Sintesis Senyawa Vanilil Metil Keton dan Uji Aktivitas Antiinflamasi terhadap Enzim COX-1 dan COX-2 melalui Analisis In Silico

Khoirotul Ummah, Robby Gus Mahardika, Ana Mardliyah


This study reports the synthesis of vanillyl methyl ketone from eugenol through Wacker oxidation and anti-inflammatory activity test toward COX-1 and COX-2 through in silico analysis. Wacker oxidation process was catalyzed by PdCl2 and CuCl2 using DMF solvent under the aerobic condition at room temperature for 48 hours. The product of the synthesis was purified by column chromatography and was characterized by NMR, IR, and MS spectroscopy. Characterization by spectroscopic methods showed that vanillyl methyl ketone was formed with a yield of 45% and vanillin (3%) was produced as a by-product. The anti-inflammatory activity of vanillyl methyl ketone was carried out by molecular docking toward   COX-1 and COX-2 obtained from PDB. The analysis showed that the anti-inflammatory activity and selectivity toward COX-2 of vanillyl methyl ketone was higher than eugenol. This was shown by the low binding energy affinity and the number of hydrogen bonds formed between the vanillyl methyl ketone and the active site of the enzyme.


Keywords: eugenol, Wacker, vanillyl methyl ketone, antiinflammatory, in silico


Pada penelitian ini dilakukan sintesis senyawa vanilil metil keton dari eugenol melalui oksidasi Wacker serta dilakukan uji aktivitas antiinflamasi terhadap enzim COX-1 dan COX-2 melalui analisis in silico. Proses oksidasi Wacker dikatalisis oleh PdCl2 dan CuCl2 menggunakan pelarut DMF dalam kondisi aerob pada suhu ruang selama 48 jam. Senyawa hasil sintesis dipisahkan menggunakan kolom kromatografi dan dikarakterisasi menggunakan spektroskopi NMR, IR dan MS. Hasil karakterisasi menunjukkan bahwa senyawa vanilil metil keton telah terbentuk dengan randemen sebanyak 45% dan juga dihasilkan senyawa vanillin (3%) sebagai produk samping. Aktivitas antiinflamasi senyawa vanilil metil keton dilakukan dengan docking molekuler terhadap enzim COX-1 dan COX-2 yang diperoleh dari PDB. Hasil analisis menunjukkan bahwa aktivitas antiinflamasi dan selektivitas terhadap COX-2 pada senyawa vanilil metil keton lebih tinggi dibandingkan eugenol. Hal ini ditunjukkan melalui rendahnya afinitas energi pengikatan dan banyaknya ikatan hidrogen yang terbentuk antara vanilil metil keton dengan sisi aktif enzim.


Kata kunci : eugenol, Wacker, vanilil metil keton, antiinflamasi, in silico

Full Text:




  • There are currently no refbacks.

Kirim NME Creative Commons

This work is licensed under NME Creative Commons Atribusi-NonKomersial-BerbagiSerupa 4.0 Internasional.
ALCHEMY is managed by
© All rights reserved 2016. Alchemy, Journal of Chemistry, eISSN 2460-6871


View My Stats