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Structure-odor Relationships of Linalool, Linalyl Acetate and Their Corresponding Oxygenated Derivatives


Structure-odor Relationships of Linalool, Linalyl Acetate and Their Corresponding Oxygenated Derivatives

Shaimaa A Elsharif et al. Front Chem.


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.

Keywords: 8-carboxylinalyl acetate; 8-oxolinalyl acetate; Linalool; gas chromatography-olfactometry; linalyl acetate; odor qualities; odor threshold in air; retention index.


Figure 1
Figure 1
Lavender oil main constituents.
Scheme 1
Scheme 1
Main linalool metabolic pathway in mammals (scheme modified from Aprotosoaie et al., 2014).
Scheme 2
Scheme 2
Synthetic pathways for the synthesis of linalool and linalyl acetate oxygenated derivatives following procedures 1-4.
Figure 2
Figure 2
Influence of oxygenated functional groups on the odor threshold of odorants.

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    1. Andi S. A., Nazeri V., Hadian J., Zamani Z. (2012). A comparison of the essential oil chemical composition of Origanum vulgare L. ssp. vulgare collected in its flowering and seed stages from southern region of Chalus. Maj. Ulum-i Baghbani-i Iran 43, 153Persian–159Persian, 155English.
    1. Aprotosoaie A. C., Hãncianu M., Costache I.-I., Miron A. (2014). Linalool: a review on a key odorant molecule with valuable biological properties. Flavour Fragr. J. 29, 193–219. 10.1002/ffj.3197 - DOI
    1. Buchbauer G., Jirovetz L., Jäger W., Dietrich H., Plank C. (1991). Aromatherapy: evidence for sedative effects of the essential oil of lavender after inhalation. Z. Naturforsch. C 46, 1067–1072. - PubMed
    1. Cal K., Krzyzaniak M. (2006). Stratum corneum absorption and retention of linalool and terpinen-4-ol applied as gel or oily solution in humans. J. Dermatol. Sci. 42, 265–267. 10.1016/j.jdermsci.2006.02.007 - DOI - PubMed
    1. Chadha A., Madyastha K. M. (1984). Metabolism of geraniol and linalool in the rat and effects on liver and lung microsomal enzymes. Xenobiotica 14, 365–374. 10.3109/00498258409151425 - DOI - PubMed

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