The delta-Octathionolactones

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

The 3-Mercaptoheptyl acetates

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Photo by permission of M. Roudintska - Art & Parfum

(3R)-(-)-3-mercaptoheptyl acetate - Escher et al. indicate that 3-mercaptoheptyl acetate (as the racemate) possesses a relatively weak top note reminding of a peach, citrus and tea tonality. This top note is followed by highly appreciated and performing bottom notes of the green/black tea type as well as of the citrus-grapefruit and fruity-pear-peach type which render said compound a very useful flavoring ingredient.

Liang et al. describe the racemate as sulfurous, sweet, fruity (on a smelling strip).

 Ref: Sina Dorothea Escher, Yvan Niclass Lionel Saudan, Thiols as Flavouring Agents, PCT WO2006120625 (November 16, 2006); Sen Liang, Baoguo Sun, Shaoxiang Yang, Yongguo Liu, Hongyu Tian, Yuping Liu, and Haitao Chen. "Preparation and odour properties of (S)-3-mercapto-1-heptyl acetate." Journal of Chemical Research 38, no. 6 (2014): 343-346.

 

 

(3S)-(+)-3-mercaptoheptyl acetate - The two enantiomers of the cited acetate, namely the (R) and the (S) ones, are also valuable flavoring ingredients, which can be used in a similar way. Amongst said enantiomers the most appreciated is the (S) one, which has a taste very close to the one of the racemate, although its grapefruit type note is weaker than the one of the racemate.

Liang et al. describe (3S)-(+)-3-mercaptoheptyl acetate as follows - The odour properties were evaluated by chiral GC-O. It possessed a tropical fruit aroma reminiscent of mango and passion fruit, with berry, ester-like, sweet, and pepper-like aspects.

 Ref: Sina Dorothea Escher, Yvan Niclass Lionel Saudan, Thiols as Flavouring Agents, PCT WO2006120625 (November 16, 2006); Sen Liang, Baoguo Sun, Shaoxiang Yang, Yongguo Liu, Hongyu Tian, Yuping Liu, and Haitao Chen. "Preparation and odour properties of (S)-3-mercapto-1-heptyl acetate." Journal of Chemical Research 38, no. 6 (2014): 343-346.

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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