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Syntheses, Structures, and Sensory Characteristics of the Perfume Ingredient Majantol and Its Analogs Sila-majantol and Germa-majantol: A Study on C/Si/Ge Bioisosterism§
journal contribution
posted on 2001-12-05, 00:00 authored by Reinhold Tacke, Thomas Schmid, Christian Burschka, Martin Penka, Horst SurburgThe perfume ingredient majantol [2,2-dimethyl-3-(3-methylphenyl)propan-1-ol (1a)] and
its silicon- and germanium-containing analogs sila-majantol [(hydroxymethyl)dimethyl(3-methylbenzyl)silane (1b)] and germa-majantol [(hydroxymethyl)dimethyl(3-methylbenzyl)germane (1c)], respectively, were synthesized from i-PrC(O)Ph (four steps, → 1a),
Me2Si(CH2Cl)Cl (three steps, → 1b), or Cl3GeCH2Cl (four steps, → 1c). The structures of
the C/Si/Ge analogs 1a/1b/1c were determined by crystal structure analyses and computational studies [RI-MP2 calculations (TZVP level)]. The odor of majantol (1a) was found to
be strong fresh-floral, aqueous-aldehydic, and characteristic of lily-of-the-valley flowers,
whereas that of sila-majantol (1b) was considerably less intense than that of 1a. It lacked
the aqueous-aldehydic freshness, but possessed nevertheless the characteristic lily-of-the-valley odor, but it was more terpineol-like. The odor of germa-majantol (1c) was very weak
and not characteristic; the majantol impression could be recognized only as a shade.