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

The cis-Dill Ethers

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Photo by permission of M. Roudintska - Art & Parfum

 

(3R,3aR,7aS)-Dill ether - Odor - faintly herbal, unspecific

Also known as: (3R,3aR,7aS)-3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran (3S,4R,8R)-3,9-epoxy-1-p-menthene

Ref: Sylvia Reichert, Matthias Wüst, Thomas Beck, Armin Mosandl, Stereoisomeric Flavor Compounds LXXXI: Dill Ether and Its cis-Stereoisomers: Synthesis and Enantioselective Analysis, J. High Resol. Chromatogr. 1998, 21 (3), 185-188; Sylvia Reichert, Armin Mosandl, Stereoisomeric Flavor Compounds LXXXII Dill Ether and Its Stereoisomers: Synthesis and Enantioselective Analysis, J. High Resol. Chromatogr. 1999, 22 (11), 631-634

 

(3S,3aS,7aR)-Dill ether - Odor - Dill; The naturally occurring dill ether - showed the typical odour of dill oil.

Also descibed as Ethereal, minty, floral, weak dill-like (Blank et al.)

Odor Perception Threshold = 25 ppb in water (retronasal)

Also known as: (3S,3aS,7aR)-3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran and (3R,4S,8S)-3,9-epoxy-1-p-menthene

In dill, (S)-(+)-alpha-Phellandrene was evaluated as the character-impact compound of the dill flavour which was rounded off by an additive effect of (3R,4S,8S)-3,9-epoxy-1-p-menthene (dill ether) (from the 1991 Annual Report Summary of the Deutsche Forschungsanstalt für Lebensmittelchemie at Technische Universitat München, Dr. Peter Schieberle - Director).

Ref: Sylvia Reichert, Matthias Wüst, Thomas Beck, Armin Mosandl, Stereoisomeric Flavor Compounds LXXXI: Dill Ether and Its cis-Stereoisomers: Synthesis and Enantioselective Analysis, J. High Resol. Chromatogr. 1998, 21 (3), 185-188; Sylvia Reichert, Armin Mosandl, Stereoisomeric Flavor Compounds LXXXII Dill Ether and Its Stereoisomers: Synthesis and Enantioselective Analysis, J. High Resol. Chromatogr. 1999, 22 (11), 631-634; Sensory study on the character-impact flavour compounds of dill herb (Anethum graveolens L.); 1991 Annual Report Summary of the Deutsche Forschungsanstalt für Lebensmittelchemie at Technische Universitat München (Dr. Peter Schieberle - Director); Imre Blank, Alina Sen & Werner Grosch, Sensory study on the character-impact flavour compounds of dill herb (Anethum graveolens L.), Food Chemistry 43 (1992) 337-343

 

(3S,3aR,7aS)-Dill ether - Odor - herbal, sweet

Also known as: (3S,3aR,7aS)-3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran and (3S,4R,8S)-3,9-epoxy-1-p-menthene

Ref: Sylvia Reichert, Matthias Wüst, Thomas Beck, Armin Mosandl, Stereoisomeric Flavor Compounds LXXXI: Dill Ether and Its cis-Stereoisomers: Synthesis and Enantioselective Analysis, J. High Resol. Chromatogr. 1998, 21 (3), 185-188; Sylvia Reichert, Armin Mosandl, Stereoisomeric Flavor Compounds LXXXII Dill Ether and Its Stereoisomers: Synthesis and Enantioselective Analysis, J. High Resol. Chromatogr. 1999, 22 (11), 631-634

 

(3R,3aS,7aR)-Dill ether - Odor - fruity-sweet

Also known as: (3R,3aS,7aR)-3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran and (3R,4S,8R)-3,9-epoxy-1-p-menthene

Ref: Sylvia Reichert, Matthias Wüst, Thomas Beck, Armin Mosandl, Stereoisomeric Flavor Compounds LXXXI: Dill Ether and Its cis-Stereoisomers: Synthesis and Enantioselective Analysis, J. High Resol. Chromatogr. 1998, 21 (3), 185-188; Sylvia Reichert, Armin Mosandl, Stereoisomeric Flavor Compounds LXXXII Dill Ether and Its Stereoisomers: Synthesis and Enantioselective Analysis, J. High Resol. Chromatogr. 1999, 22 (11), 631-634

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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