Relations structure-odeur de bois de santal: recherche d'un modèle d'interaction fondé sur le concept d'hypermotif santalophore

摘要: Structure-odour relationships for sandalwood odorants were studied a set of 139 compounds (57 active and 82 inactive), essentially alkylcyclohexylalkanols, acyclic, norbornyl, campholenyl decalin derivatives. Active possess only hydroxyl as functional group, but inactive hydroxyl, ketone, epoxide, aldehyde, ester or ether group. In general, these have flexible structure. The first step in the present study consists statistical evaluation empirical rules concerning structure-odour odorants, using discriminant analysis. After testing rules, main structural elements responsible odour are defined from previous rules. Structural which favourable those unfavourable to distinguished. Structural (t-butyl group an equivalent group) found necessary produce fragrance constitute parts santalophore patterns I II. These built Alchemy II program by superposition strong possessing relatively rigid structure. The distance between oxygen atom quaternary carbon (t-butyl) is approximately 7.1 A pattern 6.5 Then cannot be fused unique if one type receptor exists odour. The difference distances observed not very important (0.6 A). molecules probably interact with different same receptor, slightly larger than two patterns. concept superpattern then introduced. The superpattern, envelope patterns, their superposition. It bulky part, more This part constituted hydrogen atoms. Geometric characteristics described elements. Thus, order predict test 17 compounds, 3 types geometric parameters: distances, bond angles dihedral methyl groups part. was that complete discrimination obtained when geometrical parameters used simultaneously. best angle parameters. An interaction model discussed combination some hypotheses on interactions involved. Thus considered dispersion forces bonding interactions. To this hypothesis, α-santalol β-santalol methylated. no odour, confirmed perfumer. We could conclude donor, it interesting note carbonyl such decahydro β-naphtyl formate, acceptors literature reminiscent sandalwood. often compositions character under investigation determine they actually note.