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

The 2,4-Dimethyl-2-(1,1,3,3-tetramethyl-2-oxa-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-2-oxa-1,3-disilaindan-5-yl)-1,3-dioxolane - a woody–ambery odor in the okoumal family with some additional facets reminiscent of karanal; linear in the drydown, slightly sweet–musky in the endnote

Odor threshold = 1.8 ngL-1 air (+/-0.88 s.d.)

= 1,3-dihydro-1,1,3,3-tetramethyl-5-((2S,4S)-2,4-dimethyl-1,3-dioxolan-2-yl)benzo[c][1,2,5]oxadisilole

= 5-[(2S,4S)-2,4-dimethyl-1,3-dioxolan-2-yl]-1,1,3,3-tetramethyl-1,3-dihydro-benzo[c][1,2,5]oxadisilole

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-2-oxa-1,3-disilaindan-5-yl)-1,3-dioxolane - typical and linear woody–ambery odor, reminiscent of okoumal, but very weak

Odor threshold = 22 ngL-1 air (+/-15 s.d)

= 1,3-dihydro-1,1,3,3-tetramethyl-5-((2R,4R)-2,4-dimethyl-1,3-dioxolan-2-yl)benzo[c][1,2,5]oxadisilole

= 5-[(2R,4R)-2,4-dimethyl-1,3-dioxolan-2-yl]-1,1,3,3-tetramethyl-1,3-dihydro-benzo[c][1,2,5]oxadisilole

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-2-oxa-1,3-disilaindan-5-yl)-1,3-dioxolane - very weak woody–ambery odor with some resemblance to okoumal

Odor threshold = 17 ngL-1 air (+/-20 s.d.)

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

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

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-2-oxa-1,3-disilaindan-5-yl)-1,3-dioxolane - intense woody–ambery okoumal odor with a somewhat pungent, slightly sulfury character

Odor threshold = 2.9 ngL-1 air (+/-1.7 s.d.)

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

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

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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