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

Magnolan enantiomers

The 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxines

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Photo by permission of M. Roudintska - Art & Parfum

(-)-(1S,3S,4aR,9aS)-Magnolan "B" - was highly appreciated and found rosy, floral (geranium, magnolia), citronellyl acetate, citric-fruity, with a slight green nuance. (-)-(1S,3S,4aR,9aS)-Magnolan is the most interesting enantiomer of the diastereoisomers. It should be noted that relative configuration for this enantiomer is the same as observed for the preferred enantiomer of Floropal

= (-)-(2S,4S,4aS,9bR)-2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine

Ref: Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003); A. Abate, E. Brenna, F. Fronza, C. Fuganti, S. Ronzani, S. Serra, Helv. Chim. Acta, in press (as of Jan. 2003)

Magnolan is a trademark of Symrise

(+)-(1R,3R,4aS,9aR)-Magnolan "B" - was described as weak, acidic, floral, rosy, sweet, warm

= (+)-(2R,4R,4aR,9bS)-2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine

Ref: Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003); A. Abate, E. Brenna, F. Fronza, C. Fuganti, S. Ronzani, S. Serra, Helv. Chim. Acta, in press (as of Jan. 2003)

Magnolan is a trademark of Magnolan is a trademark of Symrise

(+)-(1R,3R,4aR,9aS)-Magnolan "A" - while the odor of the individual enantiomers was not given, the odor of the racemic Magnolan "A" was described as being richer than commercial Magnolan, less plastic and more floral, but the racemic Magnolan "B" was described to be more powerful, much fresher and with an additional pleasant marine tonality, also more substantive on blotter

= (+)-(2R,4R,4aS,9bR)-2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine

Commercial Magnolan is described by Haarmann & Reimer as - Floral-green, reminiscent of magnolia, peony, geranium, grapefruit and lychee, with an indolic nuance.

Ref: Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003); A. Abate, E. Brenna, F. Fronza, C. Fuganti, S. Ronzani, S. Serra, Helv. Chim. Acta, in press (as of Jan. 2003)

Magnolan is a trademark of Symrise

(-)-(1S,3S,4aS,9aR)-Magnolan "A" - while the odor of the individual enantiomers was not given, the odor of the racemic Magnolan "A" was described as being richer than commercial Magnolan, less plastic and more floral, but the racemic Magnolan "B" was described to be more powerful, much fresher and with an additional pleasant marine tonality, also more substantive on blotter

= (-)-(2S,4S,4aR,9bS)-2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine

Commercial Magnolan is described by Haarmann & Reimer as - Floral-green, reminiscent of magnolia, peony, geranium, grapefruit and lychee, with an indolic nuance.

Ref: Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003); A. Abate, E. Brenna, F. Fronza, C. Fuganti, S. Ronzani, S. Serra, Helv. Chim. Acta, in press (as of Jan. 2003)

Magnolan is a trademark of Symrise

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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