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

The Theaspiranes

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Photo by permission of M. Roudintska - Art & Parfum

(-)-(2R,5R)-Theaspirane - weak camphoraceous note

Also known as: (-)-(2R,5R)-2,6,10,10-tetramethyl-1-oxaspiro[4.5]dec-6-ene

Ref: Gertraut Schmidt, Gerhard Full, Peter Winterhalter, and Peter Schreier, Synthesis and Enantiodifferentiation of Isomeric Theaspiranes, J. Agric. Food Chem. l992, 40, 1188-1191

(+)-(2S,5S)-Theaspirane - odor of isomer was dominated by a fresh camphoraceous note

Also known as: (+)-(2S,5S)- -2,6,10,10-tetramethyl-1-oxaspiro[4.5]dec-6-ene

Ref: Gertraut Schmidt, Gerhard Full, Peter Winterhalter, and Peter Schreier, Synthesis and Enantiodifferentiation of Isomeric Theaspiranes, J. Agric. Food Chem. l992, 40, 1188-1191

(+)-(2S,5R)-Theaspirane - a camphoraceous - almost naphthalene-like note

Also known as: (+)-(2S,5R)- 2,6,10,10-tetramethyl-1-oxaspiro[4.5]dec-6-ene

Ref: Gertraut Schmidt, Gerhard Full, Peter Winterhalter, and Peter Schreier, Synthesis and Enantiodifferentiation of Isomeric Theaspiranes, J. Agric. Food Chem. l992, 40, 1188-1191

(-)-(2R,5S)-Theaspirane - isomer exhibited a highly attractive, intense fresh-fruity (black currant or cassis) odor

Also known as: (-)-(2R,5S)-2,6,10,10-tetramethyl-1-oxaspiro[4.5]dec-6-ene

Ref: Gertraut Schmidt, Gerhard Full, Peter Winterhalter, and Peter Schreier, Synthesis and Enantiodifferentiation of Isomeric Theaspiranes, J. Agric. Food Chem. l992, 40, 1188-1191

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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