Enzymatic Synthesis of Piceid Octanoate

Synthesis of piceid octanoate was previously reported by Larrosa et al. [46 (link)]. Briefly, PIC-OCT was prepared via enzymatic acylation of piceid using Novozym 435, lipase immobilized on macroporous acrylic resin. The reaction was carried out in tert-butyl alcohol (10 mL for 1 g of piceid) by adding vinyl octanoate (15 mL, 3 eq). The mixture was stirred in an orbital shaker at 60 °C for 16 h. The enzyme was decanted and separated. The solvent was evaporated and the product was purified via flash column chromatography (CH2Cl2/MeOH from 95:5 to 85:15) to obtain the corresponding PIC-OCT as a white solid (yield 83%, purity 98.5%).