SINTESIS 3-METOKSI-2',4',4-TRIHIDROKSIKHALKON DARI VANILIN DAN RESORSINOL SERTA UJI AKTIVITASNYA SEBAGAI ANTIBAKTERI; SYNTHESIS AND ACTIVITY TEST OF 3-METHOXY-2',4',4-TRIHYDROXYCHALCONE FROM VANILLIN AND RESORCINOL AS ANTIBACTERIAL

Krisianto, Riko, Sabirin Matsjeh

2016 | Skripsi | Sekolah Vokasi

Chalcone is one of flavonoids that has antibacterial activity. However its existence in nature is very limited. That’s why it’s necessary to synthesis chalcone to get chalcone in large amount. The 3-methoxy-2',4',4-trihydroxychalcone is expected to be a good antibacterial because it has three alcohol groups. There are some steps to synthesis chalcone. The first steps is synthesis 2,4-dihydroxyacetophenone was synthesized via Friedel Craft acylation of resorcinol by glacial acetic acid and catalyzed by ZnCl2, which is refluxed for 20 minutes. The second is synthesis 3-methoxy-2',4',4-trihydroxychalcone. It was synthesized via Claisen Schmidt condensation from 2,4-dihydroxyacetophenone and vanillin catalyzed by montmorillonite KSF in absolute ethanol. This reaction was running in basic condition under stirring at room temperature for 48 hours, then refluxed the mixture for 24 hours. All the synthesized compounds were characterized and identified the structure using FTIR, GC-MS and 1H-NMR spectrometer. The chalcone was tested for its antibacterial activity using agar well diffusion tes against Gram Positive bacteria (Staphylococcus aureus, Bacillus cereus) and Gram Negative bacteria (Escherichia coli, Salmonella thiphymurium). The result showed 2,4-dihydroxyacetophenone yielded orange crystal solid in 62.50%, while 3-methoxy-2',4',4-trihydroxychalcone was yellow crystal solid has been synthesized in 27.75% yield. Antibacterial test showed that chalcone was active against both Gram Positive (Staphylococcus aureus, Bacillus cereus) and Gram Negative bacteria (Escherichia coli, Salmonella thiphymurium). The highest activity showed by its zone of inhibitions/concentration against Staphylococcus aureus for Gram Positive in 5.90/1000 mm/ppm and Escherichia coli for Gram Negative in 6.64/1000 mm/ppm.

Kata Kunci : acetophenon, chalcone, vanillin, antibacterial