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

The 7,11-epoxymegastigma-5(6)-en-9-ols

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Photo by permission of M. Roudintska - Art & Parfum

(+)-(7S,9R)-7,11-epoxymegastigma-5(6)-en-9-ol - Weak, citric, acidic, slightly floral

= (+)-(2R)-1-[(1S)-7,7-dimethyl-1,3,4,5,6,7-hexahydro-2-benzofuran-1-yl]propan-2-ol; Also known as (+)-(R)-1-((S)-1,3,4,5,6,7-hexahydro-4,4-dimethylisobenzofuran-3-yl)propan-2-ol

Ref: Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Synthesis and olfactory evaluation of the enantiomerically enriched forms of 7,11-epoxymegastigma-5(6)-en-9-one and 7,11-epoxymegastigma-5(6)-en-9-ols isomers, identifed in Passiflora edulis, Tetrahedron: Asymmetry, 16 (2005) 1699–1704.

(-)-(7R,9S)-7,11-epoxymegastigma-5(6)-en-9-ol - Weak, floral-fruity, with a woody, cardboard-like nuance and some metallic facets

= (-)-(2S)-1-[(1R)-7,7-dimethyl-1,3,4,5,6,7-hexahydro-2-benzofuran-1-yl]propan-2-ol; Also known as (-)-(S)-1-((R)-1,3,4,5,6,7-hexahydro-4,4-dimethylisobenzofuran-3-yl)propan-2-ol

Ref: Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Synthesis and olfactory evaluation of the enantiomerically enriched forms of 7,11-epoxymegastigma-5(6)-en-9-one and 7,11-epoxymegastigma-5(6)-en-9-ols isomers, identifed in Passiflora edulis, Tetrahedron: Asymmetry, 16 (2005) 1699–1704.

(+)-(7S,9S)-7,11-epoxymegastigma-5(6)-en-9-ol - Weak, floral smell with technical, acidic component, a bit in the direction of rice wine

= (+)-(2S)-1-[(1S)-7,7-dimethyl-1,3,4,5,6,7-hexahydro-2-benzofuran-1-yl]propan-2-ol; Also known as (+)-(S)-1-((S)-1,3,4,5,6,7-hexahydro-4,4-dimethylisobenzofuran-3-yl)propan-2-ol

Ref: Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Synthesis and olfactory evaluation of the enantiomerically enriched forms of 7,11-epoxymegastigma-5(6)-en-9-one and 7,11-epoxymegastigma-5(6)-en-9-ols isomers, identifed in Passiflora edulis, Tetrahedron: Asymmetry, 16 (2005) 1699–1704.

(-)-(7R,9R)-7,11-epoxymegastigma-5(6)-en-9-ol - Weak, citric, acidic, with a sweet floral touch

= (-)-(2R)-1-[(1R)-7,7-dimethyl-1,3,4,5,6,7-hexahydro-2-benzofuran-1-yl]propan-2-ol; Also known as (-)-(R)-1-((R)-1,3,4,5,6,7-hexahydro-4,4-dimethylisobenzofuran-3-yl)propan-2-ol

Ref: Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Synthesis and olfactory evaluation of the enantiomerically enriched forms of 7,11-epoxymegastigma-5(6)-en-9-one and 7,11-epoxymegastigma-5(6)-en-9-ols isomers, identifed in Passiflora edulis, Tetrahedron: Asymmetry, 16 (2005) 1699–1704.

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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