The Fenchone oximes

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

The Fenchone oximes

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Photo by permission of M. Roudintska - Art & Parfum

(+)-(1S,4R)-Fenchone oxime - roasted onion fragrance

= (+)-(1S,4R)-1,3,3-Trimethylbicyclo[2.2.1]heptane-2-one oxime

 Ref: Daniel Jan Strub, Lucyna Balcerzak, Maria Niewiadomska, Józef Kula, Magdalena Sikora, Julia Gibka, and Stanislaw Lochynski. "Stereochemistry of terpene derivatives. Part 8: synthesis of novel terpenoids from (1S,4R)- and (1R,4S)-fenchone and their comparative odour characteristics." Tetrahedron: Asymmetry 25, no. 13 (2014): 1038-1045.

(-)-(1R,4S)-Fenchone oxime - weak, turnip fragrance

= (-)-(1R,4S)-1,3,3-Trimethylbicyclo[2.2.1]heptane-2-one oxime

 Ref: Daniel Jan Strub, Lucyna Balcerzak, Maria Niewiadomska, Józef Kula, Magdalena Sikora, Julia Gibka, and Stanislaw Lochynski. "Stereochemistry of terpene derivatives. Part 8: synthesis of novel terpenoids from (1S,4R)- and (1R,4S)-fenchone and their comparative odour characteristics." Tetrahedron: Asymmetry 25, no. 13 (2014): 1038-1045.

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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