Elsharif Shaimaa A, Banerjee Ashutosh, Buettner Andrea
Department of Chemistry and Pharmacy, Food Chemistry, Emil Fischer Center, Friedrich-Alexander-Universität Erlangen-Nürnberg Erlangen, Germany.
Department of Chemistry and Pharmacy, Pharmaceutical Chemistry, Emil Fischer Center, Friedrich-Alexander-Universität Erlangen-Nürnberg Erlangen, Germany.
Front Chem. 2015 Oct 6;3:57. doi: 10.3389/fchem.2015.00057. eCollection 2015.
Linalool 1 is an odorant that is commonly perceived as having a pleasant odor, but is also known to elicit physiological effects such as inducing calmness and enhancing sleep. However, no comprehensive studies are at hand to show which structural features are responsible for these prominent effects. Therefore, a total of six oxygenated derivatives were synthesized from both 1 and linalyl acetate 2, and were tested for their odor qualities and relative odor thresholds (OTs) in air. Linalool was found to be the most potent odorant among the investigated compounds, with an average OT of 3.2 ng/L, while the 8-hydroxylinalool derivative was the least odorous compound with an OT of 160 ng/L; 8-carboxylinalool was found to be odorless. The odorant 8-oxolinalyl acetate, which has very similar odor properties to linalool, was the most potent odorant besides linalool, exhibiting an OT of 5.9 ng/L. By comparison, 8-carboxylinalyl acetate had a similar OT (6.1 ng/L) as its corresponding 8-oxo derivative but exhibited divergent odor properties (fatty, greasy, musty). Overall, oxygenation on carbon 8 had a substantial effect on the aroma profiles of structural derivatives of linalool and linalyl acetate.
芳樟醇1是一种通常被认为具有宜人气味的气味剂，但也已知会引发诸如诱导平静和改善睡眠等生理效应。然而，目前尚无全面的研究表明哪些结构特征导致了这些显著效果。因此，从1和乙酸芳樟酯2总共合成了六种氧化衍生物，并对它们在空气中的气味质量和相对气味阈值（OTs）进行了测试。在研究的化合物中，芳樟醇被发现是最有效的气味剂，平均OT为3.2 ng/L，而8-羟基芳樟醇衍生物是气味最小的化合物，OT为160 ng/L；8-羧基芳樟醇被发现无气味。乙酸8-氧代芳樟酯的气味特性与芳樟醇非常相似，是除芳樟醇外最有效的气味剂，OT为5.9 ng/L。相比之下，乙酸8-羧基芳樟酯的OT（6.1 ng/L）与其相应的8-氧代衍生物相似，但表现出不同的气味特性（脂肪味、油腻味、霉味）。总体而言，8位碳上的氧化对芳樟醇和乙酸芳樟酯结构衍生物的香气特征有重大影响。
