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

The Methylpropyloxathianes

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Photo by permission of M. Roudintska - Art & Parfum

(2S,4R)-(+)-cis-2-methyl-4-propyl.-1,3-oxathiane - sulfurous, fatty, fruity-green, tropical fruits, grapefruits; described by Ohloff sulfury note of tropical fruits

Odor Threshold = 2 ppb

Ref: W. Pickenhagen and H. Bronner-Schindler, Helv. Chim. Acta, 87,947-952 (1984); A. Mosandl and G. Heusinger, Liebigs Ann. Chem. 1185-1191 (1985); Gabriele Singer, Georg Heusinger, Otmar Frohlich, Peter Schreier, and Armin Mosandl, Chirality Evaluation of 2-Methyl-4-propyl-l,3-oxathiane from the Yellow Passion Fruit, J. Agric. Food Chem., Vol. 34, No. 6, 1029-1033 (1986); G. Ohloff, Scent & Fragrances, Springer-Verlag (1994), p. 43; Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993

(2R,4S)-(-)-cis-2-methyl-4-propyl.-1,3-oxathiane - sulfurous, herbaceous-green, roasty, linseed oil-like, onion; described by Ohloff as fresh, floral, less sulfury than the 2S,4R-isomer

Odor Threshold = 4 ppb

Ref: W. Pickenhagen and H. Bronner-Schindler, Helv. Chim. Acta, 87,947-952 (1984); A. Mosandl and G. Heusinger, Liebigs Ann. Chem. 1185-1191 (1985); Gabriele Singer, Georg Heusinger, Otmar Frohlich, Peter Schreier, and Armin Mosandl, Chirality Evaluation of 2-Methyl-4-propyl-l,3-oxathiane from the Yellow Passion Fruit, J. Agric. Food Chem., Vol. 34, No. 6, 1029-1033 (1986); G. Ohloff, Scent & Fragrances, Springer-Verlag (1994), p. 43; Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993

(2S,4S)-(+)-trans-2-methyl-4-propyl.-1,3-oxathiane - sulfurous, slight bloomy-sweet

Ref: Gabriele Singer, Georg Heusinger, Otmar Frohlich, Peter Schreier, and Armin Mosandl, Chirality Evaluation of 2-Methyl-4-propyl-l,3-oxathiane from the Yellow Passion Fruit, J. Agric. Food Chem., Vol. 34, No. 6, 1029-1033 (1986); A. Mosandl, W. Deger, M. Gessner, C. Gunther, G. Heusinger and G. Singer, Lebensmittelchem Gerichtl Chem., 41, 35 (1987); Bernhard Koppenhoefer, et. al., Perfumer & Flavorist, Vol. 19, No. 5, 1-14 (1994)

(2R,4R)-(–)-trans-2-methyl-4-propyl.-1,3-oxathiane - green grass, root, earthy, red radish note

Ref: A. Gabriele Singer, Georg Heusinger, Otmar Frohlich, Peter Schreier, and Armin Mosandl, Chirality Evaluation of 2-Methyl-4-propyl-l,3-oxathiane from the Yellow Passion Fruit, J. Agric. Food Chem., Vol. 34, No. 6, 1029-1033 (1986); Mosandl, W. Deger, M. Gessner, C. Gunther, G. Heusinger and G. Singer, Lebensmittelchem Gerichtl Chem., 41, 35 (1987); Bernhard Koppenhoefer, et. al., Perfumer & Flavorist, Vol. 19, No. 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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