Premium
Molecular orbital approach to possible discrimination of musk odor intensity
Author(s) -
Ishikawa Youichi,
Kishi Kiyoshi
Publication year - 2000
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/1097-461x(2000)79:2<109::aid-qua6>3.0.co;2-g
Subject(s) - odor , chemistry , molecule , homo/lumo , molecular descriptor , stereochemistry , computational chemistry , quantitative structure–activity relationship , organic chemistry
Despite the recent progress in molecular biology of odor receptors, codes of olfactory molecules, which provide information on odor discrimination, still remain to be elucidated. Musk molecules are known to have a wide variety of chemical structures. To find the reactive sites of musk molecules, we analyzed electronic localization of 203 musk‐related molecules including 139 musks and 64 nonmusks by Computer‐Aided Chemistry Programs (CAChe Programs) with PM3 parameters. The relationship between electronic localization and odor intensities of musk‐related molecules was studied by discriminative function analysis and multiple regression analysis. We found reactive sites with high values of electrophilic frontier densities (EFDs) at appointed positions in musk molecules. EFD is a theoretical index that predicts reactive sites acting as electron donors. Changes in values of EFDs at these positions not only distinguish musks from nonmusks but are also precisely correlated with intensity levels of musk odor. The result indicates that musk molecules have common reactive sites that play a critical role in the interaction with a receptor. Changes in reactivities of these sites correlate with musk odor intensities subjectively judged by perfumers, indicating that human discrimination of musk odor is determined at the stage of interaction between musk molecules and an odor receptor. © 2000 John Wiley & Sons, Inc. Int J Quant Chem 79: 109–119, 2000