belum
diakui sebagai senyawa obat. Hal ini disebabkan bioavailabilitas kurkumin buruk.
Salah satu alasan buruknya bioavailabilitas kurkumin adalah kelarutan kurkumin
pada cairan biologis rendah dan stabilitasnya kurang baik. Usaha untuk
meningkatkan bioavailabilitas kurkumin telah dilakukan, salah satunya adalah
dengan melakukan sintesis analog kurkumin. Substitusi basa Mannich pada
senyawa organik dapat meningkatkan kelarutan senyawa tersebut. Berdasarkan
pemikiran tersebut, senyawa derivat Mannich dihidropirimidin-2-on kurkumin
dicoba untuk disintesis. Percobaan sintesis ini dilakukan melalui tiga tahap reaksi,
yaitu (1) sintesis 4,6-dimetil-2-hidroksipirimidin HCl, (2) sintesis
dihidropirimidin-2-on kurkumin, dan (3) Substitusi basa Mannich pada
dihidropirimidin-2-on kurkumin. Sintesis tahap (1) dilakukan dengan merefluks
urea dan asetil aseton dalam pelarut etanol pada suhu 70oC memperoleh rendemen
77,59%; tahap (2) dilakukan dengan merefluks senyawa 4,6-dimetil-2-
hidroksipirimidin HCl dengan vanilin dalam campuran pelarut etanol dan toluena
pada suhu 100oC memperoleh rendemen 94,81%; tahap (3) dilakukan dengan
mengaduk senyawa dihidropirimidin-2-on kurkumin dalam pelarut asam asetat
glasial pada suhu 70oC. Dari hasil elusidasi struktur diketahui bahwa produk
senyawa sintesis tahap (3) belum diperoleh., Curcumin is a multipotent compound contained in turmeric. Turmeric is widely
available in Indonesia and other Asian countries. Turmeric is often used as a
medicinal, seasoning, and food coloring. Although curcumin has shown many
benefits, curcumin is still not recognized as medicinal compounds. This is due to
poor bioavailability of curcumin. The reasons for poor bioavailability of curcumin
are the low solubility of curcumin in biological fluids and poor stability. Attempts
have been done to improve the bioavailability of curcumin, one of which is to
perform synthesis of curcumin analogues. Mannich base substitution in organic
compounds can increase the solubility. Based on that idea, Mannich derivatives of
compounds dihydropyrimidine-2-one tried to be synthesized. This synthesis
experiments conducted through three reaction steps, namely (1) the synthesis of
4,6-dimethyl-2-hydroxypyrimidine HCl, (2) synthesis of dihydropyrimidine-2-one
curcumin, and (3) substitution Mannich bases on dihydropyrimidine-2-one
curcumin , Synthesis stage (1) conducted by refluxing urea and acetyl acetone in
ethanol at 70°C obtained 77.59% yield; Step (2) is carried out by refluxing the
compound 4,6-dimethyl-2-hydroxypyrimidine HCl with vanilin in a solvent
mixture of ethanol and toluene at 100oC obtained 94.81% yield; Step (3) carried
out by stirring dihydropyrimidine-2-one curcumin compound in glacial acetic acid
solvent at 70°C. From the elucidation results, it is known that the product of
synthesis stage (3) has not been obtained.]
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