Structure-Odor Activity Studies on Derivatives of Aromatic and Oxygenated Monoterpenoids Synthesized by Modifying p-Cymene

Schreiner L, Bauer J, Ortner E, Büttner A (2020)

Publication Type: Journal article

Publication year: 2020

Journal

Journal of Natural Products American Chemical Society

DOI: 10.1021/acs.jnatprod.9b00339

Abstract

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.

Authors with CRIS profile

Linda Schreiner Lehrstuhl für Aroma- und Geruchsforschung Johannes Bauer Lehrstuhl für Anorganische und Allgemeine Chemie Andrea Büttner Lehrstuhl für Aroma- und Geruchsforschung

Involved external institutions

Fraunhofer-Institut für Verfahrenstechnik und Verpackung (IVV) DE Germany (DE)

How to cite

APA:

Schreiner, L., Bauer, J., Ortner, E., & Büttner, A. (2020). Structure-Odor Activity Studies on Derivatives of Aromatic and Oxygenated Monoterpenoids Synthesized by Modifying p-Cymene. Journal of Natural Products. https://doi.org/10.1021/acs.jnatprod.9b00339

MLA:

Schreiner, Linda, et al. "Structure-Odor Activity Studies on Derivatives of Aromatic and Oxygenated Monoterpenoids Synthesized by Modifying p-Cymene." Journal of Natural Products (2020).

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