Roling I, Schmarr HG, Eisenreich W, Engel KH
Technische Universität München, Lehrstuhl für Allgemeine Lebensmitteltechnologie, Am Forum 2, D-85350 Freising-Weihenstephan, Germany, and Technische Universität München, Lehrstuhl für Organische Chemie und Biochemie, Lichtenbergstrasse 4, D-85748 Garching, Germany.
J Agric Food Chem. 1998 Feb 16;46(2):668-672. doi: 10.1021/jf970748+.
gamma-Thiolactones [5-alkyldihydro-2(3H)-thiophenones] and delta-thiolactones (6-alkyltetrahydro-2H-thiopyran-2-ones) were synthesized via isothiouronium salts by reaction of the corresponding oxygen-containing lactones with thiourea and hydrobromic acid. The identity of the compounds was confirmed by means of IR, MS, and (1)H and (13)C NMR. Separation of the enantiomers of the thiolactones was achieved by capillary GC using heptakis(2,3-di-O-methyl-6-O-TBDMS)-beta-cyclodextrin as stationary phase. The substitution of oxygen by sulfur induces tropical fruit notes, which are more pronounced for the delta-thiolactones. Odor thresholds are dependent on ring size and chain length.
γ-硫代内酯[5-烷基二氢-2(3H)-噻吩酮]和δ-硫代内酯(6-烷基四氢-2H-硫代吡喃-2-酮)通过相应的含氧内酯与硫脲和氢溴酸反应，经由异硫脲盐合成。通过红外光谱、质谱以及氢核磁共振和碳核磁共振确认了化合物的结构。使用七(2,3-二-O-甲基-6-O-TBDMS)-β-环糊精作为固定相，通过毛细管气相色谱法实现了硫代内酯对映体的分离。用硫取代氧会产生热带水果香气，对于δ-硫代内酯来说更为明显。气味阈值取决于环大小和链长度。
Zotero 插件