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

The 2-Hexyl-4-acetoxytetrahydrofurans

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Photo by permission of M. Roudintska - Art & Parfum

(-)-(2S,4R)-cis-2-Hexyl-4-acetoxytetrahydrofuran - Odor - A strong sweet, alcoholic odour with weak milk-like note

Flavor dilution factor = 128

= (3R,5S)-5-hexyltetrahydrofuran-3-yl acetate

Ref: Guoying Zhang, Xiuqin Gong, Shaoxiang Yang, Baoguo Sun, Yongguo Liu and Hongyu Tian, Preparation and odour properties of the four stereoisomers of 2-hexyl-4-acetoxytetrahydrofuran, Flavour Fragr. J. 29: 349–354.

(+)-(2R,4S)-cis-2-Hexyl-4-acetoxytetrahydrofuran - Odor - A weak burnt woody, sour odour with faint sweet onion-like note

Flavor dilution factor = 16

= (3S,5R)-5-hexyltetrahydrofuran-3-yl acetate

Ref: Guoying Zhang, Xiuqin Gong, Shaoxiang Yang, Baoguo Sun, Yongguo Liu and Hongyu Tian, Preparation and odour properties of the four stereoisomers of 2-hexyl-4-acetoxytetrahydrofuran, Flavour Fragr. J. 29: 349–354.

(-)-(2R,4R)-trans-2-Hexyl-4-acetoxytetrahydrofuran - Odor - A fresh fruity, sweet, sour odour with weak garlic-like note

Flavor dilution factor = 64

= (3R,5R)-5-hexyltetrahydrofuran-3-yl acetate

Ref: Guoying Zhang, Xiuqin Gong, Shaoxiang Yang, Baoguo Sun, Yongguo Liu and Hongyu Tian, Preparation and odour properties of the four stereoisomers of 2-hexyl-4-acetoxytetrahydrofuran, Flavour Fragr. J. 29: 349–354.

(+)-(2S,4S)-trans-2-Hexyl-4-acetoxytetrahydrofuran - Odor - A cooling, sweet odour with faint sour, fruity note

Flavor dilution factor = 32

= (3S,5S)-5-hexyltetrahydrofuran-3-yl acetate

Ref: Guoying Zhang, Xiuqin Gong, Shaoxiang Yang, Baoguo Sun, Yongguo Liu and Hongyu Tian, Preparation and odour properties of the four stereoisomers of 2-hexyl-4-acetoxytetrahydrofuran, Flavour Fragr. J. 29: 349–354.

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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