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

The Rosaphens

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Photo by permission of M. Roudintska - Art & Parfum

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(-)-(S)-Rosaphen, 95% ee - slightly citrus-like, fruity, aldehydic, citrus peel-like, pine terpene-like, powdery plum-like

= (-)-(2S)-2-methyl-5-phenylpentan-1-ol

The racemate was described as - fruity, brilliant, rosy, wine-like, honey, tea-like, geranyl acetate-like, sweet grapefruit-like.

Ref: Masashi Kawasaki, Naoki Toyooka, Tomoki Saka, Michimasa Goto, Yuji Matsuya, Tadashi Kometani, Lipase-mediated preparation of optically active isomers of Rosaphen®, Journal of Molecular Catalysis B: Enzymatic 67 (2010) 135–142; Dr. Yasuo Tanaka, Taiyo Koryo Corporation conducted the olfactory evaluation.

Rosaphen® is a tradename of Symrise

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(+)-(R)-Rosaphen, 96% ee - green tea-like, fatty, slightly fruity, heavy, green and citrus-like

= (+)-(2R)-2-methyl-5-phenylpentan-1-ol

Ref: Masashi Kawasaki, Naoki Toyooka, Tomoki Saka, Michimasa Goto, Yuji Matsuya, Tadashi Kometani, Lipase-mediated preparation of optically active isomers of Rosaphen®, Journal of Molecular Catalysis B: Enzymatic 67 (2010) 135–142; Dr. Yasuo Tanaka, Taiyo Koryo Corporation conducted the olfactory evaluation.

Rosaphen® is a tradename of Symrise

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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