羥基取代之桂皮酸苯乙酯衍生物合成並探討其抗氧化能力與應用於化粧品之安全性

Studies on Synthesis of Hydroxyl Substituted 2-Phenylethylcinnamate Derivatives as Their Anti-oxidation on Cosmetic Application

本研究是以羥基不同位置與數量取代的桂皮酸化合物與苯乙醇進行酯化反應，得一系列羥基不同位置與數量取代的桂皮酸苯乙酯衍生物；並以維生素E為對照組，進行一系列試驗：一、清除DPPH自由基能力試驗，二、TEAC總抗氧化能力試驗，三、MTT細胞毒性等三種測試，以評估其抗氧化能力與安全性測試及未來應用於化粧品上之可行性。結果發現：抗氧化能力與桂皮酸苯環上羥基取代的數量與位置有關，雙取代羥基比單取代強，其中羥基在桂皮酸苯環上與羰基成對位（R3）時可增強其抗氧化能力，當羥基被甲氧基取代時會降低抗氧化能力，尤其是發生在R3時更為顯著，顯示在桂皮酸苯環上與羰基成對位的羥基，在抗氧化上扮演相當重要的角色。在細胞毒性試驗上，所有化合物在有效濃度下，對細胞毒害皆相當低，深具安全性。故本實驗中合成的羥基取代之桂皮酸苯乙酯衍生物未來應用於化粧品的抗氧化功能上極具開發潛力。

The study uses cinnamic acid substituted with different positions and amounts of hydroxyl and 2-phenylehtanol to conduct esterifications. Then we gain a series of 2-phenylethylcinnamate derivatives （compound 1a/b-8a/b） of different positions and amounts of hydroxyl. Then as vitamin E as a comparison and conducted a series of experiments: First, the experiments of scavenging DPPH free radicals, second, the experiments of the efficiency of anti-oxidation of TEAC and third, the experiments of toxicity of the cells of MTT. The three experiments are aimed to assess the efficiency of anti-oxidation, and safety testings and the possibility of applying on cosmetics in the future.It is found that the efficiency of anti-oxidation is related with the amounts and positions of hydroxyl-substituted on 2-phenylethylcinnamate derivatives. The efficiency is stronger when there is two-substituted of hydroxyl groups than monosubstituted, hydroxyl-substituted plays an important role during the action especially when hydroxyl-substituted is attached to para position on phenyl of cinnamic acid. However, the efficiency goes down when it is substituted by methoxyl rather than hydroxyl group especially in the R3 position. Additionally, under effective concentration, all compounds reveal high safety and low toxicity to cells in. Therefore, the 2-phenylethylcinnamate derivatives that is substituted by hydroxyl is full of potential on the development of the efficiency of anti-oxidationto in cosmetics in the future.