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

The 2,4-Dimethyl-2-(1,1,3,3-tetramethyl-1,3-disilaindan-5-yl)-1,3-dioxolanes

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Photo by permission of M. Roudintska - Art & Parfum

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(2S,4S)-2,4-Dimethyl-2-(1,1,3,3-tetramethyl-1,3-disilaindan-5-yl)-1,3-dioxolane - agrestic, borneol-like odor of woody–earthy character with some aspects of wet moss (not ambery at all)

Odor threshold = 10 ngL-1 air (+/- 8.2 s.d.)

= 2,3-dihydro-1,1,3,3-tetramethyl-5-((2S,4S)-2,4-dimethyl-1,3-dioxolan-2-yl)-1H-benzo[d][1,3]disilole

Ref: Jennifer B. Natscher, Nadine Laskowski, Philip Kraft, and Reinhold Tacke, Lower Homologues of Okoumal and Disila-Okoumal: Synthesis and Olfactory Characterization of Novel Ambergris Odorants, ChemBioChem, 2010, 11, 315 – 319

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(2R,4R)-2,4-Dimethyl-2-(1,1,3,3-tetramethyl-1,3-disilaindan-5-yl)-1,3-dioxolane - powerful woody–ambery odor in the direction of okoumal with weak musk facets and a slightly sweat-like undertone

Odor threshold = 0.5 ngL-1 air (+/- 0.0 s.d.)

= 2,3-dihydro-1,1,3,3-tetramethyl-5-((2R,4R)-2,4-dimethyl-1,3-dioxolan-2-yl)-1H-benzo[d][1,3]disilole

Ref: Jennifer B. Natscher, Nadine Laskowski, Philip Kraft, and Reinhold Tacke, Lower Homologues of Okoumal and Disila-Okoumal: Synthesis and Olfactory Characterization of Novel Ambergris Odorants, ChemBioChem, 2010, 11, 315 – 319

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(2S,4R)-2,4-Dimethyl-2-(1,1,3,3-tetramethyl-1,3-disilaindan-5-yl)-1,3-dioxolane - similar woody–ambery note in the direction of okoumal, but overall clearly weaker than the (2R,4R)-enantiomer

Odor threshold = 3.1 ngL-1 air (+/- 1.4 s.d.)

= 2,3-dihydro-1,1,3,3-tetramethyl-5-((2S,4R)-2,4-dimethyl-1,3-dioxolan-2-yl)-1H-benzo[d][1,3]disilole

Ref: Jennifer B. Natscher, Nadine Laskowski, Philip Kraft, and Reinhold Tacke, Lower Homologues of Okoumal and Disila-Okoumal: Synthesis and Olfactory Characterization of Novel Ambergris Odorants, ChemBioChem, 2010, 11, 315 – 319

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(2R,4S)-2,4-Dimethyl-2-(1,1,3,3-tetramethyl-1,3-disilaindan-5-yl)-1,3-dioxolane - dry woody–ambery odor reminiscent of okoumal with green, resinous facet

Odor threshold = 1.0 ngL-1 air (+/- 2.0 s.d.)

= 2,3-dihydro-1,1,3,3-tetramethyl-5-((2R,4S)-2,4-dimethyl-1,3-dioxolan-2-yl)-1H-benzo[d][1,3]disilole

Ref: Jennifer B. Natscher, Nadine Laskowski, Philip Kraft, and Reinhold Tacke, Lower Homologues of Okoumal and Disila-Okoumal: Synthesis and Olfactory Characterization of Novel Ambergris Odorants, ChemBioChem, 2010, 11, 315 – 319

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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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