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

The 4-Acetylthio-2-heptanols

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Photo by permission of M. Roudintska - Art & Parfum

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(2S,4R)-4-acetylthio-2-heptanol - grapefruit, refreshing (by GC-O)

Odor Threshold = 0.2 ng/L (air)

= S-[(2S,4R)-2-hydroxyheptan-4-yl] ethanethioate

Ref: Svenja Nörenberg, Bastian Reichardt, Verena Andelfinger, Wolfgang Eisenreich, and Karl-Heinz Engel, Influence of the Stereochemistry on the Sensory Properties of 4-Mercapto-2-heptanol and Its Acetyl-Derivatives, J. Agric. Food Chem., 2013, 61 (9), pp 2062–2069.

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(2R,4S)-4-acetylthio-2-heptanol - grapefruit, fruity, sweet (by GC-O)

Odor Threshold = 4.9 ng/L (air)

= S-[(2R,4S)-2-hydroxyheptan-4-yl] ethanethioate

Ref: Svenja Nörenberg, Bastian Reichardt, Verena Andelfinger, Wolfgang Eisenreich, and Karl-Heinz Engel, Influence of the Stereochemistry on the Sensory Properties of 4-Mercapto-2-heptanol and Its Acetyl-Derivatives, J. Agric. Food Chem., 2013, 61 (9), pp 2062–2069.

(2R,4R)-4-acetylthio-2-heptanol - savory, sweet (by GC-O)

Odor Threshold = 17.2 ng/L (air)

= S-[(2R,4R)-2-hydroxyheptan-4-yl] ethanethioate

Ref: Svenja Nörenberg, Bastian Reichardt, Verena Andelfinger, Wolfgang Eisenreich, and Karl-Heinz Engel, Influence of the Stereochemistry on the Sensory Properties of 4-Mercapto-2-heptanol and Its Acetyl-Derivatives, J. Agric. Food Chem., 2013, 61 (9), pp 2062–2069.

(2S,4S)-4-acetylthio-2-heptanol - sulfury, onion, sweet (by GC-O)

Odor Threshold = 0.03 ng/L (air)

= S-[(2S,4S)-2-hydroxyheptan-4-yl] ethanethioate

Ref: Svenja Nörenberg, Bastian Reichardt, Verena Andelfinger, Wolfgang Eisenreich, and Karl-Heinz Engel, Influence of the Stereochemistry on the Sensory Properties of 4-Mercapto-2-heptanol and Its Acetyl-Derivatives, J. Agric. Food Chem., 2013, 61 (9), pp 2062–2069.

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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