A number of polyfunctional thiols are well-recognised as some of the most potent aroma compounds in nature and have been identified in various foods, and beverages such as wine. These potent character impact compounds are present at nanogram-per-litre levels and are particularly challenging to measure. Where present, enantiomeric forms having different odour qualities further complicate the analysis. In this work, a chiral high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) method using stable isotope dilution analysis (SIDA) has been developed and validated for the individual enantiomers of 3-sulfanylhexan-1-ol (3-SH, 1) and its O-acetate, 3-sulfanylhexyl acetate (3-SHA, 2), in wine after extraction as their 4-thiopyridine derivatives. Authentic derivatised thiols were first synthesised and used for chiral column screening and method development with polysaccharide-based HPLC phases. Validation of the method using a Lux Amylose-1 column for quantification of the enantiomers of 1 and 2 gave linear calibrations, and excellent figures for accuracy (recovery: 90%-111%, Z-score: -1.8-1.9), precision (RSDr<8%), and limits of detection (0.7 ng L-1 or less) in model media and different wine matrices. The newly developed method was applied to determine the enantiomer profiles of 1 and 2 in range of commercial wines.

中文翻译：

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用高效液相色谱-串联质谱法手性分析葡萄酒中的 3-硫基己基-1-醇和 3-硫基己基乙酸酯

许多多功能硫醇被公认为自然界中一些最有效的芳香化合物，并已在各种食品和饮料（如葡萄酒）中得到鉴定。这些有效的影响性格的化合物以每升纳克的水平存在，并且特别难以测量。如果存在，具有不同气味品质的对映体形式进一步使分析复杂化。在这项工作中，开发了一种使用稳定同位素稀释分析 (SIDA) 的手性高效液相色谱-串联质谱 (HPLC-MS/MS) 方法并验证了 3-硫烷基己基-1-醇的各个对映异构体 (3 -SH, 1) 及其 O-乙酸酯，3-硫烷基己基乙酸酯 (3-SHA, 2)，提取后作为其 4-硫代吡啶衍生物在葡萄酒中。真正的衍生硫醇首先被合成并用于手性柱筛选和基于多糖的 HPLC 固定相的方法开发。使用 Lux Amylose-1 色谱柱对 1 和 2 的对映异构体进行定量验证该方法得到了线性校准，以及出色的准确度数据（回收率：90%-111%，Z 分数：-1.8-1.9） RSDr<8%），以及模型培养基和不同葡萄酒基质中的检测限（0.7 ng L-1 或更低）。新开发的方法用于确定商业葡萄酒范围内 1 和 2 的对映异构体特征。模型培养基和不同葡萄酒基质中的精密度 (RSDr<8%) 和检测限（0.7 ng L-1 或更低）。新开发的方法用于确定商业葡萄酒范围内 1 和 2 的对映异构体特征。模型培养基和不同葡萄酒基质中的精密度 (RSDr<8%) 和检测限（0.7 ng L-1 或更低）。新开发的方法用于确定商业葡萄酒范围内 1 和 2 的对映异构体特征。