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

The Rose oxide ketones

= The 2-acetonyl-4-methyltetrahydropyrans

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Photo by permission of M. Roudintska - Art & Parfum

(-)-(2S,4R)-cis-Rose oxide ketone - Herbal, sweet, typical methyl ketone-like odor

= (-)-(2S,4R)-2-acetonyl-4-methyltetrahydropyran

= (-)-(2S,4R)-1-(tetrahydro-4-methyl-2H-pyran-2-yl)acetone

= (-)-1-((2S,4R)-tetrahydro-4-methyl-2H-pyran-2-yl)propanone

Ref: MatthiasWüst and Armin Mosandl. "Important chiral monoterpenoid ethers in flavours and essential oils–enantioselective analysis and biogenesis." European Food Research and Technology 209, no. 1 (1999): 3-11; Wüst M (1999) Dissertation, Universität Frankfurt am Main

(+)-(2R,4S)-cis-Rose oxide ketone - Herbal, green, sweet, typical methyl ketone-like odor

= (+)-(2R,4S) -2-acetonyl-4-methyltetrahydropyran

= (+)-(2R,4S) -1-(tetrahydro-4-methyl-2H-pyran-2-yl)acetone

= (+)-1-((2R,4S)-tetrahydro-4-methyl-2H-pyran-2-yl)propanone

Ref: MatthiasWüst and Armin Mosandl. "Important chiral monoterpenoid ethers in flavours and essential oils–enantioselective analysis and biogenesis." European Food Research and Technology 209, no. 1 (1999): 3-11; Wüst M (1999) Dissertation, Universität Frankfurt am Main

(2S,4S)-trans-Rose oxide ketone - Odorless up to 1000 ng

= (2S,4S)- 2-acetonyl-4-methyltetrahydropyran

= (2S,4S)- 1-(tetrahydro-4-methyl-2H-pyran-2-yl)acetone

= 1-((2S,4S)-tetrahydro-4-methyl-2H-pyran-2-yl)propanone

Ref: MatthiasWüst and Armin Mosandl. "Important chiral monoterpenoid ethers in flavours and essential oils–enantioselective analysis and biogenesis." European Food Research and Technology 209, no. 1 (1999): 3-11; Wüst M (1999) Dissertation, Universität Frankfurt am Main

 

(2R,4R)-trans-Rose oxide ketone - Odorless up to 1000 ng

= (2R,4R)- 2-acetonyl-4-methyltetrahydropyran

= (2R,4R)- 1-(tetrahydro-4-methyl-2H-pyran-2-yl)acetone

= 1-((2R,4R)-tetrahydro-4-methyl-2H-pyran-2-yl)propanone

Ref: MatthiasWüst and Armin Mosandl. "Important chiral monoterpenoid ethers in flavours and essential oils–enantioselective analysis and biogenesis." European Food Research and Technology 209, no. 1 (1999): 3-11; Wüst M (1999) Dissertation, Universität Frankfurt am Main

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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