Structure-Odor Activity Studies on Derivatives of Aromatic and Oxygenated Monoterpenoids Synthesized by Modifying p-Cymene.,Journal of Natural Products

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Structure-Odor Activity Studies on Derivatives of Aromatic and Oxygenated Monoterpenoids Synthesized by Modifying p-Cymene.
Journal of Natural Products ( IF 3.3 ) Pub Date : 2020-03-20 , DOI: 10.1021/acs.jnatprod.9b00339
Linda Schreiner _{1,

2} , Johannes Bauer ₁ , Eva Ortner ₂ , Andrea Buettner _{1,

2}

Affiliation

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 p-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.

中文翻译：

改性对伞花烃合成芳族和氧合单萜衍生物的结构-气味活性研究。

据报道，胸腺醌具有独特的铅笔状气味，并且是雪松状和雪松木基产品气味（例如铅笔）的冲击性化合物。化合物百里香酚和香芹酚是在植物和食品（如百里香和牛至）中常见的结构相关的增香剂，对它们的整体香气也有重要作用。但是，尚未对这类含氧芳香族单萜类化合物的感官特性进行系统的阐明。为了弥合这一差距并获得对导致铅笔状和木质气味的结构-气味关系的新见解，合成并表征了从百里香酚和香芹酚开始合成的19种对甲基苯丙氨酸的结构相关衍生物。这些化合物的气味阈值范围从2.0 ng / L空气到388.8 ng / L空气，百里香酚和香芹酚的含量最低，百里香氢醌的含量最高。这些化合物的气味大多类似于百里香，牛至和铅笔状，并具有酚类，泥土和药用气味特征，可以与结构图案成功关联。

更新日期：2020-03-20

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