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

The Pamplefleur®s

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Photo by permission of M. Roudintska - Art & Parfum

(2R,4S)-Pamplefleur® (ee = 91%) - natural, fruity odor in the direction of grapefruit and rhubarb, close to Gardenol ('methyl phenyl carbinyl acetate") and 2,5-dimethyloct-2-en-6-one, slightly metallic

= (2R,4S)-2-methyl-4-phenylpentan-1-ol

Ref: Agnese Abate, Elisabetta Brenna, Claudio Fuganti, Francesco G. Gatti, Tommaso Giovenzana, Luciana Malpezzi, and Stefano Serra , Chirality and Fragrance Chemistry: Stereoisomers of the Commercial Chiral Odorants Muguesia and Pamplefleur, J. Org. Chem. 2005, 70, 1281-1290; Agnese Abate, Elisabetta Brenna, Claudio Fuganti, Francesco G. Gatti, Stefano Serra, Odor and (Bio)diversity: Single Enantiomers of Chiral Fragrant Substances, Chemistry & Biodiversity, Volume 1, Issue 12, Date: December 2004, Pages: 1888-1898

Pamplefleur® is a registered trademark of International Flavors & Fragrances

(2S,4R)-Pamplefleur® (ee = 92%) - fruity-citric odor, with some harsh,animalic, and slightly woody nuances, also abit rubbery

= (2S,4R)-2-methyl-4-phenylpentan-1-ol

Ref: Agnese Abate, Elisabetta Brenna, Claudio Fuganti, Francesco G. Gatti, Tommaso Giovenzana, Luciana Malpezzi, and Stefano Serra , Chirality and Fragrance Chemistry: Stereoisomers of the Commercial Chiral Odorants Muguesia and Pamplefleur, J. Org. Chem. 2005, 70, 1281-1290; Agnese Abate, Elisabetta Brenna, Claudio Fuganti, Francesco G. Gatti, Stefano Serra, Odor and (Bio)diversity: Single Enantiomers of Chiral Fragrant Substances, Chemistry & Biodiversity, Volume 1, Issue 12, Date: December 2004, Pages: 1888-1898

Pamplefleur® is a registered trademark of International Flavors & Fragrances

(2R,4R)-Pamplefleur® (ee = 92%) - floral-fruity odor in the direction of rhubarb with a touch of grapefruit, also reminiscent of Gardenol

= (2R,4R)-2-methyl-4-phenylpentan-1-ol

Ref: Agnese Abate, Elisabetta Brenna, Claudio Fuganti, Francesco G. Gatti, Tommaso Giovenzana, Luciana Malpezzi, and Stefano Serra , Chirality and Fragrance Chemistry: Stereoisomers of the Commercial Chiral Odorants Muguesia and Pamplefleur, J. Org. Chem. 2005, 70, 1281-1290; Agnese Abate, Elisabetta Brenna, Claudio Fuganti, Francesco G. Gatti, Stefano Serra, Odor and (Bio)diversity: Single Enantiomers of Chiral Fragrant Substances, Chemistry & Biodiversity, Volume 1, Issue 12, Date: December 2004, Pages: 1888-1898

Pamplefleur® is a registered trademark of International Flavors & Fragrances

(2S,4S)-Pamplefleur® (ee = 91%)- floral-fruity odor in the direction of grapefruit and linalool, with earthy, woody and bitter nuances, also reminiscent of 2,5-dimethyloct-2-en-6-one and of some aspects of veitiver oil

= (2S,4S)-2-methyl-4-phenylpentan-1-ol

Ref: Agnese Abate, Elisabetta Brenna, Claudio Fuganti, Francesco G. Gatti, Tommaso Giovenzana, Luciana Malpezzi, and Stefano Serra , Chirality and Fragrance Chemistry: Stereoisomers of the Commercial Chiral Odorants Muguesia and Pamplefleur, J. Org. Chem. 2005, 70, 1281-1290; Agnese Abate, Elisabetta Brenna, Claudio Fuganti, Francesco G. Gatti, Stefano Serra, Odor and (Bio)diversity: Single Enantiomers of Chiral Fragrant Substances, Chemistry & Biodiversity, Volume 1, Issue 12, Date: December 2004, Pages: 1888-1898

Pamplefleur® is a registered trademark of International Flavors & Fragrances

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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