Structure-odor relationship study on geraniol, nerol and their synthesized oxygenated derivatives

Journal article


Publication Details

Author(s): Elsharif S, Büttner A
Journal: Journal of Agricultural and Food Chemistry
Publisher: American Chemical Society
Publication year: 2018
ISSN: 0021-8561


Abstract


Despite being isomers having the same citrus-like, floral odor, geraniol, 1, and nerol, 3, show different odor thresholds. To date, no systematic studies are at hand elucidating the structural features required for their specific odor properties. Therefore, starting from these two basic structures and their corresponding esters, namely, geranyl acetate, 2, and neryl acetate, 4, a total of 12 oxygenated compounds were synthesized and characterized regarding retention indices (RI), mass spectrometric (MS), and nuclear magnetic resonance (NMR) data. All compounds were individually tested for their odor qualities and odor thresholds in air (OT). Geraniol, the Z-isomer, with an OT of 14 ng/L, was found to be more potent than its E-isomer, nerol, which has an OT of 60 ng/L. However, 8-oxoneryl acetate was the most potent derivative within this study, exhibiting an OT of 8.8 ng/L, whereas 8-oxonerol was the least potent with an OT of 493 ng/L. Interestingly, the 8-oxo derivatives smell musty and fatty, whereas the 8-hydroxy derivatives show odor impressions similar to those of 1 and 3. 8-Carboxygeraniol was found to be odorless, whereas its E-isomer, 8-carboxynerol, showed fatty, waxy, and greasy impressions. Overall, we observed that oxygenation on C-8 affects mainly the odor quality, whereas the E/Z position of the functional group on C-1 affects the odor potency.


FAU Authors / FAU Editors

Büttner, Andrea Prof. Dr.
Professur für Aromaforschung
Elsharif, Shaimaa
Professur für Aromaforschung


How to cite

APA:
Elsharif, S., & Büttner, A. (2018). Structure-odor relationship study on geraniol, nerol and their synthesized oxygenated derivatives. Journal of Agricultural and Food Chemistry. https://dx.doi.org/10.1021/acs.jafc.6b04534

MLA:
Elsharif, Shaimaa, and Andrea Büttner. "Structure-odor relationship study on geraniol, nerol and their synthesized oxygenated derivatives." Journal of Agricultural and Food Chemistry (2018).

BibTeX: 

Last updated on 2019-21-05 at 11:23