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催化合成美白剂4-(1-苯乙基)-1,3-苯二酚及其性能研究
Synthesis and performance of a skin-whitening agent 4-(1-phenethyl)-1,3-benzenediol
徐源鸿, 许虎君
2017 (3):
153-158.
doi: 10.13218/j.cnki.csdc.2017.03.007
摘要
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采用浸渍法制备了二氧化硅负载磷钨酸催化剂,使用IR、XRD和SEM对其进行了表征,并用该催化剂催化间苯二酚与苯乙烯反应合成了美白剂4-(1-苯乙基)-1,3-苯二酚,经二甲苯重结晶后使用MS和1H NMR确定了产物的结构;应用酪氨酸酶活性抑制实验、Fe3+还原力和自由基抑制实验评价了4-(1-苯乙基)-1,3-苯二酚的美白和抗氧化活性,并与β-熊果苷进行了比较。结果表明,以L-酪氨酸为底物时,4-(1-苯乙基)-1,3-苯二酚对酪氨酸酶的半抑制浓度IC50＝0.010 5 g/L,明显低于β-熊果苷(IC50=0.64 g/L),4-(1-苯乙基)-1,3-苯二酚的美白效果远强于β-熊果苷;4-(1-苯乙基)-1,3-苯二酚对Fe3+还原力的半效应浓度EC50=0.033 g/L,去除羟基自由基的EC50=0.06 g/L,去除超氧自由基的EC50=0.32 g/L,与β-熊果苷的抗氧化能力相比,其对Fe3+还原力和去除超氧自由基的能力强于β-熊果苷。
A skin-whitening agent,4-(1-phenethyl)-1,3-benzenediol was prepared by catalytic synthesis with styrene and resorcinol as starting materials.The catalyst,silicon supported phosphotungstic acid was prepared by pickling process and characterized by IR,XRD and SEM.The synthesized crude product was purified by re-crystallization in xylene as solvent;and structure of the product was identified by MS and 1H NMR.Its skin-whitening activity and antioxidation activity were evaluated by using tyrosinase activity inhibition test,Fe3+ reducing capacity test as well as free radical inhibition test.Results showed that,the IC50 of the tyrosinase inhibition of the product is 0.010 5 g/L,which is much smaller than that of β-arbutin (IC50=0.64 g/L),and it means that the skin-whitening capacity of the product is conspicuously stronger than that of β-arbutin.Similarly,the EC50 of the capacity for Fe3+ reduction is 0.033 g/L;the EC50 of the capacity for hydroxyl free radical removal is 0.06 g/L;the EC50 of the capacity for superoxide free radical removal is 0.32 g/L;results indicates that the capacity for Fe3+ reduction and superoxide free radical removal of the product are stronger than that of β-arbutin.
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