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Comparative Analysis of the Olfactory Properties of Silicon/Germanium/Tin Analogues of the Lily‐of‐the‐Valley Odorants Lilial and Bourgeonal
Author(s) -
Dörrich Steffen,
Gelis Lian,
Wolf Steffen,
Sunderkötter Astrid,
Mahler Christoph,
Guschina Elena,
Tacke Reinhold,
Hatt Hanns,
Kraft Philip
Publication year - 2014
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201402160
Subject(s) - tin , germanium , chemistry , silicon , stereochemistry , odor , receptor , biochemistry , organic chemistry
The silicon/germanium/tin analogues of the lily‐of‐the‐valley odorants lilial ( rac ‐ 1 a ), compounds rac ‐ 1 b , rac ‐ 1 c , and rac ‐ 1 d , and bourgeonal ( 2 a ), compounds 2 b , 2 c , and 2 d , were synthesized and characterized for their olfactory properties, including GC–olfactometry studies. Compounds rac ‐ 1 a – c and 2 a – c possess a typical lily‐of‐the‐valley odor, whereas the stanna‐analogues rac ‐ 1 d and 2 d , despite some floral aspects, clearly no longer belong to the lily‐of‐the‐valley family. In both series of the carbon/silicon/germanium/tin analogues studied, the lily‐of‐the‐valley odor decreases in the order of carbon