Sci. However, no comprehensive studies are at hand to show which structural features are responsible for these prominent effects. Tasev, T., Toléva, P., and Balabanova, V. (1969). ERNESTO VENTÓS, S.A. shall not be held responsible for any damage or injury resulting from contact with the above. 4, 180–192. *Correspondence: Andrea Buettner, Erlangen, Germany, andrea.buettner@fau.de, Front. Aromatherapy: evidence for sedative effects of the essential oil of lavender after inhalation. Zeitschrift Lebensmittel-Untersuchung Forschung 184, 277–282. [Neurophysical effect of Bulgarian essential oils from rose, lavender and geranium]. Facile and efficient syntheses of (±)-(E)-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid and its methyl ester. Food Chem. Acta 563, 353–364. Response to Letter to the Editor regarding “Olfactory influences on mood and autonomic, endocrine, and immune function”. However, we could show that this is compensated by C-8 oxidation yielding 8-oxolinalyl acetate and the 8-carboxylinalyl acetate with low thresholds that are in a comparable range as the threshold of linalool but eliciting different odor attributes. Soc. MS (EI) m/z (%) (rel.int. Tsagkli, A., Hancianu, M., Aprotosoaie, C., Cioanca, O., and Tzakou, O. This joint with geranyl smells like … Prod. ): 210 [M+] (1), 150(18.38), 135(14), 121(19), 107(18.05), 93(26), 82(41), 71(46), 55(29), 43(100). Flavour Fragr. Nevertheless, the main 8-hydroxylinalyl acetate odor attributes were citrus-like … A significant proportion of orally administered linalool follows intermediary metabolic pathways as shown in Scheme 1 (scheme modified from Aprotosoaie et al., 2014). All reactions were monitored by TLC using Kieselgel 60 F254 plates. Odor attributes named by the panelists were citrus-like, sweet, soapy, and lemon-like, whereas no odor was perceived at the sniffing port in case of 8-carboxylinalool. and M. juliana (L.) Benth. The combined ether layers were washed with 50 ml cold water dried and concentrated to give 7 and 8, respectively. The influence of molecular structure on odor qualities and odor detection thresholds of volatile alkylated phenols. In contrast to the latter two compounds, exhibiting intense odor, 8-hydroxylinalool was perceived by most panelists as low in odor intensity even in a concentration of 390 μg/ml at the sniffing port. J. It is worth mentioning that the latter compound was odorless for all panelists in the concentration levels evaluated, that means at a concentration up to about 200 μg/ml. Chemical variability of rosewood (Aniba rosaeodora Ducke) essential oil in french guiana. Z. Naturforsch. In view of linalyl acetate, the citrus-like impression was reported by 60% of the panelists; fatty and soapy were named by 25% while lemon-like and melissa-like attributes were given by only one panelist. Pharm. About 40% of the panel further described the odor as lemon-like and citrus-like while only one panelist gave the attribute balsamic and linalool-like. (2012). 4, 52–57. The identity of all intermediates and synthetic products was determined by MS/EI. FEMS Yeast Res. 31, 2022–2031. Environ. We believe the above information to be correct but we do not present it as all inclusive and as such should be used as a guide. A minor part undergoes partial ring closure to α-terpineol, with the generation of small amounts of geraniol and nerol. Upon oxidation of the 8-oxolinalool to the corresponding 8-carboxylinalool the odor totally disappears. Morio Muscat: demonstration of stereoselective oxygenation and glycosylation. This procedure offers the advantage that compounds that might be present as odor-active impurities in the reference compound are separated from the target odorants during the chromatographic separation step. Acta Hortic. Following GP1, from 1 (4.8 g, 31.1 mmol) and selenium dioxide (3.4 g, 30.4 mmol) in 30 ml dioxane/ethanol 9:1 (v/v), compound 3 was prepared. 3, 53–62. Among them, due to their high volatility, the acyclic monoterpenes are a valuable class of compounds useful for the flavor and fragrance industries (King and Dickinson, 2003). All other compounds investigated within this study exhibited an odor threshold of at least a factor of 2 higher than the threshold of linalool. (2014). doi: 10.1021/jf60186a011, Omori, H., Nakahara, K., and Umano, K. (2011). doi: 10.1016/S0040-4020(01)97963-3. For gaining deeper insights into the metabolic origin and further fate of linalool and its derivatives, studies were carried out to investigate the metabolism of these substances both in plants (Luan et al., 2006) and animals (Chadha and Madyastha, 1984). Geranyl acetate is a monoterpene (a class of terpene that are most often the product of secondary metabolism in plants), and a natural component of over sixty essential ... lavender and geranium flavors to impart a sweet fruity or citrus smell. Luan, F., Mosandl, A., Degenhardt, A., Gubesch, M., and Wüst, M. (2006). Products of linalool reduction (dihydro-, tetrahydrolinalool) were also identified in rodent urine (Aprotosoaie et al., 2014). In consequence, an influence of such components on the results is avoided. (1988). 27, 297–303. Enantiomeric distribution of some linalool containing essential oils and their biological activities. Liu, H.-X., Chen, X.-H., and Huang, C.-S. (2003). Any other structural changes investigated within this study led to either drastic decrease in the potency or even total odor loss. The synthesis and the absolute configurations of lilac alcohols, new naturally occurring odorous ingredients of lilac flower. The odor of linalyl acetate is described as floral, sweet and citric, and additionally as minty and slightly caraway-like (d'Acampora Zellner et al., 2007). Geranyl acetate. Flavonol acylglycosides from flower of Albizia julibrissin and their inhibitory effects on lipid accumulation in 3T3-L1 cells. 19, 425–427. (1973) was used (Scheme 2). ): 170 [M+] (1), 150(16), 135(13), 131(18), 107(17), 95(25), 82(39), 71(44), 55(28), 43(100).
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