SINTESIS LAKTOGENIN DARI TETRAHIDROFURAN-3-KARBOKSALDEHIDA DAN 2-ASETIL-γ-BUTIROLAKTON DENGAN KATALIS NATRIUM METOKSIDA
Abstract: Acetogenin compound
known for its activity as anticancer by inhibited the NADHubiquinone reductase
contained in the mitochondria. These compounds with high liphophilicity
properties have a weakness in solubility with log P 8.44, so modifications to
improve the solubility by maintaining a core group of tetrahydrofuran and
γ-lactone as well as shortening the alkyl chain is needed. The modified
compounds was lactogenin or 3-(3- (tetrahydrofuran-3-yl) acryloyl)
dihydrofuran-2(3H)-one) that have a log P 0.90 and is expected to have a better
solubility properties than acetogenin. Lactogenin synthesis was based on
cross-aldol condensation reaction by reacting tetrahyrdofuran-3-carbaldehyde
and 2-acetyl-γ-butyrolactone using sodium methoxide as catalyst. The
synthesized compounds were red solution with specific smell. The TLC result
showed the new products at Rf 0.314. The purity test by gas chromatography
showed 74.07% purity. The structure elucidation by infrared and mass
spectroscopy showed that the synthesized compound was β-hydroxy lactogenin or
3-(3-hydroxy-3-(tetrahydrofuran-3-yl) propanoyl) dihydrofuran-2(3H)-one.
Keywords: NADH-ubiquinone
oksidoreduktase, lactogenin, cross-aldol condensation reaction, β-hydroxy
lactogenin
Penulis: Jeffy Julianus,
Laurensius Widi Andhika Putra
Kode Jurnal: jpfarmasidd130306
