Quantitative structure-retention and structure-odor intensity relationships for a diverse group of odor-active compounds

Abstract

Numerical representations of structure-based features are used to estimate both the retention indexes and sweetnesses of a diverse set of industrially important fragrance compounds. Retention indexes measured on nonpolar as well as polar stationary phases are modeled with accuracies of 3.6% and 5.6% at the mean of the respective retention ranges. Similar success was achieved when the developed equations were applied to predict the retention indexes of external data set compounds. Finally, the implications of using strictly 2-D structural information versus incorporating geometrical information are explored and discussed. The intensity of sweetness attributed to each compound is quantitatively predicted using identical multiple linear regression techniques. Difficulties encountered in this portion of the study warranted a critique of the procedures used to gain access to the odor data. As a consequence, the limited control exerted over several experimental variables is questioned.

Trigeminal Chemosensation

“…Interestingly, all these descriptors are physicochemical parameters and do not involve the precise chemical structures of the compounds. Attempts have also been made to correlate olfactory potency (Anker and Jurs, 1990;Chastrette, 1997;Dravnieks, 1977;Egolf and Jurs, 1993;Hau and Connelll, 1998;Rossiter, 1996;Schnabel, Belitz, and von Ranson, 1988;Shvets and Dimoglo, 1998). For the most part these relationships are difficult to interpret either chemically or mechanistically (Abraham, 1996).…”

Chemical Sensing in Humans and Machines

“…As has been pointed out [13], an important drawback of many structure-activity relationships in olfaction [14][15][16][17][18][19] is the difficult interpretation of the chemical features that are shown to correlate with odor activity.…”

“…To gain a better understanding of how these sensory channels function it is important to know what particular features of chemicals govern their potency as odorants and irritants (including threshold and suprathreshold intensities). Regarding olfaction, a large number of such features have been suggested, including Wiswesser notation formulas [14], structural parameters directly derived from the chemical formula [45] or derived from gas chromatographic measurements [17,19], steric and electronic descriptors [46], molecular vibration [47][48][49], partition coefficients (specifically, water-air and octanol-water) [50] and an electron-topological method [51]. Some of these investigations focused on one or just a few odor qualities (e.g., musk) whereas others studied a broader spectrum.…”

A synthetic library of allylmethoxyphenyl esters: spectral characterization and gas chromatographic behavior

“…Structural parameters that were used for such purposes span from a simple number of specific atoms to more elaborate calculated molecular properties (dipole moments, surfaces, energies, etc.) . Among these, a special position is taken by topological indices (Wiener, Balaban, molecular topological indices, etc.)…”

“…Structural parameters that were used for such purposes span from a simple number of specific atoms to more elaborate calculated molecular properties (dipole moments, surfaces, energies, etc.). [5][6][7] Among these, a special position is taken by topological indices (Wiener, 8 Balaban,9 molecular topological indices, 10 etc.) which usually collectively, but not without limitations, take into account several molecular aspects (size, branching; i.e., connectivity) but are not easily related to a particular physicochemical property.…”