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

The 3-Butylphthalides

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Photo by permission of M. Roudintska - Art & Parfum

(3R)-Butylphthalide - Herbaceous, celery-like odor; typical for the odor of celery and celeriac This enantiomer shows a significantly higher (>100 X) GC odour threshold value than does the (3S)-enantiomer.

Odor Threshold = 10 ng

Ref: Dietmar Bartschat, Birgit Maas, Sabine Smietana, Armin Mosandl, Stereoisomeric Flavour Compounds LXXIII: 3-Butylphthalide: Chirospecific Analysis, Structure and Properties of the Enantiomers, Phytochemical Analysis, 7(3), 131-135 (1996); Odor description from Leffingwell, Flavor-Base 2001

(3S)-Butylphthalide - Herbaceous, celery-like odor; This enantiomer shows a significantly lower (>100 X) GC odour threshold value than does the (3R)-enantiomer.

Odor Threshold = 0.01 ng

Mosandl's investigation of the essential oil of celery seed show enantiomeric distributions in the range of 95:5 in favour of the (3S)-enantiomer

Ref: Dietmar Bartschat, Birgit Maas, Sabine Smietana, Armin Mosandl, Stereoisomeric Flavour Compounds LXXIII: 3-Butylphthalide: Chirospecific Analysis, Structure and Properties of the Enantiomers, Phytochemical Analysis, 7(3), 131-135 (1996); Odor description from Leffingwell, Flavor-Base 2001

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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