Dependence of biological response on the geometric and electronic characteristics of phenol derivatives with smoke flavour.
On the base of the data of conformational analysis and quantum-chemical calculation (method CNDO/2) of the series of phenol derivatives with smoke flavour it was shown that the structural fragment responsible for the odorant activity consists of the oxygen atom and two hydrogen atoms. The atomic orbitals of these atoms are constituting the highest occupied molecular orbital (HOMO) with the high values of the orbital coefficients of their 2p pi- and 1s-orbitals. The distance between the hydrogen atoms is 1.7-2.5 A, while the average distance (L) from these hydrogen atoms to the oxygen atom is 5.45 +/- 0.85 A. The dependence between the value of psychological response for the presence of the studied compounds within the gaseous phase and the value L was found.
A.V. Bogatsky Physico-Chemical Institute, Academy of Sciences of the Ukraine, Odessa.
Gorbachev MYu
A I
AI
Gren
A V
AV
Manzhos
B A
BA
Lobasyuk
D000818:Animals; D004583:Electrons; D005421:Flavoring Agents / Q000737:chemistry / Q000494:pharmacology*; D006859:Hydrogen / Q000737:chemistry / Q000494:pharmacology; D008297:Male; D008968:Molecular Conformation; D009043:Motor Activity / Q000187:drug effects; D010100:Oxygen / Q000737:chemistry / Q000494:pharmacology; D010636:Phenols / Q000737:chemistry / Q000494:pharmacology*; D051381:Rats; D012903:Smell / Q000502:physiology; D012906:Smoke; D013329:Structure-Activity Relationship
D005421:Flavoring Agents; D010636:Phenols; D012906:Smoke; D006859:Hydrogen; D010100:Oxygen