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

The Dehydrotheaspirones

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Photo by permission of M. Roudintska - Art & Parfum

(6S)-(+)-8,9-dehydrotheaspirone - Fruity-floral aroma (Kataoka, et. al.); floral, woody-ambery, powdery, reminiscent of Cetonal with natural fruity, orris-like facets (Serra, et. al.).

Odor threshold = 100 ppb (Kataoka, et. al.)

Odor threshold (5 panellists) = 9.8 ng/L air (Serra, et. al.).

= (+)-(5S)-2,6,10,10-tetramethyl-1-oxaspiro[4.5]deca-2,6-dien-8-one

Ref: Hitomi Kataoka, Hideki Nakamoto, Taro Kitauro, Masakazu Ishihara, Perfume Quality Improver, Perfume Composition, Cosmetic or Food, Japanese Patent Publication No. 2002069480 (March 8, 2002); Stefano Serra, Assem Barakat and Claudio Fuganti, Chemoenzymatic resolution of cis- and trans-3,6-dihydroxy-a-ionone. Synthesis of the enantiomeric forms of dehydrovomifoliol and 8,9-dehydrotheaspirone, Tetrahedron: Asymmetry 18 (2007) 2573–2580.

(6R)-(-)-8,9-dehydrotheaspirone - Woody aroma (Kataoka, et. al.); woody, dry, cedarwood odor with a green, earthy, tobacco and olibanum inflection and floral-fruity nuances (Serra, et. al.).

Odor threshold = 500 ppb (Kataoka, et. al.)

Odor threshold (5 panellists) = 13.7 ng/L air (Serra, et. al.).

= (-)-(5R)-2,6,10,10-tetramethyl-1-oxaspiro[4.5]deca-2,6-dien-8-one

Ref: Hitomi Kataoka, Hideki Nakamoto, Taro Kitauro, Masakazu Ishihara, Perfume Quality Improver, Perfume Composition, Cosmetic or Food, Japanese Patent Publication No. 2002069479 (March 8, 2002); Stefano Serra, Assem Barakat and Claudio Fuganti, Chemoenzymatic resolution of cis- and trans-3,6-dihydroxy-a-ionone. Synthesis of the enantiomeric forms of dehydrovomifoliol and 8,9-dehydrotheaspirone, Tetrahedron: Asymmetry 18 (2007) 2573–2580.

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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