Structure-minty odour relationships: suggestion of an interaction pattern

Chastrette, M.; Rallet, Emanuelle

doi:10.1002/(sici)1099-1026(199801/02)13:1<5::aid-ffj678>3.0.co;2-b

Cited by 27 publications

(21 citation statements)

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“…(+)‐Menthol and (+)‐neomenthol are less minty and more musty 2. The relationship between structure and olfaction was analyzed in terms of receptor interaction 3. Structural requirements include a cyclohexane chair conformation with a larger equatorial alkyl group in the 2‐position and a smaller group in the 5‐position.…”

Section: Band Positions For the Oh Stretching Vibrations Determined mentioning

confidence: 99%

“…Structural requirements include a cyclohexane chair conformation with a larger equatorial alkyl group in the 2‐position and a smaller group in the 5‐position. Furthermore, an equatorial hydrogen‐bond acceptor is needed, preferably in the 1‐position, and to the right of a virtual observer “sitting in the chair” with the large alkyl group near his head 3. In addition to its specific odor, menthol elicits a strong cooling sensation when applied to skin or mucous membranes;1, 4 this sensation is a result of a rather specific stimulation of the thermosensitive TRPM8 cation channel 5.…”

Section: Band Positions For the Oh Stretching Vibrations Determined mentioning

confidence: 99%

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Chirality Recognition in Menthol and Neomenthol: Preference for Homoconfigurational Aggregation

2010

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Section: Band Positions For the Oh Stretching Vibrations Determined mentioning

confidence: 99%

Section: Band Positions For the Oh Stretching Vibrations Determined mentioning

confidence: 99%

Chirality Recognition in Menthol and Neomenthol: Preference for Homoconfigurational Aggregation

2010

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“…They are also one of the main group of secondary metabolites in nature (nearly 23,000 have been described). Also, these compounds have important biomedicinal applications, are consumed by humans in their daily diet [1,[3][4][5][6][7][8] and are atmospheric pollutants [9,10]. From this point of view, a deep knowledge of the molecular structure and possible conformers of this type of compounds would be desirable.…”

Section: Introductionmentioning

confidence: 99%

Chiral terpenes in different phases: R-(−)-camphorquinone studied by IR–Raman–VCD spectroscopies and theoretical calculations

2010

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R-(-)-camphorquinone is a bicyclical terpenoid with many usages and application in different fields. Different experimental and theoretical works reveal that there is only one stable conformer of this chiral chemical species in agreement to the sterical restriction that the bicycle introduces. In the current work, from a complete assignment of the vibrational IR and Raman spectra, we are able to explain the VCD spectrum of the title compound. The recorded spectra of R-(-)-camphorquinone in different phases have been analyzed and compared: the first one in CCl 4 solution, the second one using Nujol and Fluorolube suspensions and the third one using thin films. Finally, to study the coupling between the two C=O stretching normal modes, a NBO analysis is performed. The present work reveals that IR, Raman and VCD, combined with quantum chemical calculations, are helpful complementary techniques to characterize chiral systems, as terpenes, in different phases.

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“…Cost-effective evaluation of ½avour is dif¼cult for a varied and large number of fragrance compounds after synthesis. [3][4][5][6][7][8] With the development of the computer-aided molecule design, there is a motivation to study or design the above-mentioned compounds using computer-aided methods. The major advantage of this approach is that correlation can be obtained based on the descriptors derived solely from the molecular structure of the compounds investigated.…”

Section: Introductionmentioning

confidence: 99%

Classification of the fragrance properties of chemical compounds based on support vector machine and linear discriminant analysis

Luan

Liu

Wen

et al. 2008

Flavour & Fragrance J

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Classi¼cation models of the fragrance properties of chemical compounds were performed using linear and non-linear models. The dataset was divided into three classes on the basis of their fragrances: apple, pineapple and rose. The three-class problem was ¼rst explored by a linear classi¼er approach, using linear discriminant analysis (LDA). A more accurate prediction model, the non-linear machine-learning technique, support vector machine (SVM), was subsequently investigated. Descriptors calculated from the molecular structures alone were used to represent the characteristics of compounds. The model containing four descriptors founded by SVM showed better predictive ability than LDA. The accuracy in the prediction for the three datasets was 96.6%, 80.0% and 100% for SVM, respectively. The results indicate that SVM can be used as a powerful modelling tool for QSAR studies and the selected descriptors can represent the fragrances of these chemical compounds.

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Structure-minty odour relationships: suggestion of an interaction pattern

Cited by 27 publications

References 0 publications

Chirality Recognition in Menthol and Neomenthol: Preference for Homoconfigurational Aggregation

Chirality Recognition in Menthol and Neomenthol: Preference for Homoconfigurational Aggregation

Chiral terpenes in different phases: R-(−)-camphorquinone studied by IR–Raman–VCD spectroscopies and theoretical calculations

Classification of the fragrance properties of chemical compounds based on support vector machine and linear discriminant analysis

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