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

The 2-Methyltetrahydrofuranthiol acetates

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Photo by permission of M. Roudintska - Art & Parfum

(2R,3R)-(+)-2-methyltetrahydrofuran-3-thiol acetate - raw garlic and onion-like, savory, musty, sulfurous

Odor threshold in air = 3.8 ng/L

= S-[(2R,3R)-(+)-2-methyltetrahydrofuran-3-yl] ethanethioate

= S-(2R,3R)-(+)-tetrahydro-2-methylfuran-3-yl ethanethioate

Ref: Yifeng Dai, Junqiang Shao, Shaoxiang Yang, Baoguo Sun, Yongguo Liu, Ting Ning, and Hongyu Tian, Enantioselective Syntheses and Sensory Properties of 2-Methyltetrahydrofuran-3-thiol Acetates, J. Agric. Food Chem. 2015, 63, 464-468.

(2S,3S)-(-)-2-methyltetrahydrofuran-3-thiol acetate - raw garlic and onion-like, sulfurous

Odor threshold in air = 5.7 ng/L

= S-[(2S,3S)-(-)-2-methyltetrahydrofuran-3-yl] ethanethioate

= S-(2S,3S)-(-)-tetrahydro-2-methylfuran-3-yl ethanethioate

Ref: Yifeng Dai, Junqiang Shao, Shaoxiang Yang, Baoguo Sun, Yongguo Liu, Ting Ning, and Hongyu Tian, Enantioselective Syntheses and Sensory Properties of 2-Methyltetrahydrofuran-3-thiol Acetates, J. Agric. Food Chem. 2015, 63, 464-468.

(2R,3S)-(+)-2-methyltetrahydrofuran-3-thiol acetate - meaty, sesame paste, fried onion and garlic, sweet, sulfurous

Odor threshold in air = 18.6 ng/L

= S-[(2R,3S)-(+)-2-methyltetrahydrofuran-3-yl] ethanethioate

= S-(2R,3S)-(+)-tetrahydro-2-methylfuran-3-yl ethanethioate

Ref: Yifeng Dai, Junqiang Shao, Shaoxiang Yang, Baoguo Sun, Yongguo Liu, Ting Ning, and Hongyu Tian, Enantioselective Syntheses and Sensory Properties of 2-Methyltetrahydrofuran-3-thiol Acetates, J. Agric. Food Chem. 2015, 63, 464-468.

 

(2S,3R)-(-)-2-methyltetrahydrofuran-3-thiol acetate - roasted meat, burnt, fried onion

Odor threshold in air = 7.3 ng/L

= S-[(2S,3R)-(-)-2-methyltetrahydrofuran-3-yl] ethanethioate

= S-(2S,3R)-(-)-tetrahydro-2-methylfuran-3-yl ethanethioate

Ref: Yifeng Dai, Junqiang Shao, Shaoxiang Yang, Baoguo Sun, Yongguo Liu, Ting Ning, and Hongyu Tian, Enantioselective Syntheses and Sensory Properties of 2-Methyltetrahydrofuran-3-thiol Acetates, J. Agric. Food Chem. 2015, 63, 464-468.

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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