A mechanistic investigation of H/D scrambling processes in flavonoids

1,1,6-Trimethyl-1,2-dihydronaphthalene (TDN) is a controversial aroma component found in Riesling wines. It belongs to the family of C13-norisoprenoids and is mainly associated with kerosene/petrol notes. TDN can add complexity to the wine aroma at medium – low concentrations and deteriorate the wine bouquet when its content is high. No TDN aromas are usually perceived in young Riesling wines, but they can appear after several years of aging due to the gradual formation of TDN. Management of TDN in Riesling wines is an actual task, since global warming can promote formation of this compound and compromise the aromatic composition of wine. Therefore, the aim of the current work was, firstly, to study the sensory particularities of TDN in Riesling wine at various concentrations. Secondly, to investigate the ability of bottle closures to absorb (scalp) TDN from Riesling wine under various storage conditions. These studies also include the comparative assessment of our findings with previously published data. METHODS: sensory analysis, GC-MS (SBSE), HPLC,1H-NMR and other methods related to the synthesis and determination of TDN. RESULTS: First of all, the method of the synthesis of highly purified TDN (95% and 99.5%) was optimized [1].

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