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

The 9,13-epoxy-14,15,16,20-tetranorlabdanes

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Photo by permission of M. Roudintska - Art & Parfum

(-)-(5S,9R,10S)-9b,13-epoxy-14,15,16,20-tetranorlabdane - Strongly odorous -Mostly described as woody ambergris-likein the sense of the tonality of the standard odorant Ambrox; the descriptions musky and balsamic followed.

= (-)-(2R,4a'S,8a'S)-5',5',8a'-trimethyldecahydro-2'H,3H-spiro[furan-2,1'-naphthalene]

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,9S,10R)-9b,13-epoxy-14,15,16,20-tetranorlabdane - Much Weaker odor than its enantiomer and clearly lacking ambergris odor; other descriptors not reported. Imperceptible to 1/3 of panelists

= (+)-(2S,4a'R,8a'R)-5',5',8a'-trimethyldecahydro-2'H,3H-spiro[furan-2,1'-naphthalene]

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,9S,10S)-9a,13-epoxy-14,15,16,20-tetranorlabdane - Clearly lacking ambergris odor; other descrptors not reported.

= (-)-(2S,4a'S,8a'S)-5',5',8a'-trimethyldecahydro-2'H,3H-spiro[furan-2,1'-naphthalene]

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,9R,10R)-9a,13-epoxy-14,15,16,20-tetranorlabdane - Weaker odor than its enantiomer and clearly lacking ambergris odor; other descrptors not reported.

= (+)-(2R,4a'R,8a'R)-5',5',8a'-trimethyldecahydro-2'H,3H-spiro[furan-2,1'-naphthalene]

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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