导　　师： 晏日安

学科专业： 083201

授予学位： 硕士

作　　者： ;

机构地区： 暨南大学

摘　　要： 首先，研究了超声处理，减压条件下合成蔗糖月桂酸酯，采用薄层层析（TLC）和硅胶柱层析对产物进行分离纯化，并对纯化后的组分通过红外光谱（IR），质谱（MS），高效液相（HPLC）及核磁共振（1H-NMR、13C-NMR）进行结构鉴定。TLC分离蔗糖月桂酸酯的较佳条件：点样量4μL，以氯仿//甲醇//冰乙酸//水（75:15:7:3，V//V//V//V）展开25min，然后用10/%磷钼酸乙醇溶液喷雾，105°C显色10min。硅胶柱层析分离蔗糖月桂酸酯的较佳条件为：3g样品溶于10mL洗脱剂，35mm×700mm硅胶（200-300目）层析柱，流动相为TLC展开剂的配比。两种单酯组分分别为6-O-蔗糖月桂酸酯和6’-O-蔗糖月桂酸酯。 其次，研究了超声波处理，减压条件下二甲基亚砜中无水碳酸钾催化棉籽糖和月桂酸甲酯的酯交换反应，通过单因素实验，得到了棉籽糖脂肪酸酯合成的较佳条件为：反应压力为10Kpa，无水K2CO3占棉籽糖的摩尔分数为12/%，棉籽糖//月桂酸甲酯的摩尔比为2:1，反应时间为2h，反应温度为65°C，产率可达44.3/%。对合成的棉籽糖月桂酸酯进行分离纯化，薄层层析（TLC）分离棉籽糖月桂酸酯的较佳条件为：点样量4μL，以氯仿//甲醇//冰乙酸/(V//V//V,75:25:4/)展开10min，用10/%磷钼酸乙醇溶液均匀喷雾后在105°C显色10min。硅胶柱层析分离棉籽糖酯的较佳条件为：1g样品溶于3mL的洗脱剂，过15mm×700mm硅胶（200-300目），流动相的配比与TLC展开剂相同。对纯化后的组分采用高效液相（HPLC），红外光谱（IR），质谱（MS）及核磁共振（1H-NMR、13C-NMR）进行结构鉴定，确定两单酯组分分别为1’-O-棉籽糖月桂酸酯和6’-O-棉籽糖月桂酸酯。同时测定并比较了两种单酯的溶解性和热稳定性，结果表明两种棉籽糖单酯具有相似的溶解性和热稳定性。 再者，研究了α-半乳糖苷酶酶解化学合成的1’-O-棉籽糖月桂酸单酯和6’-O-棉籽糖月桂酸单酯，获得了1’-O-蔗糖月桂酸单酯和6’-O-蔗糖月桂酸单酯。通过单因素实验探讨了α-半乳糖苷酶酶解棉籽糖脂肪酸单酯的条件，选取乙酸-乙酸钠作为酶解反应的缓冲液，酶解反应的较佳条件为：缓冲溶液pH为3.8，酶解时间为48h，酶解温度为37°C。在此条件下，酶解率约为82.6/%。 最后，研究了化学法和化学-酶法获得的蔗糖单酯的溶解性、亲水亲油平衡值（HLB值）、表面张力（CMC值）和热稳定性，结果表明3种蔗糖月桂酸单酯具有相似的溶解性和HLB值，具有相近的表面张力和较高的热稳定性。 Firstly, the lauroylsucrose synthesis under ultrasonic condition was separated, after thatpurified by the thin layer chromatography /(TLC/) and silica gel column chromatography. Purifiedproducts were analyzed by IR, MS, HPLC and NMR. Optimum conditions for TLC wereconfirmed:4μL of the reaction mixture were applied to silica gel G plates, developed bychloroform-methanol-aceticacid-water /(75:15:7:3, V//V//V//V/), and then detected by spraying with10/%of phosphomolybdic acid hydrate in ethanol and heated at105°C for10min. Optimumconditions for silica gel column chromatography were:3g sample dissolved in eluent wasapplied to35mm×700mm silica gel column /(200-300mesh/) and chloroform-methanol-aceticacid-water /(75:15:7:3, V//V//V//V/) was used as mobile phase. Purified products were6-O-lauroylsucrose and6’-O-lauroylsucrose. Furthermore, raffinose long-chain fatty acid esters were synthesized in dimethylsulfoxide bythe acylation of raffinose with methyl laurate under reduced pressure with ultrasound irradiation.Optimum parameters of the reaction were as follows: the reaction pressure was10KPa, thequantity of anhydrous K2CO3was12/%accounted for raffinose’ mol, the molar ratio ofraffinose//methyl laurate was2:1, reaction time was2h, reaction temperature was65°C, and theyield was44.3/%. Optimum conditions for TLC were confirmed:4μL of the reaction mixture wasapplied to silica gel G plates, developed by chloroform-methanol-aceticacid/(V//V//V，75:25:4/),and then detected by spraying with10/%of phosphomolybdic acid hydrate in ethanol and heatedat105°C for10min. Optimum conditions for silica gel column chromatography were:1g sampledissolved in3mL eluent was applied to15mm×700mm silica gel column /(200-300mesh/), andchloroform-methanol-acetic acid was used as mobile phase. Purified products were analyzed byHPLC, IR, MS and NMR, and identified1’-O-lauroylraffinose and6’-O-lauroylraffinose. Thetwo lauroylraffinose isomerides have similar solubility in solvent and higher thermal stability. Next,1’-O-lauroylsucrose and6’-O-lauroylsucrose were formed through hydrolyzingsynthesized1’-O-lauroylraffinose and6’-O-lauroylraffinose by chemical method, respectively, inthe presence of α-galactosidase. The enzymatic hydrolysis of1’-O-lauroylraffinose and6’-O-lauroylraffinose was discussed in detail. Acetic acid-sodium acetate was chosen as thebuffer solution of the enzymatic hydrolysis reaction. Optimum conditions for the enzymatichydrolysis reaction were as follows: buffer solution pH3.8, enzymatic time48h, and enzymatictemperature37°C. Under optimal process conditions, the efficiency of α-galactosidase was ca.82.6/%. Ultimately, isomers were fully compared in solubility, hydrophile-lipophile balance /(HLB/)values, critical micelle concentration /(CMC/), and thermal stability. Results showed that alllauroylsucrose isomers have similar solubility in solvent, HLB values, CMC values, and thermalstability.

关 键 词： 薄层层析 硅胶柱层析 超声处理 蔗糖月桂酸酯 棉籽糖月桂酸酯 半乳糖 苷酶酶 酶解反应 值 表面张力 热稳定性

分 类 号： [TS201.2]

领　　域： [轻工技术与工程] [轻工技术与工程]