Esterification of Acetic Acid Anhydride with Eugenol and Its Activity as Antifungal

Abstract

The main contents of clove oil are phenolic compounds, namely eugenol, eugenol acetate and gallic acid, as well as flavonoids. One of the derivatives of the eugenol compound is acetyl eugenol which was developed by the esterification reaction between eugenol and acetic acid anhydride using the sonochemical method. The aim of this research is to synthesize the acetyl eugenol compound from the esterification reaction between eugenol and acetic acid anhydride  using sonochemical methods, to determine the sonication time that can produce the acetyl eugenol compound with the largest yield percentage, and to determine its antifungal activity against the Candida albicans fungus. Synthesis of acetyleugenol was sonicated for 90 minutes at a temperature of eighty degrees celsius. The % yield of the synthesized compound is calculated and continued with testing which includes solubility, melting point, FTIR, GC-MS. NMR tests, which are then tested for antifungal activity. The research results show that eugenol and acetic acid anhydride compounds with a NaOH catalyst can be synthesized using ultrasonic waves and produce a % yield of 3.49%. The resulting synthesis can melt starting at a temperature of thirty degrees celcius and can  dissolve in ethanol, methanol, chloroform and ether but does not dissolve in distilled water. H-NMR FTIR testing on the acetyl eugenol compound showed the presence of 0,866 (s,3H)- 6,62 (d,1H)- 6,47 (d, 1H)- 1,875 (t,2H)- 4,983 (s, 2H)- 1,255 (d, 2H)- 7,061 (d,1H)- 3,84 (s, 3H). Acetyleugenol with concentrations of 5% and  10% it shows the ability to act as an antifungal for Candida albicans.

Keywords: Acetyleugenol; Antifungal; Candida albicans; Esterification; Sonochemical