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Synthesis of Novel Kojic Acid Derivative and Its Anti-pigmentation Effect  

Kim Ki Ho (R&D Center, Bioland Ltd.)
Kim Ki Soo (R&D Center, Bioland Ltd.)
Kim Jin Guk (R&D Center, Bioland Ltd.)
Han Chang Sung (R&D Center, Bioland Ltd.)
Kim Young Heui (R&D Center, Bioland Ltd.)
Park Soo Nam (Department of Fine Chemistry, Seoul National University of Technology)
Publication Information
Journal of the Society of Cosmetic Scientists of Korea / v.30, no.3, 2004 , pp. 409-414 More about this Journal
Abstract
Kojic acid is well known for its anti-pigmentation effect with tyrosinase inhibition activity. However, kojic acid is a unstable compound. In order to improve stability, kojic acid derivative, kojic acid $6-O-2, was synthesized with $O-pentaacetyl-{\beta}-D-glucose$ through the regio- and stereo-selective glycosylation of 6-OH group of kojic acid. High yield $(80\%)$ was obtained by the use of Lewis acid and organic base in nonpolar solvent. Hydrolysis of KTGP with the aid of sodium methoxide in methanol afforded kojic acid $6-O-{\beta}-D-glucopyranoside$ (KGP), which was confirmed by $^1H-NMR\;and\;^{13}C-NMR$ KGP is freely soluble in water and soluble in methanol and ethanol. Inhibition activity of KGP for tyrosinase was investigated by measuring the activity of mushroom tyrosinase compared with those of ascorbic acid, kojic acid, and arbutin. The free radical-scavenger activity was determined by the 1,1-diphenyl- 2-picrylhydrazyl (DPPH) assay. In toxicity assay, KGP was much less toxic than kojic acid and arbutin, Therefore, glycosylation of kojic acid may be useful for the development of stable kojic acid derivatives.
Keywords
kojic aid; anti-pigmentation; glycosylation; tyrosinase;
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