Chirality & Odour Perception
John C. Leffingwell, Ph.D.

The Tropional®s

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Photo by permission of M. Roudintska - Art & Parfum

(+)-(2R)-Tropional® - floral (Lily of the valley and cyclamen), aldehydic, sweet fruity (lemon)

Odor Threshold = 3.43 ng/l in air

= (+)-(2R)-3-(1,3-benzodioxol-5-yl)-2-methylpropanal

Ref: Dieter Enders and Michael Backes, First asymmetric synthesis of both enantiomers of Tropional® and their olfactory evaluation, Tetrahedron: Asymmetry, Volume 15, Issue 11, 7 June 2004, Pages 1813-1817; Michael Backes, Versuche zur ersten Totalsynthese des Aglycons der Cripowelline A und B und erste asymmetrische Synthese von Tropional®, Dissertation - Institut für Organische Chemie der Rheinisch-Westfälischen Technischen Hochschule Aachen (2004)

(-)-(2S)-Tropional® - green floral, marine, ozone-like and salty aspect, fruity sweet, cumin-like undertone

Odor Threshold = 0.64 ng/l in air

The olfafactory evaluation of the two nnantiomers supplied amazing differences both in the intensity and in the characteristic smell notes. The intensity of the (S)-Enantiomer was more than five times as strong as tthr (R)-Enantiomer. Moreover the (R)-Enantiomer was missing the marine and green notes typical for Tropional nearly completely. Altogether it could be said that for the typical smell of the Tropionals® essentially the (S)-Enantiomer is responsible.

= (-)-(2S)-3-(1,3-benzodioxol-5-yl)-2-methylpropanal

Ref: Dieter Enders and Michael Backes, First asymmetric synthesis of both enantiomers of Tropional® and their olfactory evaluation, Tetrahedron: Asymmetry, Volume 15, Issue 11, 7 June 2004, Pages 1813-1817; Michael Backes, Versuche zur ersten Totalsynthese des Aglycons der Cripowelline A und B und erste asymmetrische Synthese von Tropional®, Dissertation - Institut für Organische Chemie der Rheinisch-Westfälischen Technischen Hochschule Aachen (2004)

Cyclic Terpenoid Odorants

Bicyclic Terpenoid Odorants

Acyclic Terpenoid Odorants

Ionones, Irones, Damascones & Structurally Related Odorants

Acyclics (Alcohols, Esters, Acids, Aldehydes)

Lactones

Sesquiterpenoid Related Odorants

Steroid Urine Type Odorants

Sandalwood Type Odorants

Musk Odorants

Miscellaneous

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