Transformation of Eugenol and Safrole into Hydroxychavicol

Budi Arifin (Department of Chemistry, Bogor Agricultural University, Kampus IPB Dramaga, Bogor 16680)
Dumas Flis Tang (Department of Chemistry, Bogor Agricultural University, Kampus IPB Dramaga, Bogor 16680)
Suminar Setiati Achmadi (Department of Chemistry, Bogor Agricultural University, Kampus IPB Dramaga, Bogor 16680)

Indonesian Journal of Chemistry
Vol 15, No 1 (2015)

Hydroxychavicol is found in betel leaf at low concentration and is reported to have antibacterial, anti-inflammatory, antioxidant, anticancer, and antimutagenic activities. This study aimed to synthesize hydroxychavicol from eugenol and safrole. Isolation of eugenol from clove oil by alkaline extraction method gave 71% yield, while the isolation of safrole from lawang oil by alkaline extraction method, followed by purification using preparative thin layer chromatography, gave 7% yield. Eugenol demethylation and safrole demethylenation with AlCl3 reagent were successfully produced hydroxychavicol. The yields were 28% and 24%, respectively. Mechanisms of the synthesis are proposed in this article.