Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Science and Technology, Wyb. Wyspiańskiego 27, 50-370 Wrocław, Poland.
Institute of General Food Chemistry, Faculty of Biotechnology and Food Sciences, Technical University of Łódź, Żeromskiego 116, 90-924 Łódź, Poland.
Food Chem. 2019 Dec 15;301:125283. doi: 10.1016/j.foodchem.2019.125283. Epub 2019 Jul 29.
A small library of 57 low molecular weight oximes was prepared from fragrant aldehydes and ketones, and their olfactory profiles were determined. The most substantive and interesting in terms of the sensory impressions were (+)-isomenthone oxime (fresh, musty, green) and cyclocitral oxime (earthy with patchouli, moss and leather notes). The linear retention indices (LRI) were determined for DB-1, DB-5 and DB-WAX columns, and E/Z isomers of 22 out of 57 compounds were resolved on the DB-5 column. Attempts were made to resolve enantiomers of the chosen oximes on chiral GC columns. The best results were obtained by using a Cyclosil B column, on which the enantiomers of camphor, menthone, piperitone and carvone oximes were fully resolved. NMR and MS spectra were acquired to characterize the synthesized library. Gas chromatography-olfactometry was used to assess odoriferous properties of both isomers of oximes. In most cases both isomers possessed similar profile and intensity.
从芳香醛和酮中制备了一个包含 57 个低分子量肟的小库，并确定了它们的气味特征。就感官印象而言，最实质性和有趣的是（+）-异薄荷酮肟（新鲜，发霉，绿色）和环柠檬醛肟（泥土味，带有广藿香，苔藓和皮革味）。确定了 DB-1、DB-5 和 DB-WAX 柱的线性保留指数（LRI），并在 DB-5 柱上分离了 57 种化合物中的 22 种 E/Z 异构体。尝试在手性 GC 柱上拆分所选肟的对映异构体。使用 Cyclosil B 柱获得了最佳结果，在此柱上完全拆分了樟脑、薄荷酮、胡椒酮和香芹酮肟的对映异构体。获得了 NMR 和 MS 光谱以表征合成库。气相色谱-嗅觉评估了肟的两种异构体的气味特性。在大多数情况下，两种异构体都具有相似的特征和强度。
