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Synthesis of Deuterium-Labeled 1,1,6-Trimethyl-1,2-dihydronaphthalene (TDN) and Quantitative Determination of TDN and Isomeric Vitispiranes in Riesling Wines by a Stable-Isotope-Dilution Assay
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2019-05-15 00:00:00 , DOI: 10.1021/acs.jafc.9b01428 Recep Gök 1 , Pia Bechtloff 1 , Michael Ziegler 2 , Hans-Georg Schmarr 2 , Ulrich Fischer 2 , Peter Winterhalter 1
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2019-05-15 00:00:00 , DOI: 10.1021/acs.jafc.9b01428 Recep Gök 1 , Pia Bechtloff 1 , Michael Ziegler 2 , Hans-Georg Schmarr 2 , Ulrich Fischer 2 , Peter Winterhalter 1
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The C13-norisoprenoid aroma compounds 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN) and isomeric 2,10,10-trimethyl-6-methylene-1-oxaspiro[4.5]dec-7-enes, so-called vitispiranes, are considered to be biosynthetically related. They occur at higher concentrations in bottle-aged Riesling wines especially and are important contributors to the varietal aroma of Riesling wines. Because of the variation of the quantitative methods and data reported in the literature, a redetermination of concentration levels for both free and total TDN and isomeric vitispiranes, especially in German Riesling wines, was performed using a stable-isotope-dilution assay (SIDA). For this purpose, a novel six-step synthetic route to TDN and deuterium-labeled TDN was developed. A standardized sample preparation for TDN and vitispiranes and a rapid acid-hydrolysis method at genuine wine-pH conditions for the conversion of the precursors into TDN and vitispiranes were also developed. Automated HS-SPME was applied to 250 wine samples from two wine competitions, and analysis was performed by gas chromatography–mass spectrometry with selected-ion monitoring (GC-SIM-MS) as well as selected-reaction monitoring (GC-SRM-MS).
中文翻译：
稳定同位素稀释法测定氘标记的1,1,6-三甲基1,2-二氢萘（TDN）并定量测定雷司令葡萄酒中的TDN和异维他螺烷
C 13-norisoprenoid芳香族化合物1,1,6-三甲基-1,2-二氢萘（TDN）和异构体2,10,10-三甲基-6-亚甲基-1-氧杂螺[4.5] dec-7-enes，所谓的vitispiranes被认为与生物合成有关。它们在瓶装雷司令葡萄酒中的浓度较高，尤其是雷司令葡萄酒的品种香气的重要贡献者。由于文献中报道的定量方法和数据存在差异，因此使用稳定的同位素稀释测定法（SIDA）对游离TDN和总TDN以及异构体维斯匹兰的浓度水平进行了重新测定，尤其是在德国雷司令葡萄酒中。为了这个目的，开发了一种新颖的六步合成途径来合成TDN和氘标记的TDN。还开发了用于TDN和维替斯潘烷的标准化样品制备方法，以及在纯正的葡萄酒pH条件下将前体转化为TDN和维斯替潘烷的快速酸水解方法。自动化的HS-SPME应用于来自两个葡萄酒比赛的250个葡萄酒样品，并通过气相色谱-质谱联用选择离子监测（GC-SIM-MS）和选择反应监测（GC-SRM-MS）进行分析）。
更新日期：2019-05-15
中文翻译：
稳定同位素稀释法测定氘标记的1,1,6-三甲基1,2-二氢萘（TDN）并定量测定雷司令葡萄酒中的TDN和异维他螺烷
C 13-norisoprenoid芳香族化合物1,1,6-三甲基-1,2-二氢萘（TDN）和异构体2,10,10-三甲基-6-亚甲基-1-氧杂螺[4.5] dec-7-enes，所谓的vitispiranes被认为与生物合成有关。它们在瓶装雷司令葡萄酒中的浓度较高，尤其是雷司令葡萄酒的品种香气的重要贡献者。由于文献中报道的定量方法和数据存在差异，因此使用稳定的同位素稀释测定法（SIDA）对游离TDN和总TDN以及异构体维斯匹兰的浓度水平进行了重新测定，尤其是在德国雷司令葡萄酒中。为了这个目的，开发了一种新颖的六步合成途径来合成TDN和氘标记的TDN。还开发了用于TDN和维替斯潘烷的标准化样品制备方法，以及在纯正的葡萄酒pH条件下将前体转化为TDN和维斯替潘烷的快速酸水解方法。自动化的HS-SPME应用于来自两个葡萄酒比赛的250个葡萄酒样品，并通过气相色谱-质谱联用选择离子监测（GC-SIM-MS）和选择反应监测（GC-SRM-MS）进行分析）。
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