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

The alpha-Phellandrenes

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Photo by permission of M. Roudintska - Art & Parfum

(R)-(-)-alpha-phellandrene - terpene-like, medicinal

Odor Threshold = NA (in air)

Odor Threshold = 500 ppb in water

Ref: Blank, I., A. Sen, W. Grosch, Sensory study on the character-impact flavour compounds of dill herb (Anethum graveolens L.), Food Chem 43:337-343 (1992); Blank, I., W. Grosch, Evaluation of potent odorants in dill seed and dill herb (Anethum graveolens L.) by aroma extract dilution analysis, J Food Sci 56:63-67 (1991); Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Sensory Properties of Optical Isomers, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993; Koppenhoefer, B., R. Behnisch, U. Epperlein, H.a Holzschuh, A. Bernreuther, P. Piras and C. Roussel, Enantiomeric Odor Differences and Gas Chromatographic Properties of Flavors and Fragrances. A Selected Review. Perfumer & Flavorist, Vol. 19(5), 1-14 (1994)

(S)-(+)-alpha-phellandrene - characteristic dill note; also as weed-like, dill-like.

Odor Threshold = 700 ppb in air

Odor Threshold = 200 ppb in water

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: Blank, I., A. Sen, W. Grosch, Sensory study on the character-impact flavour compounds of dill herb (Anethum graveolens L.), Food Chem 43:337-343 (1992); Blank, I., W. Grosch, Evaluation of potent odorants in dill seed and dill herb (Anethum graveolens L.) by aroma extract dilution analysis, J Food Sci 56:63-67 (1991); Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Sensory Properties of Optical Isomers, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993; Koppenhoefer, B., R. Behnisch, U. Epperlein, H.a Holzschuh, A. Bernreuther, P. Piras and C. Roussel, Enantiomeric Odor Differences and Gas Chromatographic Properties of Flavors and Fragrances. A Selected Review. Perfumer & Flavorist, Vol. 19(5), 1-14 (1994)

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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