手性香料香芹酮和乙酸苏合香酯的液相色谱拆分及其对映体纯度测定

Liquid Chromatographic Resolution and Determination of Enantiomeric Purity of Chiral Flavors Carvone and Styrallyl Acetate

香芹酮和乙酸苏合香酯是2种重要的食品用手性香料,它们的香味特征与其对映体构型及对映体含量有关.因此,对这类手性香料进行色谱拆分不仅在分析鉴定香料、开发食用香精配方、食品分析,而且在香料科学的基础研究方面也具有重要的意义.本研究采用新型的直链淀粉-三((S)-α-甲基苯基氨基甲酸酯)手性固定相(Chiralpak AS-H柱),系统考察了香芹酮、乙酸苏合香酯对映体的液相色谱拆分行为.实验表明:在该手性柱上,采用正己烷-异丙醇(体积比为95∶5)流动相,在10min内,香芹酮和乙酸苏合香酯对映体即可获得很好的基线分离,分离度分别达到2.49和2.86;手性色谱分离为焓驱动过程;手性固定相侧链中α-甲基苯基手性中心可能对香芹酮的手性识别起到增强的作用.所建立的色谱分析方法准确、可靠、简便,可用于实际香料样品的对映体纯度分析.

Carvone and styrallyl acetate are two important chiral flavors in food additives.Their fragrance is related to their configurations and enantiomeric ratios.Therefore,the enantioseparation of these flavors is helpful to identify flavors and to develop flavor formula for food industry.In addition it is important in basic research of flavor science.In this paper,the high performance liquid chromatography enantioseparation of chiral carvone and styrallyl acetate was studied using amylose tris-（S）-α-methylbenzylcarbamate as the chiral stationary phase（Chiralpak AS-H column）.The effects of alcohol content in the mobile phase and column temperature on the retention and enantioseparation were investigated.Additionally,the chiral recognition mechanism between the analytes and the chiral stationary phase（CSP）was discussed.The results show that baseline enantioseparations of carvone and styrallyl acetate are easily obtained in 10 min on that column with a mobile phase of n-hexane-isopropanol（95∶5,by vol.）at a flow rate of 1.0mL/min under 30 ℃.The（R）-isomers are first eluted and the enantioseparation is typically enthalpy-controlled.The chiral center ofα-methylbenzyl on CSP may strengthen the chiral recognition of carvone.The method established is simple,reliable and accurate,and has been successfully applied to determine enantiomeric purity of optical flavor samples.