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

Nat Prod Commun. 2015 Jun;10(6):847-52.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Molecular Structure
  • Norisoprenoids / chemical synthesis*
  • Norisoprenoids / chemistry
  • Odorants / analysis
  • Smell
  • Stereoisomerism
  • Viola / chemistry*

Substances

  • Norisoprenoids
  • alpha-ionone