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

The 20-Desmethyl-13-desoxyambreinolides

or

8,13-epoxy-14,15,16,20-tetranorlabdanes

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Photo by permission of M. Roudintska - Art & Parfum

(+)-(5S,8R,9R,10S)-20-desmethyl-8a,13-desoxyambreinolide - Moderately strong odor - Mostly described as woody ambergris-like in the sense of the tonality of the standard odorant Ambrox; the descriptions musky and balsamic followed. However, practically 50% of the subjects being extremely odor-sensitive, including all the female participants, indicated tonalities (green, moss and ionone-lke) which cannot or can only with difficulty be associated with ambergris. Less sensitive subjects, however, committed fewer errors.

= (+)-(5S,8R,9R,10S)-8a,13-epoxy-14,15,16,20-tetranorlabdane or (4aR,6aS,10aS,10bR)-7,7,10a-trimethyldodecahydro-1H-benzo[f]chromene

Ref: Günther Ohloff, Christian Vial, Hans Richard Wolf, Kurt Job, Elise Jégou, Judith Polonsky, Edgar Lederer, Stereochemistry-Odor Relationships in Enantiomeric Ambergris Fragrances, Helvetica Chimica Acta, Volume 63, Issue 7, Date: 29 October 1980, Pages: 1932-1946

(-)-(5R,8S,9S,10R)-20-desmethyl-8a,13-desoxyambreinolide - Strong odor; Six out of eight subjects ascribed woody ambergris-like odor qualities to the strong odor of this nor-ether, although its intensity and ambergris tonality differed considerably. The other four highly sensitive participants gave the following description: flowery (female ), cyclohexanone-like (female ) , minty, floor polish (male), and green-peppery (male).

= (-)-(5R,8S,9S,10R)-8a,13-epoxy-14,15,16,20-tetranorlabdane or (4aS,6aR,10aR,10bS)-7,7,10a-trimethyldodecahydro-1H-benzo[f]chromene

Ref: Ref: Günther Ohloff, Christian Vial, Hans Richard Wolf, Kurt Job, Elise Jégou, Judith Polonsky, Edgar Lederer, Stereochemistry-Odor Relationships in Enantiomeric Ambergris Fragrances, Helvetica Chimica Acta, Volume 63, Issue 7, Date: 29 October 1980, Pages: 1932-1946

(+)-(5S,8S,9R,10S)-20-desmethyl-8b,13-desoxyambreinolide - Strongly odorous -Mostly described as woody ambergris-likein the sense of the tonality of the standard odorant Ambrox; the descriptions musky and balsamic followed. Of the 30 member panel the strong odor of this enantiomer (diastereoisomer ) was described as fermented herbs by only one person (female), and as menthol-like by another (male). Neither subject could detect ambergris-like scents in any of this series

= (+)-(5S,8S,9R,10S)-8b,13-epoxy-14,15,16,20-tetranorlabdane or (4aS,6aS,10aS,10bR)-7,7,10a-trimethyldodecahydro-1H-benzo[f]chromene

Ref: Günther Ohloff, Christian Vial, Hans Richard Wolf, Kurt Job, Elise Jégou, Judith Polonsky, Edgar Lederer, Stereochemistry-Odor Relationships in Enantiomeric Ambergris Fragrances, Helvetica Chimica Acta, Volume 63, Issue 7, Date: 29 October 1980, Pages: 1932-1946

(-)-(5R,8R,9S,10R)-20-desmethyl-8b,13-desoxyambreinolide - Strong odor, but not ambergris-like; of the 30 member panel, only one (male) recognized this diastereoisomer to be ambergris-like.

= (-)-(5R,8R,9S,10R)-8b,13-epoxy-14,15,16,20-tetranorlabdane or (4aR,6aR,10aR,10bS)-7,7,10a-trimethyldodecahydro-1H-benzo[f]chromene

Ref: Günther Ohloff, Christian Vial, Hans Richard Wolf, Kurt Job, Elise Jégou, Judith Polonsky, Edgar Lederer, Stereochemistry-Odor Relationships in Enantiomeric Ambergris Fragrances, Helvetica Chimica Acta, Volume 63, Issue 7, Date: 29 October 1980, Pages: 1932-1946

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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