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

The Lilac Alcohols

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Photo by permission of M. Roudintska - Art & Parfum

 

(2R,2'S,5'S)-Lilac alcohol - green, grassy, fresh

Odor Threshold = 4 ng

= (2R)-2-[(2S,5S)-2,5-dimethyl-5-vinyltetrahydrofuran-2-yl]propanol

Ref: Kreck, M. & A. Mosandl, Synthesis, Structure Elucidation, and Olfactometric Analysis of Lilac Aldehyde and Lilac Alcohol Stereoisomers, Journal of Agricultural and Food Chemistry, J. Agric. Food Chem. 2003, 51, 2722-2726

(2S,2'R,5'R)-Lilac alcohol - sweet

Odor Threshold = 80 ng

= (2S)-2-[(2R,5R)-2,5-dimethyl-5-vinyltetrahydrofuran-2-yl]propanol

Ref: Kreck, M. & A. Mosandl, Synthesis, Structure Elucidation, and Olfactometric Analysis of Lilac Aldehyde and Lilac Alcohol Stereoisomers, Journal of Agricultural and Food Chemistry, J. Agric. Food Chem. 2003, 51, 2722-2726

(2S,2'S,5'S)-Lilac alcohol - flowery

Odor Threshold = 2 ng

= (2S)-2-[(2S,5S)-2,5-dimethyl-5-vinyltetrahydrofuran-2-yl]propanol

Ref: Kreck, M. & A. Mosandl, Synthesis, Structure Elucidation, and Olfactometric Analysis of Lilac Aldehyde and Lilac Alcohol Stereoisomers, Journal of Agricultural and Food Chemistry, J. Agric. Food Chem. 2003, 51, 2722-2726

(2R,2'R,5'R)-Lilac alcohol - odorless at >100 ng by GC sniffing

Odor Threshold = >100 ng

= (2R)-2-[(2R,5R)-2,5-dimethyl-5-vinyltetrahydrofuran-2-yl]propanol

Ref: Kreck, M. & A. Mosandl, Synthesis, Structure Elucidation, and Olfactometric Analysis of Lilac Aldehyde and Lilac Alcohol Stereoisomers, Journal of Agricultural and Food Chemistry, J. Agric. Food Chem. 2003, 51, 2722-2726

(2R,2'R,5'S)-Lilac alcohol - flowery, sweet, body

Odor Threshold = 4 ng

= (2R)-2-[(2R,5S)-2,5-dimethyl-5-vinyltetrahydrofuran-2-yl]propanol

Ref: Kreck, M. & A. Mosandl, Synthesis, Structure Elucidation, and Olfactometric Analysis of Lilac Aldehyde and Lilac Alcohol Stereoisomers, Journal of Agricultural and Food Chemistry, J. Agric. Food Chem. 2003, 51, 2722-2726

(2S,2'S,5'R)-Lilac alcohol - herbaceous, slightly flowery

Odor Threshold = 74 ng

= (2S)-2-[(2S,5R)-2,5-dimethyl-5-vinyltetrahydrofuran-2-yl]propanol

Ref: Kreck, M. & A. Mosandl, Synthesis, Structure Elucidation, and Olfactometric Analysis of Lilac Aldehyde and Lilac Alcohol Stereoisomers, Journal of Agricultural and Food Chemistry, J. Agric. Food Chem. 2003, 51, 2722-2726

(2S,2'R,5'S)-Lilac alcohol - sweet, flowery

Odor Threshold = 2 ng

= (2S)-2-[(2R,5S)-2,5-dimethyl-5-vinyltetrahydrofuran-2-yl]propanol

Ref: Kreck, M. & A. Mosandl, Synthesis, Structure Elucidation, and Olfactometric Analysis of Lilac Aldehyde and Lilac Alcohol Stereoisomers, Journal of Agricultural and Food Chemistry, J. Agric. Food Chem. 2003, 51, 2722-2726

(2R,2'S,5'R)-Lilac alcohol - sweet

Odor Threshold = 22 ng

= (2R)-2-[(2S,5R)-2,5-dimethyl-5-vinyltetrahydrofuran-2-yl]propanol

Ref: Kreck, M. & A. Mosandl, Synthesis, Structure Elucidation, and Olfactometric Analysis of Lilac Aldehyde and Lilac Alcohol Stereoisomers, Journal of Agricultural and Food Chemistry, J. Agric. Food Chem. 2003, 51, 2722-2726

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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