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

The 4,5-epoxy-(E)-2-decenals

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Photo by permission of M. Roudintska - Art & Parfum

(4R,5R)-(-)-epoxy-(E)-2-decenal -

At 0.02 ppb in water - faint smell, mild metallic taste (strongest enantiomer)

At 0.2 ppb in water - strong metallic smell/taste

At 20 ppb in water - strong metallic and bean taste/smell

"The profile in all the samples is similar, with the (-) isomer at least 3-5 times stronger than the (+/-) racemate, or 10 times stronger than the (+) isomer."

Ref: Daniher, Andrew; Furrer, Stefan; Goeke, Andreas; Epoxydecenal isomers, United States Patent 6,335,047 (January 1, 2002)

 

 

(4S,5S)-(+)-epoxy-(E)-2-decenal -

At 0.02 ppb in water - no smell, no taste (weakest enantiomer)

At 0.2 ppb in water - mild metallic smell and taste

At 20 ppb in water - clear metallic and bean taste/smell

"The profile in all the samples is similar, with the (-) isomer at least 3-5 times stronger than the (+/-) racemate, or 10 times stronger than the (+) isomer."

Ref: Daniher, Andrew; Furrer, Stefan; Goeke, Andreas; Epoxydecenal isomers, United States Patent 6,335,047 (January 1, 2002)

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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Copyright 2001 - Leffingwell & Associates