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

The Polysantols® [3,3-Dimethyl-5-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-penten-2-ols]

(Sandalwood odorants)

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Photo by permission of M. Roudintska - Art & Parfum

(-)-(1'R,2S,E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol - weaker and less characteristic sandalwood note than the (+)-(1'S,2S,E)-isomer but superior to the (+)-(1'S,2R,E)- or (-)-(1'R,2R,E)- isomers

= (-)-(1'R,2S,E)-Polysantol®

Ref: Chapuis, et al., United States Patent 5,512,543, April 30, 1996

Polysantol® is a trademark of Firmenich SA

(+)-(1'S,2R,E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol - ranked in 3d place of 4 isomers for its sandalwood odor

= (+)-(1'S,2R,E)- Polysantol®

Ref: Chapuis, et al., United States Patent 5,512,543, April 30, 1996

Polysantol® is a trademark of Firmenich SA

(-)-(1'R,2R,E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol - weakest and less characteristic sandalwood note than any of the other isomers

= (-)-(1'R,2R,E)- Polysantol®

Ref: Chapuis, et al., United States Patent 5,512,543, April 30, 1996

Polysantol® is a trademark of Firmenich SA

(+)-(1'S,2S,E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol - develops a sandalwood note of remarkable strength, wherein the typical milky character is represented at its best and accompanied by a slightly animal note; this is the preferred of four possible isomers

= (+)-(1'S,2S,E)- Polysantol®

Ref: Chapuis, et al., United States Patent 5,512,543, April 30, 1996

Polysantol® is a trademark of Firmenich SA

(+)-(2S,E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol - good characteristic sandalwood note

= (+)-(2S,E)- Polysantol®

Note that the C-1' position is epimeric, so this actually is a mixture of the (1'S, 2S,E) & (1'R,2S,E) isomers

Ref: Chapuis, et al., United States Patent 5,512,543, April 30, 1996

Polysantol® is a trademark of Firmenich SA

(-)-(2R,E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol - weaker and less characteristic sandalwood note

= (-)-(2R,E)- Polysantol®

Note that the C-1' position is epimeric, so this actually is a mixture of the (1'S, 2R,E) & (1'R,2R,E) isomers

Ref: Chapuis, et al., United States Patent 5,512,543, April 30, 1996

Polysantol® is a trademark of Firmenich SA

(-)-(1'R,E)-3,3-dimethyl-5-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-penten-2-ol - develops a sandalwood note, the character of which is strongly reminiscent of the typical milky odor of sandalwood; very distinctly different from the (-)-(1'R,E)- isomer.

= (-)-(1'R,E)-Polysantol®

Note that the C-2 position is epimeric, so this actually is a mixture of the (1'R, 2S,E) & (1'R,2R,E) isomers

Ref: Chapuis, et al., United States Patent 5,512,543, April 30, 1996

Polysantol® is a trademark of Firmenich SA

(+)-(1'S,E)-3,3-dimethyl-5-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-penten-2-ol is drier, more woody-cedar and less milky than that of its (-)-(1'R,E)- isomer; considered to be more powerful in odor strength than the (-)-(1'R,E)-isomer

= (+)-(1'S,E)- Polysantol®

Note that the C-2 position is epimeric, so this actually is a mixture of the (1'S, 2S,E) & (1'S,2R,E) isomers

Ref: Chapuis, et al., United States Patent 5,512,543, April 30, 1996

Polysantol® is a trademark of Firmenich 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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