Schreiner Linda, Bauer Johannes, Ortner Eva, Buettner Andrea
Aroma and Smell Research, Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU), Henkestraße 9, 91054 Erlangen, Germany.
Department of Sensory Analytics, Fraunhofer Institute for Process Engineering and Packaging (IVV), Giggenhauser Straße 35, 85354 Freising, Germany.
J Nat Prod. 2020 Apr 24;83(4):834-842. doi: 10.1021/acs.jnatprod.9b00339. Epub 2020 Mar 20.
Thymoquinone was recently reported as having a unique pencil-like odor and being the impact compound for the cedar-like and cedar wood-based product smell such as pencils. The compounds thymol and carvacrol are structurally related odorants commonly found in plants and foods such as thyme and oregano, also having a significant contribution to their overall aroma. However, a systematic elucidation of the sensory properties in this class of oxygenated, aromatic monoterpenoids has not been carried out. To close this gap and gain new insights into structure-odor relationships leading to pencil-like and woody odors, 19 structurally related derivatives of -cymene starting from thymol and carvacrol were synthesized and characterized. The compounds had odor thresholds ranging from 2.0 ng/L air to 388.8 ng/L air, being lowest for thymol and carvacrol and highest for thymohydroquinone. The compounds smelled mostly thyme-like, oregano-like, and pencil-like with phenolic, earthy, and medicinal variations in their odor character, which could be successfully linked to structural motifs.
最近有报道称，百里醌具有独特的铅笔般气味，是铅笔等雪松类及雪松木质产品气味的影响化合物。百里香酚和香芹酚是结构相关的气味剂，常见于植物和食物中，如百里香和牛至，它们对这些物质的整体香气也有重要贡献。然而，尚未对这类含氧芳香单萜类化合物的感官特性进行系统阐释。为填补这一空白并深入了解导致铅笔般气味和木质气味的结构 - 气味关系，合成并表征了19种从百里香酚和香芹酚出发的结构相关的对异丙基甲苯衍生物。这些化合物的气味阈值在2.0 ng/L空气至388.8 ng/L空气之间，百里香酚和香芹酚的阈值最低，百里氢醌的阈值最高。这些化合物大多闻起来像百里香、牛至和铅笔，其气味特征带有酚类、泥土味和药味变化，这些变化可成功地与结构基序联系起来。
