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Citation: LI Chang, SUN Jingyang, ZHI Defu, TIAN Tian, CHEN Yanhua, ZHAO Longxuan, ZHAO Chunhui. Synthesis, Characterization and Whitening Activity of Glucoside-phenols Conjugates[J]. Chinese Journal of Applied Chemistry, ;2016, 33(7): 780-791. doi: 10.11944/j.issn.1000-0518.2016.07.160031 shu

Synthesis, Characterization and Whitening Activity of Glucoside-phenols Conjugates

LI Chang ^a ,
SUN Jingyang ^a ,
ZHI Defu ^c ,
TIAN Tian ^a ,
CHEN Yanhua ^a ,
ZHAO Longxuan ^a,b,, ,
ZHAO Chunhui ^b,,

a.
a. School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian, Liaoning 116029, China;
b.
b. Liaoning Provincial Key Laboratory of Biotechnology and Drug Discovery, Liaoning Normal University, Dalian, Liaoning 116029, China;
c.
c. Dalian Nationalities University College of Life Science, Dalian, Liaoning 116600, China

Corresponding author: ZHAO Longxuan, ZHAO Chunhui,
Received Date: 19 January 2016
Available Online: 11 May 2016
Fund Project:

Three alcohol intermediates were synthesized through protection of one side phenolic hydroxyl group, coupling with methyl bromoacetate, and reduction using p-dihydroxybenzene, m-dihydroxybenzene and o-dihydroxybenzene as lead compounds. These three intermediates coupled with three different glycogens to get nine targeting compounds. Similarly, we protected phenolic hydroxyl of 3-(4-hydroxyphenyl)-1-propanol, and then coupled it with three different glycogens to yield three target compounds. The twelve target compounds were characterized by IR, ¹H NMR, ¹³C NMR and HRMS. The study of whitening activity of these conjugates shows that compounds p-HQ-6a, m-HQ-7a, p-HQ-6b, m-HQ-6b, o-HQ-6b, p-HQ-6c, m-HQ-7c, L-3a and L-4b have significant inhibition to tyrosinase, among of them compounds o-HQ-6b and p-HQ-6c against tyrosinase are obviously better than the positive control of α-Abutin.
- arbutin,
- glycoside,
- whitening activity
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