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

The 3,4-Dihydro-3-oxoedulans

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Photo by permission of M. Roudintska - Art & Parfum

(2S,8aR)-3,4-Dihydro-3-oxoedulan - In the mixture of 2S,8aS (see below) and 2S,8aR isomers (2S,8aS : 2S,8aR ratio of 15:85), a camphoraceous note dominated; Using GC sniffing, the 3,4-dihydro-3-oxoedulans exhibited only weak odor intensities.

Also known as: (2S,8aR)-2,5,5,8a-tetramethyl-2,3,5,6,8,8a-hexahydro-7H-chromen-7-one

Ref: Gertraut Schmidt, Wolfgang Neugebauer, Peter Winterhalter, and Peter Schreier, Synthesis and Enantiodifferentiation of Isomeric 2,3,5,6,8,8a-Hexahydro-2,5,5,8a- tetramethyl-7H- 1-benzopyran-7-ones (3,4-Dihydro-3-oxoedulans), J. Agric. Food Chem. 1995, 43, 1898-1902

(2R,8aS)-3,4-Dihydro-3-oxoedulan - In the mixture of of 2R,8aR (see below) and 2R,8aS isomers (2R,8aR : 2R,8aS ratio of 15:85), a weak tobacco note was detectable; Using GC sniffing, the 3,4-dihydro-3-oxoedulans exhibited only weak odor intensities.

Also known as: (2R,8aS)-2,5,5,8a-tetramethyl-2,3,5,6,8,8a-hexahydro-7H-chromen-7-one

Ref: Gertraut Schmidt, Wolfgang Neugebauer, Peter Winterhalter, and Peter Schreier, Synthesis and Enantiodifferentiation of Isomeric 2,3,5,6,8,8a-Hexahydro-2,5,5,8a- tetramethyl-7H- 1-benzopyran-7-ones (3,4-Dihydro-3-oxoedulans), J. Agric. Food Chem. 1995, 43, 1898-1902

(2S,8aS)-3,4-Dihydro-3-oxoedulan - In the mixture of 2S,8aS and 2S,8aR isomers (2S,8aS : 2S,8aR ratio of 15:85), a camphoraceous note dominated; Using GC sniffing, the 3,4-dihydro-3-oxoedulans exhibited only weak odor intensities.

Also known as: (2S,8aS)- -2,5,5,8a-tetramethyl-2,3,5,6,8,8a-hexahydro-7H-chromen-7-one

Ref: Gertraut Schmidt, Wolfgang Neugebauer, Peter Winterhalter, and Peter Schreier, Synthesis and Enantiodifferentiation of Isomeric 2,3,5,6,8,8a-Hexahydro-2,5,5,8a- tetramethyl-7H- 1-benzopyran-7-ones (3,4-Dihydro-3-oxoedulans), J. Agric. Food Chem. 1995, 43, 1898-1902

(2R,8aR)-3,4-Dihydro-3-oxoedulan - In the mixture of of 2R,8aR and 2R,8aS isomers (2R,8aR : 2R,8aS ratio of 15:85), a weak tobacco note was detectable; Using GC sniffing, the 3,4-dihydro-3-oxoedulans exhibited only weak odor intensities.

Also known as: (2R,8aR)-2,5,5,8a-tetramethyl-2,3,5,6,8,8a-hexahydro-7H-chromen-7-one

Ref: Gertraut Schmidt, Wolfgang Neugebauer, Peter Winterhalter, and Peter Schreier, Synthesis and Enantiodifferentiation of Isomeric 2,3,5,6,8,8a-Hexahydro-2,5,5,8a- tetramethyl-7H- 1-benzopyran-7-ones (3,4-Dihydro-3-oxoedulans), J. Agric. Food Chem. 1995, 43, 1898-1902

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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