Odour qualities and thresholds of physiological metabolites of 1,8-cineole as an example for structure-activity relationships considering chirality aspects
Kirsch F, Büttner A (2013)
Publication Type: Journal article
Publication year: 2013
Journal
Publisher: Wiley-VCH Verlag / Wiley-Blackwell
Book Volume: 10
Pages Range: 1683-1695
Abstract
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![[BOND]](http://onlinelibrarystatic.wiley.com/undisplayable_characters/00f8ff.gif)
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.
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How to cite
APA:
Kirsch, F., & Büttner, A. (2013). Odour qualities and thresholds of physiological metabolites of 1,8-cineole as an example for structure-activity relationships considering chirality aspects. Chemistry & Biodiversity, 10, 1683-1695. https://dx.doi.org/10.1002/cbdv.201300097
MLA:
Kirsch, Frauke, and Andrea Büttner. "Odour qualities and thresholds of physiological metabolites of 1,8-cineole as an example for structure-activity relationships considering chirality aspects." Chemistry & Biodiversity 10 (2013): 1683-1695.
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