Synthesis of ionones and carvone analogues: olfactory properties and preliminary toxicity assays.
Vilsmeier reagents react with alpha/beta-ionones and carvone to produce aldehydes 7-11 in a one-step procedure. The indene derivative 11, which came from the double iminoalkylation of carvone and ring closure with the elimination of dimethylamine, was practically odourless, while all the others had peculiar odours which were very different from the starting material. The cytotoxicity data of 9 and 10, which are the most promising potential perfume ingredients, are also reported.
Anzaldi
M
M
Dipartimento di Scienze Farmaceutiche, Università degli Studi di Genova, Viale Benedetto XV, 3 - 16132, Genova, Italy.
Sottofattori
E
E
Dusatti
F
F
Ferro
M
M
Pani
M
M
Balbi
A
A
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001547:Benzaldehydes / Q000737:chemistry* / Q000494:pharmacology*; D000081005:Cyclohexane Monoterpenes; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D053138:Cyclohexenes; D004353:Drug Evaluation, Preclinical; D006801:Humans; D020128:Inhibitory Concentration 50; D039821:Monoterpenes; D009812:Odorants; D010476:Perfume / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship; D013729:Terpenes / Q000737:chemistry*; D018675:Toxicity Tests
D000475:Alkenes; D001547:Benzaldehydes; D000081005:Cyclohexane Monoterpenes; D003510:Cyclohexanes; D053138:Cyclohexenes; D039821:Monoterpenes; D010476:Perfume; D013729:Terpenes; C415402:formyl cyclohexadiene; C006923:carvone; C059341:2-chlorobenzaldehyde