Molecular orbital approach to possible discrimination of musk odor intensity

Ishikawa, Y.; Kawakami, Kiyoshi

doi:10.1002/1097-461x(2000)79:2<109::aid-qua6>3.0.co;2-g

“…One enduring puzzle of structure-odor relations is the relationship between musk odor [typically very similar from musk to musk] and molecular structure [very diverse] [32][33][34][35][36]. To this puzzle we tentatively offer a novel solution.…”

Section: Discussionmentioning

confidence: 99%

Correction: Molecular Vibration-Sensing Component in Human Olfaction

Gane¹,

Georganakis²,

Maniati³

et al. 2013

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Whether olfaction recognizes odorants by their shape, their molecular vibrations, or both remains an open and controversial question. A convenient way to address it is to test for odor character differences between deuterated and undeuterated odorant isotopomers, since these have identical ground-state conformations but different vibrational modes. In a previous paper Proc Natl Acad Sci USA 108:9, 3797-802) we showed that fruit flies can recognize the presence of deuterium in odorants by a vibrational mechanism. Here we address the question of whether humans too can distinguish deuterated and undeuterated odorants. A previous report (Keller and Vosshall (2004) Nat Neurosci 7:4, 337-8) indicated that naive subjects are incapable of distinguishing acetophenone and d-8 acetophenone. Here we confirm and extend those results to trained subjects and gas-chromatography [GC]-pure odorants. However, we also show that subjects easily distinguish deuterated and undeuterated musk odorants purified to GC-pure standard. These results are consistent with a vibrational component in human olfaction.

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“…One enduring puzzle of structure-odor relations is the relationship between musk odor [typically very similar from musk to musk] and molecular structure [very diverse] [32][33][34][35][36]. To this puzzle we tentatively offer a novel solution.…”

Section: Discussionmentioning

confidence: 99%

Molecular vibration-sensing component in human olfaction

2013

Br Dent J

0

View full text Add to dashboard Cite

Whether olfaction recognizes odorants by their shape, their molecular vibrations, or both remains an open and controversial question. A convenient way to address it is to test for odor character differences between deuterated and undeuterated odorant isotopomers, since these have identical ground-state conformations but different vibrational modes. In a previous paper Proc Natl Acad Sci USA 108:9, 3797-802) we showed that fruit flies can recognize the presence of deuterium in odorants by a vibrational mechanism. Here we address the question of whether humans too can distinguish deuterated and undeuterated odorants. A previous report (Keller and Vosshall (2004) Nat Neurosci 7:4, 337-8) indicated that naive subjects are incapable of distinguishing acetophenone and d-8 acetophenone. Here we confirm and extend those results to trained subjects and gas-chromatography [GC]-pure odorants. However, we also show that subjects easily distinguish deuterated and undeuterated musk odorants purified to GC-pure standard. These results are consistent with a vibrational component in human olfaction.

show abstract

“…This relatively new approach has been applied by a number of researchers for estimation of odour properties. Ishikawa and Kishi [25] studied 203 musk-related molecules and established a relationship between the electronic parameters of the molecules and their odour intensities by performing a discriminative function analysis and multi-linear regression analysis. Korichiet al [26] developed a QSPR model showing the importance of molecular descriptors to predict the odour quality of 121 molecules of balsamic odour employing artificial neural networks and discriminant analysis after reducing the number of descriptors through a variable selection approach.…”

Section: Introductionmentioning

confidence: 99%

“…This relatively new approach has been applied by a number of researchers for estimation of odour properties. Ishikawa and Kishi studied 203 musk‐related molecules and established a relationship between the electronic parameters of the molecules and their odour intensities by performing a discriminative function analysis and multi‐linear regression analysis. Korichi et al .…”

Section: Introductionmentioning

confidence: 99%

A quantitative structure–property relationship approach to determine the essential molecular functionalities of potent odorants

Pal

¹

,

Mitra

²

,

Roy

³

2013

Flavour & Fragrance J

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For the last 100 years, considerable effort has been oriented towards the investigation of odorous molecules from natural sources and the development of new synthetic odorants. In this search, cheminformatic tools for quantitative structure–property relationships (QSPRs) have been shown to be beneficial for the primary screening of odorant molecules. The present work attempts to identify the distinct chemical features that impart a strong smell to the molecules. Here, genetic/partial least squares (G/PLS) regression has been employed using an easily interpretable descriptor pool for generating a QSPR model to predict odour detection thresholds, using 204 diverse airborne chemicals. The model was rigorously validated using a variety of statistical parameters and different validation metrics which yielded good results. The statistical model developed provides valuable information about the contribution of structural fragments that are essential for lowering the odour threshold of the molecules, which may guide the development of new potent odorants. The interpretation of the descriptors contained in the model provides knowledge about the requirement of nucleophilicity of a molecule in relation to its binding with odorant receptors. Based on the predictive power and interpretability of the model, they might be further utilized for guiding the design and screening of new stronger odorant molecules. Copyright © 2013 John Wiley & Sons, Ltd.

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Molecular orbital approach to possible discrimination of musk odor intensity

Cited by 8 publications

References 18 publications

Correction: Molecular Vibration-Sensing Component in Human Olfaction

Correction: Molecular Vibration-Sensing Component in Human Olfaction

Molecular vibration-sensing component in human olfaction

A quantitative structure–property relationship approach to determine the essential molecular functionalities of potent odorants

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