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    Please use this identifier to cite or link to this item: http://ir.cnu.edu.tw/handle/310902800/24505


    標題: 合成羥基取代之桂皮酸苯乙酯衍生物探討其有效性於化粧品之應用
    Studies on Synthesis of Hydroxy Substituted 2-Phenylethylcinnamate Derivatives as Their Efficiency on Cosmetic Application
    作者: 黃仲挺
    貢獻者: 嘉南藥理科技大學:化妝品科技研究所
    楊朝成
    關鍵字: 有機合成
    羥基取代之桂皮酸苯乙酯
    抗氧化
    美白
    紫外線吸收
    UV absorbing
    anti-oxidant
    hydroxy substituted cinnamate
    organic synthesis
    日期: 2011
    上傳時間: 2011-10-25 13:28:15 (UTC+8)
    摘要: 本研究主要利用有機合成的方法,將不同數量、位置的羥基取代之桂皮酸化合物(或羥基苯甲酸)與苯乙醇(或對-羥基苯乙醇)進行酯化反應後,得到一系列的羥基取代之桂皮酸苯乙酯衍生物 (化合物1~16),再透過6種不同活性試驗方法來探討其有效性及安全性:一、清除DPPH自由基能力試驗;二、TEAC總抗氧化能力試驗;三、抑制酪胺酸酶活性試驗;四、紫外線吸收測試;五、抑制MMPs活性試驗;六、MTT細胞毒性測試,且分別以水溶性維生素E、維生素C、麴酸及Parsol MCX作為對照組,探討本實驗化合物活性之優劣與應用於化粧品之可行性。
    根據實驗結果,羥基取代之桂皮酸苯乙酯衍生物在各項活性試驗中皆具有不錯的表現;其中以Compounds 4、10最為優異,同時在抗氧化(清除DPPH自由基能力之IC50 = 8.63~9.10 μg/ml,對照組Trolox之IC50 = 9.94 μg/ml;TEAC總抗氧化能力之IC50 = 2.35~4.64 μg/ml,對照組Trolox之IC50 = 5.17 μg/ml)、美白(抑制酪胺酸酶活性之IC50 = 49.48~56.98 μg/ml,對照組Vit.C之IC50 = 78.05 μg/ml)及紫外線吸收(ε = 60.1~67.6 L/g*cm,對照組Parsol MCX之ε = 55.4 L/g*cm)都有不錯的效果;而Compound 3、9在美白方面具有不錯的效果(抑制酪胺酸酶活性之IC50 = 35.20~45.15 μg/ml),亦具有不錯的紫外線吸收能力(ε = 56.2~64.9 L/g*cm);另外,Compound 14在美白能力上效果極佳(抑制酪胺酸酶活性之IC50 = 29.70 μg/ml,對照組kojic acid之IC50 = 23.99 μg/ml),且抗氧化能力在本實驗之化合物中也名列前茅(清除DPPH自由基能力之IC50 = 6.88 μg/ml;TEAC總抗氧化能力之IC50 = 2.90 μg/ml);Compounds 5、6、11、12具有寬且廣的紫外線吸收範圍(ε = 57.4~72.1 L/g*cm),尤其偏重在對於人體傷害較大的UVA波長範圍。
    而在細胞毒性方面,大部分實驗的化合物對於細胞的傷害並不高,因此本實驗所合成的羥基取代之桂皮酸苯乙酯衍生物在應用於化粧品之抗氧化、美白及防曬等機能上,極具開發潛力。
    This research utilized the method of organic synthesis, to synthesize a series of polyhydroxy substituted phenylethylcinnamate derivatives (compounds 1~16), by the esterification as different amounts and different positions of hydroxy-substitued cinnamic acids (or benzoic acids) with 2-phenylethyl alcohol (or 2-(4-hydroxyphenyl)ethanol).
    After that, we used six types of activity test to study their efficiencies and safety on cosmetic application:I. The antioxidant activity of scavenge DPPH free radical; II. The ability of overall antioxidant— the activity of TEAC; III. The activity test of inhibit Tyrosinase, IV. To study of UV absorbing test; V. The activity test of inhibit matrix metallopteinases (MMPs); VI. Cell viability was determined by MTT assay. Furthermore, we used trolox, ascorbic acid, kojic acid and Parsol MCX as the control groups for the activity test, respectively.
    The result of our study, the hydroxy substituted cinnamate derivatives had the great efficiency on all of the test. Furthermore, compounds 4、10 had the most excellent ability, they had great activity on anti-oxidant (on scavenge DPPH free radical assay, IC50 = 8.63~9.10 μg/ml; Trolox, IC50 = 9.94 μg/ml; on overall antioxidant— the activity of TEAC assay, IC50 = 2.35~4.64 μg/ml; Trolox, IC50 = 5.17 μg/ml), whitening (on inhibit tyrosinase activity assay, IC50 = 49.48~56.98 μg/ml; Vit.C, IC50 = 78.05 μg/ml) and UV absorbing (ε = 60.1~67.6 L/g*cm; Parsol MCX, ε = 55.4 L/g*cm). And compounds 3、9 had great activity on whitening (on inhibit tyrosinase activity assay, IC50 = 35.20~45.15 μg/ml) and UV absorbing (ε = 56.2~64.9 L/g*cm). And compounds 14 had great activity on whitening (on inhibit tyrosinase activity assay, IC50 = 29.70 μg/ml; Kojic acid, IC50 = 23.99 μg/ml) and anti-oxidant (on scavenge DPPH free radical assay, IC50 = 6.88 μg/ml; on overall antioxidant— the activity of TEAC assay, IC50 = 2.90 μg/ml). And Compounds 5、6、11、12 had widely UV absorb range (ε = 57.4~72.1 L/g*cm L/g*cm), especially focus on UVA that can cause biggest harm to the human body.
    On the Cell viability test, most of the compounds on our study hadn’t cytotoxic. Therefore that, the hydroxy substituted cinnamate derivatives on our study have the development potential as the anti-oxidant, whitening and sun protection of cosmetic.
    Appears in Collections:[化妝品應用與管理系(所)] 博碩士論文

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