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

The Nectaryls

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Photo by permission of M. Roudintska - Art & Parfum

(2S,2'R,1''R)-Nectaryl - Rather weak and uncharacteristic fruity-lactonic odour with some additional resemblance of green apple, it does not contribute much to the commercial Nectaryl.

Odour threshold: 11.2 ng/L air.

Note that the chiral carbons at positions 2 and 2' are enantiomeric, but the 1''R is not for this pair - thus while partially enantiomeric this pair are actually diastereomers

= (2S)-2-{(2R)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propyl}cyclopentanone

Ref: Elisabetta Brenna, Claudio Fuganti, Francesco G. Gatti, Luciana Malpezzi and Stefano Serra, Synthesis and olfactory evaluation of all stereoisomers of the fragrance Nectaryl. Tetrahedron: Asymmetry 19 (2008) 800–807

Nectaryl is a tradename of Givaudan SA

(2R,2'S,1''R)-Nectaryl - Powerful, very intense, sweet and dry fruity-lactonic odour in the direction of peach and apricots, with some floral undertone, does contribute much to the overall odour of commercial Nectaryl.

Odour threshold: 0.094 ng/L air.

Note that the chiral carbons at positions 2 and 2' are enantiomeric, but the 1''R is not for this pair - thus while partially enantiomeric this pair are actually diastereomers

= (2R)-2-{(2S)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propyl}cyclopentanone

Ref: Elisabetta Brenna, Claudio Fuganti, Francesco G. Gatti, Luciana Malpezzi and Stefano Serra, Synthesis and olfactory evaluation of all stereoisomers of the fragrance Nectaryl. Tetrahedron: Asymmetry 19 (2008) 800–807

Nectaryl is a tradename of Givaudan SA

(2S,2'S,1''R)-Nectaryl - Rather weak and uncharacteristic fruity-lactonic odour with some additional resemblance of green apple, it does not contribute much to the commercial Nectaryl.

Odour threshold: 14.9 ng/L air.

Note that the chiral carbons at positions 2 and 2' are enantiomeric, but the 1''R is not for this pair - thus while partially enantiomeric this pair are actually diastereomers

= (2S)-2-{(2S)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propyl}cyclopentanone

Ref: Elisabetta Brenna, Claudio Fuganti, Francesco G. Gatti, Luciana Malpezzi and Stefano Serra, Synthesis and olfactory evaluation of all stereoisomers of the fragrance Nectaryl. Tetrahedron: Asymmetry 19 (2008) 800–807

Nectaryl is a tradename of Givaudan SA

(2R,2'R,1''R)-nectaryl - Powerful, very intense, sweet and dry fruity-lactonic odour in the direction of peach and apricots, with some floral undertone, does contribute much to the overall odour of commercial Nectaryl.

Odour threshold: 0.112 ng/L air.

Note that the chiral carbons at positions 2 and 2' are enantiomeric, but the 1''R is not for this pair - thus while partially enantiomeric this pair are actually diastereomers

= (2R)-2-{(2R)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propyl}cyclopentanone

Ref: Elisabetta Brenna, Claudio Fuganti, Francesco G. Gatti, Luciana Malpezzi and Stefano Serra, Synthesis and olfactory evaluation of all stereoisomers of the fragrance Nectaryl. Tetrahedron: Asymmetry 19 (2008) 800–807

Nectaryl is a tradename of Givaudan SA

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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