(-)-(2S,4R,6S)-Floropal® - described as typically Vertacetal, with a characteristic rhubarb note. This is the preferred enantiomer. = (-)-(2S,4R,6S)-2,4,6-trimethyl-4-phenyl-1,3-dioxane The odor threshold for the racemate in which all three methyl groups are cis (with the phenyl trans) is 0.85 ppm Commercial Vertacetal® is described as ‘fresh-herbal, typically the impression of grapefruit’ (racemic mixture of 54.38% cis-diastereomers to 44.33% trans-diastereomers) (Pickenhagen, et. al.) Commercial Floropal is said to be ‘herbalfresh, floral-green, similar to chrysanthemum, cyprus, and grapefruit’ (racemic mixture of 63.71% cis-diastereomers to 34.52% trans-diastereomers) (Pickenhagen, et. al.) 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, Volume 86, Issue 3, Date: March 2003, Pages: 592-606; Claus-Hermann Kappey, Bernd Holscher, Wilhelm Pickenhagen, 2,4,6-trimethyl-4-phenyl-1,3-dioxane, United States Patent 6,114,301 (September 5, 2000) Floropal® is a registered trademark of Haarmann & Reimer Vertacetal® is a trademark of Dragoco Gerberding & Co. AG

(-)-(2R,4S,6R)-Floropal® - less interesting than the (-)-(2S,4R,6S)-enantiomer (Brenna et. al.); the racemate is described as strong, herbal-fresh, green, and typical grapefruit (Pickenhagen, et. al.) = (-)-(2R,4S,6R)-2,4,6-trimethyl-4-phenyl-1,3-dioxane 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, Volume 86, Issue 3, Date: March 2003, Pages: 592-606; Claus-Hermann Kappey, Bernd Holscher, Wilhelm Pickenhagen, 2,4,6-trimethyl-4-phenyl-1,3-dioxane, United States Patent 6,114,301 (September 5, 2000) Floropal® is a registered trademark of Haarmann & Reimer

(2R,4R,6R)-Floropal® - less interesting than the (-)-(2S,4R,6S)-enantiomer (Brenna et. al.); the racemate is described as very weak, chemical solvent-like, and to have a detracting influence upon the odour properties of the mixture (Pickenhagen, et. al.). = (2R,4R,6R)-2,4,6-trimethyl-4-phenyl-1,3-dioxane The odor threshold for the racemate in which the two methyl groups and the phenyl are cis is 332 ppm 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, Volume 86, Issue 3, Date: March 2003, Pages: 592-606; Claus-Hermann Kappey, Bernd Holscher, Wilhelm Pickenhagen, 2,4,6-trimethyl-4-phenyl-1,3-dioxane, United States Patent 6,114,301 (September 5, 2000) Floropal® is a registered trademark of Haarmann & Reimer

Ionones, Irones, Damascones & Structurally Related Odorants

Acyclics (Alcohols, Esters, Acids, Aldehydes)

Lactones

Sesquiterpenoid Related Odorants