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

The 2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-pentenenitriles

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Photo by permission of M. Roudintska - Art & Parfum

(-)-(1'R,2R)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-pentenenitrile - citrus, fruity and fresh character accompanied by a sandalwood bottom character

Ref: Chapuis, et al., United States Patent 5,696,075, December 9, 1997

(+)-(1'S,2s)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-pentenenitrile - odor not described other than to say the (1'R)-isomers are preferred

Ref: Chapuis, et al., United States Patent 5,696,075, December 9, 1997

(+)-(1'S,2R)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-pentenenitrile - odor not specifically described other than to say the (1'R)-isomers are preferred

Ref: Chapuis, et al., United States Patent 5,696,075, December 9, 1997

(-)-(1'R,2S)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-pentenenitrile - a sandalwood odor wherein the desired fruity-citrus character of the (-)-(1'R,2R)-isomer is no longer present

Ref: Chapuis, et al., United States Patent 5,696,075, December 9, 1997

((-)-(1'R)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-pentenenitrile - a woody-citrus, fruity and slightly fatty odor preferred to the (+)-(1'S)-isomers

Note that the C-2 methyl group is epimeric and this actually is a mixture of the (1'R,2R) & (1'R,2S) isomers

Ref: Chapuis, et al., United States Patent 5,696,075, December 9, 1997

(+)-(1'S)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-pentenenitrile - odor not described except to say the preferred odor ar the (-)-(1'R)-isomers

Note that the C-2 methyl group is epimeric and this actually is a mixture of the (1'S,2R) & (1'S,2S) isomers

Ref: Chapuis, et al., United States Patent 5,696,075, December 9, 1997

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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