Investigation of odors in the fragrance industry

Schilling, Boris; Kaiser, Roman; Natsch, Andreas; Gautschi, Markus

doi:10.1007/s00049-009-0035-5

Cited by 73 publications

(67 citation statements)

References 65 publications

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“…Perireceptor events and/or psychophysical processes are known to be important in olfaction (2,57) and may result in different olfactory percept of isotopomers. For example, it has been proposed that the nasopharyngeal mucus "behaves like a polar chromatographic column" (58), with differential diffusion rates, air/mucus partition coefficients (59), and solubility toward dissolved odorants (60), potentially leading to separation of isotopomers.…”

Section: Response Of a Human Musk Or To Deuterated And Nondeuteratedmentioning

confidence: 99%

Implausibility of the vibrational theory of olfaction

Block

Jang

Matsunami

et al. 2015

Proc. Natl. Acad. Sci. U.S.A.

115

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The vibrational theory of olfaction assumes that electron transfer occurs across odorants at the active sites of odorant receptors (ORs), serving as a sensitive measure of odorant vibrational frequencies, ultimately leading to olfactory perception. A previous study reported that human subjects differentiated hydrogen/ deuterium isotopomers (isomers with isotopic atoms) of the musk compound cyclopentadecanone as evidence supporting the theory. Here, we find no evidence for such differentiation at the molecular level. In fact, we find that the human musk-recognizing receptor, OR5AN1, identified using a heterologous OR expression system and robustly responding to cyclopentadecanone and muscone, fails to distinguish isotopomers of these compounds in vitro. Furthermore, the mouse (methylthio)methanethiol-recognizing receptor, MOR244-3, as well as other selected human and mouse ORs, responded similarly to normal, deuterated, and 13 C isotopomers of their respective ligands, paralleling our results with the musk receptor OR5AN1. These findings suggest that the proposed vibration theory does not apply to the human musk receptor OR5AN1, mouse thiol receptor MOR244-3, or other ORs examined. Also, contrary to the vibration theory predictions, muscone-d 30 lacks the 1,380-to 1,550-cm −1 IR bands claimed to be essential for musk odor. Furthermore, our theoretical analysis shows that the proposed electron transfer mechanism of the vibrational frequencies of odorants could be easily suppressed by quantum effects of nonodorant molecular vibrational modes. These and other concerns about electron transfer at ORs, together with our extensive experimental data, argue against the plausibility of the vibration theory.olfaction | isotopomers | cyclopentadecanone | muscone | electron transfer I n 1870, the British physician William Ogle wrote: "As in the eye and the ear the sensory impression is known to result not from the contact of material particles given off by the object seen or heard, but from waves or undulations of the ether or the air, one cannot but suspect that the same may be true in the remaining sense, and that the undulatory theory of smell. . . [may be] the true one" (1, 2). Of the 29 different "theories of odour" listed in the 1967 edition of The Chemical Senses (3), nine associate odor with vibrations, particularly those theories championed by Dyson (4, 5) and Wright (6-8). However, the premise that olfaction involves detection of vibrational frequencies of odorants remains highly speculative because neither the structures of the odorant receptors (ORs) nor the binding sites or the activation mechanisms triggered upon odorant binding to ORs have been established. In 1996-1997, Turin (9-12) elaborated on the undulatory theory of smell, as considered in more detail below, and suggested that a mechanism analogous to inelastic electron tunneling spectroscopy (13) may be involved, where tunneling electrons in the receptor probe the vibrational frequencies of odorants. In 2013, Gane et al. (14) In judging the plausibility...

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Section: Response Of a Human Musk Or To Deuterated And Nondeuteratedmentioning

confidence: 99%

Implausibility of the vibrational theory of olfaction

Block

Jang

Matsunami

et al. 2015

Proc. Natl. Acad. Sci. U.S.A.

115

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“…This mucus contains, amongst others, enzymes such as members of the cytochrome P450 system which may convert odorants into other derivatives before reaching the receptor sites. Consequently, smell character as well as intensity may be impacted by such biotransformation processes (Chougnet, Woggon, Locher, & Schilling, 2009;Nagashima & Touhara, 2010;Schilling, Kaiser, Natsch, & Gautschi, 2010;Zhang et al, 2005). However, in the case of the guaiacol derivatives, such potential bioconversion has not been reported until today.…”

Section: Individual Odor Thresholdsmentioning

confidence: 99%

Influence of the chemical structure on the odor qualities and odor thresholds of guaiacol-derived odorants, Part 1: Alkylated, alkenylated and methoxylated derivatives

et al. 2017

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“…Although petals are the main source of flower fragrance (Dobson et al 1990;Goodwin et al 2003;Pichersky et al 1994), the contribution of other floral organs, such as the calyx, stamens (pollen), and nectaries, cannot be ignored (Dobson et al 1990(Dobson et al , 1999Bergström et al 1995;Dudareva et al 2004). While terpenoids are the main component of floral scent (Schilling et al 2010), a variety of other compounds also contribute to fragrance as well. For example, 1,4 dimethoxybenzene is the main component of Salix caprea flowers .…”

Section: Introductionmentioning

confidence: 99%

Corolla structure and fragrance components in Styrax tonkinensis

2015

Trees

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Key message The structure of petals and volatile compounds from fresh Styrax tonkinensis cut flowers were investigated by using micro-techniques and a headspace solid-phase micro-extraction technique coupled with GC-MS. Abstract Styrax tonkinensis is a fast-growing woody plant that is used for timber and as a medicinal plant. In the present study, the structures of the flower petals of S. tonkinensis were investigated and volatile compounds emitted from the petals were identified. Light microscopy, scanning and transmission electron microscopy were used to describe petal structure. The volatile constituents were analyzed using a headspace GC-MS technique. Results indicated that glandular hairs and 8-9 layers of parenchyma cells in the cream-white petals play a key role in emitting the fragrance. An analysis of the volatile components emitted by the cut flowers of S. tonkinensis at two stages of flower development (prior to and at anthesis) indicated that monoterpenes, such as 1,3,6-octatriene, 3,7-dimethyl-(Z), and a-pinene, were the most abundant volatile components in all samples.

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Investigation of odors in the fragrance industry

Cited by 73 publications

References 65 publications

Implausibility of the vibrational theory of olfaction

Implausibility of the vibrational theory of olfaction

Influence of the chemical structure on the odor qualities and odor thresholds of guaiacol-derived odorants, Part 1: Alkylated, alkenylated and methoxylated derivatives

Corolla structure and fragrance components in Styrax tonkinensis

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