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

The Okoumals®

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Photo by permission of M. Roudintska - Art & Parfum

(+)-(2S,4S)-Okoumal - weak, ambery with woody facets, somewhat okoumal-like

Odor Threshold = 2.0 ng/L in air (+/-0.72)

= (+)-(2S,4S)-2,4-dimethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-1,3-dioxolane

Ref: Matthias W. Buettner, Christian Burschka, Konstantin Junold, Philip Kraft, Reinhold Tacke, Disila-Okoumal: A Silicon Analogue of the Ambergris Odorant Okoumal, ChemBioChem, Volume 8, Issue 12, Date: August 13, 2007, Pages: 1447-1454

Okoumal is a registered trademark of Givaudan SA

(-)-(2R,4R)-Okoumal - strong, pronounced, typical ambery odor in the okoumal–karanal family, with woody aspects, clearly the strongest okoumal enantiomer on blotter

Odor Threshold = 0.40 ng/L in air (+/-0.14)

= (-)-(2R,4R)-2,4-dimethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-1,3-dioxolane

Ref: Matthias W. Buettner, Christian Burschka, Konstantin Junold, Philip Kraft, Reinhold Tacke, Disila-Okoumal: A Silicon Analogue of the Ambergris Odorant Okoumal, ChemBioChem, Volume 8, Issue 12, Date: August 13, 2007, Pages: 1447-1454

Okoumal is a registered trademark of Givaudan SA

(-)-(2S,4R)-Okoumal - very weak, ambery odor with woody facets, which during dry-down decreases rapidly in intensity

Odor Threshold = 12.5 ng/L in air (+/-0.0)

= (-)-(2S,4R)-2,4-dimethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-1,3-dioxolane

Ref: Matthias W. Buettner, Christian Burschka, Konstantin Junold, Philip Kraft, Reinhold Tacke, Disila-Okoumal: A Silicon Analogue of the Ambergris Odorant Okoumal, ChemBioChem, Volume 8, Issue 12, Date: August 13, 2007, Pages: 1447-1454

Okoumal is a registered trademark of Givaudan SA

(+)-(2R,4S)-Okoumal - ambery, typically in the okoumal–karanal family, with woody aspects, significantly stronger than (+)-(2S,4S)-Okoumal

Odor Threshold = 0.54 ng/L in air (+/-0.52)

= (+)-(2R,4S)-2,4-dimethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-1,3-dioxolane

Ref: Matthias W. Buettner, Christian Burschka, Konstantin Junold, Philip Kraft, Reinhold Tacke, Disila-Okoumal: A Silicon Analogue of the Ambergris Odorant Okoumal, ChemBioChem, Volume 8, Issue 12, Date: August 13, 2007, Pages: 1447-1454

Okoumal is a registered trademark of Givaudan SA

Cyclic Terpenoid Odorants

Bicyclic Terpenoid Odorants

Acyclic Terpenoid Odorants

Ionones, Irones, Damascones & Structurally Related Odorants

Acyclics (Alcohols, Esters, Acids, Aldehydes)

Lactones & Furanones

Sesquiterpenoid Related Odorants

Steroid Urine Type Odorants

Sandalwood Type Odorants

Musk Odorants

Miscellaneous

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