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

The 2'-isopropyl-1,7,7-trimethylspirobicyclo[2.2.1]heptane-2,4'-[1,3]dioxanes

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Photo by permission of M. Roudintska - Art & Parfum

(-)-(1R,2S,2'S,4R)-2'-isopropyl-1,7,7-trimethylspiro[bicyclo[2.2.1]heptane-2,4'-[1,3]dioxane] - Amber, woody, cedarwood, animal, strong

Odor Threshold = 0.2 ng/liter (in air)

 Ref: Jerzy A. Bajgrowicz and Iris Frank, Camphor-derived amber/woody odorants: 1,7,7-trimethyl-2'-iso-propylspiro[bicyclo[2.2.1]heptane-2,4'-(1,3-dioxanes)] , Tetrahedron: Asymmetry, Volume 12, Issue 14 , 14 August 2001, Pages 2049-2057; Bajgrowicz; Jerzy A., Odorants, United States Patent 5,703,250 (December 30, 1997); Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003);

 

(+)-(1S,2R,2'R,4S)-2'-isopropyl-1,7,7-trimethylspiro[bicyclo[2.2.1]heptane-2,4'-[1,3]dioxane] - Woody, camphoraceous, amber, spicy, weak

1S,2R,4S,2'R)-76a Woody, camphoraceous, amber, spicy, weak

Odor Threshold = 88 ng/liter (in air)

 Ref: Jerzy A. Bajgrowicz and Iris Frank, Camphor-derived amber/woody odorants: 1,7,7-trimethyl-2'-iso-propylspiro[bicyclo[2.2.1]heptane-2,4'-(1,3-dioxanes)] , Tetrahedron: Asymmetry, Volume 12, Issue 14 , 14 August 2001, Pages 2049-2057; Bajgrowicz; Jerzy A., Odorants, United States Patent 5,703,250 (December 30, 1997); Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003);

(+)-(1R,2S,2'R,4R)-2'-isopropyl-1,7,7-trimethylspiro[bicyclo[2.2.1]heptane-2,4'-[1,3]dioxane] - Woody, cedarwood, rosy, spicy, weak

Odor Threshold = 40 ng/liter (in air)

 Ref: Jerzy A. Bajgrowicz and Iris Frank, Camphor-derived amber/woody odorants: 1,7,7-trimethyl-2'-iso-propylspiro[bicyclo[2.2.1]heptane-2,4'-(1,3-dioxanes)] , Tetrahedron: Asymmetry, Volume 12, Issue 14 , 14 August 2001, Pages 2049-2057; Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003);

 

(-)-(1S,2R,2'S,4S)-2'-isopropyl-1,7,7-trimethylspiro[bicyclo[2.2.1]heptane-2,4'-[1,3]dioxane] - Woody, piney, slightly amber, weak

Odor Threshold = 40 ng/liter (in air)

 Ref: Jerzy A. Bajgrowicz and Iris Frank, Camphor-derived amber/woody odorants: 1,7,7-trimethyl-2'-iso-propylspiro[bicyclo[2.2.1]heptane-2,4'-(1,3-dioxanes)] , Tetrahedron: Asymmetry, Volume 12, Issue 14 , 14 August 2001, Pages 2049-2057; Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003);

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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