The Importance of the 5-Alkyl Substituent for the Violet Smell of Ionones: Synthesis of Racemic 5-Demethyl-α-ionone

The Importance of the 5-Alkyl Substituent for the Violet Smell of Ionones: Synthesis of Racemic 5-Demethyl-α-ionone

The synthesis and the odor tonalities of racemic 5-demethyl-α-ionone are described. This synthetic ionone derivative did not show the typical floral-woody violet smell of α-ionone, definitely proving the importance of a suitably sized and spatially oriented alkyl substituent at C(5) for stimulating...

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Veröffentlicht in:Natural product communications 2015-06, Vol.10 (6), p.847-852
Hauptverfasser: Chierici, Serena, Bugoni, Serena, Porta, Alessio, Zanoni, Giuseppe, Vidari, Giovanni
Format: Artikel
Sprache:eng
Schlagworte:
Molecular Structure
Norisoprenoids - chemical synthesis
Norisoprenoids - chemistry
Odorants - analysis
Smell
Stereoisomerism
Viola - chemistry
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Zusammenfassung:The synthesis and the odor tonalities of racemic 5-demethyl-α-ionone are described. This synthetic ionone derivative did not show the typical floral-woody violet smell of α-ionone, definitely proving the importance of a suitably sized and spatially oriented alkyl substituent at C(5) for stimulating olfactory receptors of ionones.
ISSN:1934-578X
1555-9475
DOI:10.1177/1934578X1501000612