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

The Sedanenolides

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Photo by permission of M. Roudintska - Art & Parfum

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(-)-(S)-Sedanenolide - Celery stem odor, strong, fresh, with aspects reminiscent of celery fibers.

Odor threshold = 0.14 ppm

= (-)-(S)-3-butyl-4,5-dihydroisobenzofuran-1(3H)-one or (-)-(S)-3-butyl-4,5-dihydro-2-benzofuran-1(3H)-one

Ref: D. Oguro & H. Watanabe, Asymmetric Synthesis and Sensory Evaluation of Sedanenolide, Biosci. Biotechnol. Biochem., 75 (8), 1502-1505 (2011)

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(+)-(R)-Sedanenolide - Celery stem odor, bitter, Less intense in fresh celery odor than (S)-(-)-enantiomer

Odor threshold = 0.60 ppm

= (+)-(R)-3-butyl-4,5-dihydroisobenzofuran-1(3H)-one or (+)-(R)-3-butyl-4,5-dihydro-2-benzofuran-1(3H)-one

Ref: D. Oguro & H. Watanabe, Asymmetric Synthesis and Sensory Evaluation of Sedanenolide, Biosci. Biotechnol. Biochem., 75 (8), 1502-1505 (2011)

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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