Water → Dihydrocapsiate

Participants

Reaction Conditions

Reaction Steps

8-Methylnonanoic acid (1.54 g, 8.95 mmol) and vanillyl alcohol (1.34 g, 8.70 mmol) were measured and placed in a flask (25 ml) and dissolved in heptane (0.5 ml). Lipase PS-C “Amano” I (enzyme immobilized on ceramic: 335 mg) was added and the mixture was heated with stirring in an oil bath at 55° C. for 13.5 hours. After 2 to 3 hours of stirring with heating, attachment of water on the wall of the upper part of the flask was observed. The flask was returned to room temperature, heptane (5 ml) was added to the reaction mixture, and the mixture was stirred for 10 minutes. The immobilized enzyme and a small amount of precipitated vanillyl alcohol were removed by filtration. The filtrate was concentrated under reduced pressure, and the obtained oil (2.42 g) was analyzed by HPLC to find that dihydrocapsiate was contained in 97.2 area %. The mixture was partitioned with heptane (15 ml) and 10% aqueous citric acid solution (15 ml), and the aqueous layer was further extracted with heptane (15 ml). The combined heptane layer was washed with water (10 ml) and saturated brine (10 ml) and dried over anhydrous magnesium sulfate. Magnesium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure to give a mixture (2.42 g) of dihydrocapsiate and 8-methylnonanoic acid as a colorless oil. As a result of the analysis, the yield of dihydrocapsiate was 72.3%, and the purity was 99.6 area % by HPLC. The mixture contained 24.8 wt % of 8-methylnonanoic acid relative to dihydrocapsiate.

Provenance & Evidence