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
| Autor: | Peter Winterhalter, Ulrich Fischer, Hans-Georg Schmarr, Pia Bechtloff, Michael Ziegler, Recep Gök |
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| Rok vydání: | 2019 |
| Předmět: |
0106 biological sciences
Indicator Dilution Techniques Wine Naphthalenes Mass spectrometry 01 natural sciences Stable isotope dilution Gas Chromatography-Mass Spectrometry Isomerism Vitis Sample preparation Deuterium labeled Aroma Chromatography biology Chemistry 010401 analytical chemistry Vitispiranes General Chemistry Deuterium biology.organism_classification Quantitative determination 0104 chemical sciences Norisoprenoids General Agricultural and Biological Sciences 010606 plant biology & botany |
| Zdroj: | Journal of Agricultural and Food Chemistry. 67:6414-6422 |
| ISSN: | 1520-5118 0021-8561 |
| DOI: | 10.1021/acs.jafc.9b01428 |
| Popis: | 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). |
| Databáze: | OpenAIRE |
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