Department of Chemistry and Pharmacy, Food Chemistry, Emil Fischer Center, University of Erlangen-Nuremberg, Henkestr. 9, D-91052 Erlangen, (phone: +49-9131-8522739).
Chem Biodivers. 2013 Sep;10(9):1683-95. doi: 10.1002/cbdv.201300097.
The present study aimed at analyzing the odor properties of a group of physiological human metabolites of the odorant 1,8-cineole: 2,3-dehydro-, α2,3-epoxy-, α/β2-hydroxy-, α3-hydroxy-, 4-hydroxy-, 7-hydroxy-, 9-hydroxy-, 2-oxo-, and 3-oxo-1,8-cineole. These metabolites constitute a group of structurally closely related molecules, which differ mainly in nature and position of O-containing functional groups. They thus offer the possibility to correlate odor properties with molecular structure, i.e., to establish structure-odor relationships of compounds that are biologically generated from a potent odorant as parent substance. Generally, the metabolites preserved the eucalyptus-like odor quality of 1,8-cineole but showed additional odor notes such as sweet, citrus-like, plastic-like, earthy, musty, and faecal, which made them distinguishable. The individual enantiomers of chiral molecules also exhibited different odors. With the exception of 2,3-dehydro-1,8-cineole, all metabolites showed a highly decreased odor threshold in comparison to 1,8-cineole. The determination of odor qualities and odor thresholds was accomplished by gas chromatography/olfactometry (GC/O) on achiral and chiral GC capillaries. The results were correlated with common theories on structure-odor relationships.
本研究旨在分析一组生理人体代谢物的气味特性，这些代谢物是气味化合物 1,8-桉树脑的：2,3-脱氢-、α2,3-环氧-、α/β2-羟基-、α3-羟基-、4-羟基-、7-羟基-、9-羟基-、2-氧代-和 3-氧代-1,8-桉树脑。这些代谢物构成了一组结构上密切相关的分子，它们主要在含氧官能团的性质和位置上有所不同。因此，它们提供了将气味特性与分子结构相关联的可能性，即建立从母体物质作为有效气味化合物生物生成的化合物的结构-气味关系。通常，代谢物保留了 1,8-桉树脑的桉树般气味质量，但表现出额外的气味特征，如甜、柑橘、塑料、泥土、发霉和粪便，这使它们可以区分开来。手性分子的单个对映异构体也表现出不同的气味。除 2,3-脱氢-1,8-桉树脑外，所有代谢物的气味阈值均比 1,8-桉树脑显著降低。气味质量和气味阈值的测定是通过非手性和手性 GC 毛细管上的气相色谱/嗅觉测定法 (GC/O) 完成的。结果与常见的结构-气味关系理论相关联。
