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研究生： 朱祐萱
Chu, Yu-Hsuan
論文名稱： 高效能液相層析儀搭配2,4-二硝基苯肼衍生法量測米酒中的脂肪醛
Determination of linear aliphatic aldehydes in rice wines by high-performance liquid chromatography using 2,4-dinitrophenylhydrazine derivatization
指導教授： 吳劍侯
Wu, Chien-Hou
口試委員: 吳淑褓
Wu, Shu-Pao
蔡詩偉
Tsai, Shin-Wei
學位類別： 碩士
Master
系所名稱： 原子科學院 - 生醫工程與環境科學系
Department of Biomedical Engineering and Environmental Sciences
論文出版年： 2017
畢業學年度： 105
語文別： 中文
論文頁數： 78
中文關鍵詞： DNPH 、米酒 、醛 、乙醇
外文關鍵詞： DNPH, rice wine, aldehyde, alcohol
相關次數： 點閱：2  下載：0 
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    • 酒中醛類主要的來源為發酵步驟，發酵過程中所選用的原料、酵母菌以及不同的發酵階段和設定參數，皆會影響酒中醛類的濃度，過量的醛類對人體有不良影響，因此有效的監控酒中醛類的含量是十分重要的。本研究利用DNPH (2,4-dinitrophenylhydrazine) 衍生法搭配HPLC-UV量測米酒中的醛，並藉由改變酸濃度、DNPH濃度探討乙醇對衍生反應的影響。由衍生反應的反應速率常數及平衡常數探討，對此反應有更進一步的了解。為了排除乙醇在衍生反應中生成乙醛的可能性，實驗中利用兩種不同酒精依不同比例配製成相同濃度的酒精溶液，探討其乙醛含量的變化。實驗結果顯示乙醇在本研究的分析條件下僅影響衍生時間，並不會氧化成乙醛。此方法也成功應用到真實樣品中醛類的量測與定量。真實樣品中測得的乙醛含量範圍落在360-2304 uM之間。本研究也針對酒及酒糟中的胺基酸含量做初步的定量，結果顯示酒糟中的胺基酸含量比酒中的多2到4個數量級。

    Aldehydes occur in rice wines and most of them arise in fermentation, which can be varied by raw material, species of yeasts, fermentation stages, and different processes. Aldehydes exhibit adverse health effects to human beings. Therefore, it is important to improve the quality of rice wine by monitoring the concentrations of aldehydes in the production line. In this method, aldehydes in rice wines were derivatized with 2,4-dinitrophenylhydrazine (DNPH) and analyzed by HPLC with UV detector. The effect of alcohol content on the derivatization reaction was studied by varying concentrations of HCl and DNPH. The derivatization reactions were investigated to obtain the rate constants and equilibrium constants. In order to exclude the possible formation of acetaldehyde from derivatization, acetaldehyde concentration in 40% alcohol by mixing two different alcohol sources was investigated. The results confirmed that the derivatization reaction would not oxidize alcohol to acetaldehyde and the existence of alcohol would only affect the derivatization rate. This method has been successfully applied to determine the concentration of acetaldehyde in rice wines. Concentrations of acetaldehyde in rice wines were in the range of 360-2304 uM. Amino acids in rice wine and wine lees were also investigated in the study. In our analysis, the amounts of amino acids in wine lees were approximately 2 to 4 order of magnitude more than those in rice wines.

    目錄 中文摘要 I 英文摘要 II 謝誌 III 目錄 IV 圖目錄 V 表目錄 VII 第一章 前言 1 1.1 簡介 1 1.2 研究動機 1 第二章 文獻回顧 2 2.1 酒中的醛類及其來源 2 2.2 乙醛 3 2.2.1 乙醛在日常生活中的來源 3 2.2.2 人體暴露於乙醛的主要途徑 5 2.2.3 酒中的乙醛 6 2.2.4 乙醛的毒性 8 2.3 醛的量測方法 10 2.4 醛與DNPH 13 第三章 實驗方法 17 3.1 實驗裝置 17 3.1.1 高效能液相層析儀 17 3.1.2 其他儀器 18 3.2 實驗藥品 18 3.2.1 母液配製 19 3.3 真實樣品 21 3.4 分析流程 21 3.4.1 樣品溶劑配製方法 21 3.4.2 醛的分析流程 22 3.4.3 真實樣品的分析流程 23 3.5 實驗流程圖 27 第四章 結果與討論 28 4.1 標準品配製方法的探討 28 4.2 乙醇對DNPH衍生反應的影響 35 4.2.1 改變比例 36 4.2.2 改變酸濃度 37 4.2.3 改變DNPH濃度 38 4.2.4 反應速率常數 42 4.2.5 反應平衡常數 46 4.3 真實樣品量測 49 第五章 結論 58 第六章 未來展望 58 參考文獻 59 附錄1 常用溶劑性質表 64 附錄2 不同樣品溶劑之醛檢量線 65 附錄3 反應速率常數計算 66 附錄4 胺基酸檢量線 72 圖目錄 Fig. 2-1. Polymerization of polyethylene terephthalate 5 Fig. 2-2. Production process of rice wines 6 Fig. 2-3. Ethanol and acetaldehyde metabolism. 9 Fig. 2-4. DNPH derivatization 10 Fig. 2-5. PFBHA derivatization. 11 Fig. 2-6. Nash’s reaction. 11 Fig. 2-7. Mechanism for the formation of hydrazone in basic environment. 14 Fig. 2-8. Mechanism for the formation of hydrazone in acidic environment. 15 Fig. 2-9. Derivatization reaction of OPA/2-ME and amino acid. 16 Fig. 3-1. High Performance Liquid Chromatography (HPLC) 17 Fig. 3-2. Gradient elution program of HPLC-UV/vis for determining aldehydes. 20 Fig. 3-3. Chromatographic profile of nine aldehydes and acetone derivatized with DNPH for 30 min at pH 1.8. 22 Fig. 3-4. Chromatographic profile of ten amino acids. 26 Fig. 4-1. Change of peak area of nine aliphatic aldehydes after derivatization in different proportion of sample solvent. 29 Fig. 4-2. Chromatographic profile of nine aliphatic aldehydes derivatized with DNPH in different proportion of sample solvent. 29 Fig. 4-3. Chromatographic profile of different proportion of sample solvent derivatized with DNPH.. 30 Fig. 4-4. Definition of asymmetry factor. 31 Fig. 4-5. Asymmetry factor of peaks of nine aldehydes derivatized with DNPH in different proportion of sample solvent.. 32 Fig. 4-6. The relationship between limit of blank and sample solvent. 34 Fig. 4-7. Acetaldehyde impurities as function of alcohol-by-volume (%) in regular and absolute alcohols. 35 Fig. 4-8. Total concentration of acetaldehyde in 40% alcohol with the combination of 95% (regular alcohol, solvent A) and 99.8% (absolute alcohol, solvent B) 36 Fig. 4-9. Effect of different HCl concentration on peak area of acetaldehyde derivatized with DNPH in ethanol.. 38 Fig. 4-10. Effect of DNPH concentration on peak area of acetaldehyde derivatized with DNPH in 20% ethanol. 39 Fig. 4-11. Effect of DNPH concentration on peak area of acetaldehyde derivatized with DNPH in 40% ethanol.. 40 Fig. 4-12. Effect of DNPH concentration on peak area of acetaldehyde derivatized with DNPH in 60% ethanol. 40 Fig. 4-13. Effect of different DNPH concentration on concentration of acetaldehyde derivatized with DNPH in 20%, 40%, 60% ethanol and 10 M acetaldehyde in DIW. 41 Fig. 4-14. Effect of different DNPH concentration on concentration of acetaldehyde in DIW. 41 Fig. 4-15. Effect of DNPH concentration on the concentration of acetaldehyde in ethanol.. 42 Fig. 4-16. Investigation about rate constant of first order in 60% alcohol at room temperature. 43 Fig. 4-17. Rate constant (k’) as function of the concentration of DNPH. 44 Fig. 4-18. The relationship between rate constant and concentration of ethanol. 46 Fig. 4-19. Reciprocal hydrazone response of different ethanol concentration and acetaldehyde in DIW as function of reciprocal DNPH concentration. 48 Fig. 4-20. HPLC-UV chromatograms of rice wines. Dilute factor = 2 51 Fig. 4-21. HPLC-UV chromatograms of rice wines. Dilute factor = 1000 52 Fig. 4-22. Concentration of acetaldehyde in rice wines with storage time. 52 Fig. 4-23. Comparison of acetaldehyde concentration in real samples. 53 Fig. 4-24. HPLC-FL chromatogram of sample 1. 55 Fig. 4-25. HPLC-FL chromatogram of sample 2. 55 Fig. 4-26. HPLC-FL chromatogram of sample 3. 56 Fig. 4-27. HPLC-FL chromatogram of wine lees. 57 Fig. S-1. Calibration curves of formaldehdye, acetaldehyde, and propanal. Conditions: sample solvent = 0% acetonitrile 66 Fig. S-2. Calibration curves of butanal, pentanal, and hexanal. 67 Fig. S-3. Calibration curves of heptanal, octanal, and nonanal. 67 Fig. S-4. Calibration curves of formaldehdye, acetaldehyde, and propanal. Conditions: sample solvent = 50% acetonitrile 68 Fig. S-5. Calibration curves of butanal, pentanal, and hexanal.. 69 Fig. S-6. Calibration curves of heptanal, octanal, and nonanal.. 69 Fig. S-7. Calibration curves of formaldehdye, acetaldehyde, and propanal. Conditions: sample solvent = 100% acetonitrile 70 Fig. S-8. Calibration curves of butanal, pentanal, and hexanal. 71 Fig. S-9. Calibration curves of heptanal, octanal, and nonanal. 71 Fig. S-10. Investigation about rate constant of second order in 60% alcohol. 72 Fig. S-11. The relationship between peak area and derivatization time of DNPH reaction with acetaldehyde in DIW 72 Fig. S-12. Investigation about rate constant of first order in 20%, 40% alcohol, and 25 M acetaldehyde in DIW. 73 Fig. S-13. Calibration curve of Asp. 74 Fig. S-14. Calibration curve of Glu. 74 Fig. S-15. Calibration curve of Ser. 75 Fig. S-16. Calibration curve of Arg. 75 Fig. S-17. Calibration curve of Gly. 76 Fig. S-18. Calibration curve of Thr. 76 Fig. S-19. Calibration curve of Ala. 77 Fig. S-20. Calibration curve of GABA. 77 Fig. S-21. Calibration curve of Val. 78 Fig. S-22. Calibration curve of Phe. 78 表目錄 Table 2-1. Acetaldehyde levels in alcoholic beverages. 3 Table 2-2. Flavor characteristics of volatile, short chain aldehydes. 4 Table 2-3. Acetaldehyde levels produced by yeast. 7 Table 2-4. Comparison of different derivatization methods for the determination of aldehydes in water samples. 12 Table 2-5. Melting point and color of different DNPH derivatives. 13 Table 3-1. Properties of chemicals and reagents. 20 Table 3-2. Gradient elution program of HPLC-FL for determining amino acids. 24 Table 4-1. Calibration curves of nine aliphatic aldehydes. Sample solvent: 0% acetonitrile. 33 Table 4-2. Calibration curves of nine aliphatic aldehydes. Sample solvent: 50% acetonitrile. 33 Table 4-3. Calibration curves of nine aliphatic aldehydes. Sample solvent: 100% acetonitrile. 34 Table 4-4. Summary of k’ and DNPH concentration 44 Table 4-5. Rate constant of acetaldehyde derivatized with DNPH in DIW and 20%, 40%, 60% ethanol at room temperature. 45 Table 4-6. Equilibrium constant of acetaldehyde derivatized with DNPH in DIW and 20%, 40%, 60% ethanol. 48 Table 4-7. Concentration of acetaldehyde in real sample. 51 Table 4-8. Concentration of acetaldehyde in real samples. 53 Table 4-9. Concentration of amino acids in rice wines 56 Table 4-10. Concentration of amino acids in wine lees. 57

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