Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on melanin synthesis

Transesterification of arbutin and undecylenic acid vinyl ester was catalyzed by alkaline protease, Bioprase, in dimethylformamide to get arbutin derivative having undecylenic acid at 6-position of glucose moiety, 6-O-undecylenoyl p-hydroxyphenyl β-d-glucopyranoside. The reaction rate increased with increase of arbutin concentration, and when its concentration was 0.9 M, the conversion rate was more than 90% under addition of 2 M undecylenic acid vinyl ester. The obtained arbutin ester significantly suppressed melanin production in murine B16 melanoma cells.

Graphical abstractTransesterification of arbutin and undecylenic acid vinyl ester was catalyzed by protease to get arbutin derivative having undecylenic acid ester. The arbutin ester significantly suppressed melanin production in murine B16 melanoma cells.Figure optionsDownload full-size imageDownload as PowerPoint slide