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Significance of the Geminal Dimethyl Group in the Odor Principle of Ambrox ®
Author(s) -
Ohloff Günther,
Giersch Wolfgang,
Pickenhagen Wilhelm,
Furrer Anton,
Frei Beatrice
Publication year - 1985
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19850680726
Subject(s) - chemistry , geminal , odor , tricyclic , group (periodic table) , carbonyl group , computational chemistry , medicinal chemistry , stereochemistry , organic chemistry
The diastereoisomeric 18‐nor‐ and 19‐norambrox ((6α)‐ and (6β)‐dodecahydro‐3a,6,9a‐trimethylnaphtho[2,1‐ b ]furans resp.) as well as the corresponding 18,19‐dinor‐derivatives (dodecahydro‐3a,9a‐dimethylnaphtho[2,1‐ b ]furans) have been synthesized and subjected to sensory evaluation. Threshold data and odor determination give an enlarged insight into the structure‐activity relationship (SAR) in ambrox‐type ambergris fragrances. As a general conclusion, the accumulation of axial CH 3 groups in the tricyclic ethers 1 – 12 leads to the strongest receptor affinity.