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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
- Source :
- Journal of Agricultural and Food Chemistry. 67:6414-6422
- Publication Year :
- 2019
- Publisher :
- American Chemical Society (ACS), 2019.
-
Abstract
- 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).
- Subjects :
- 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
Subjects
Details
- ISSN :
- 15205118 and 00218561
- Volume :
- 67
- Database :
- OpenAIRE
- Journal :
- Journal of Agricultural and Food Chemistry
- Accession number :
- edsair.doi.dedup.....390a0f67da3c611474f48e3918029cee