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

Doremox® enantiomers

The 4-methyl-2-phenyltetrahydro-2H-pyrans

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Photo by permission of M. Roudintska - Art & Parfum

(2R,4S)-cis-Doremox® (ee=92%) - rose oxide, diphenyl oxide, metallic, slightly plastic

= (2R,4S)-4-methyl-2-phenyltetrahydro-2H-pyran

Ref: Elisabetta Brenna, Claudio Fuganti, Sabrina Ronzani, and Stefano Serra, Biocatalyzed preparation of the optically enriched stereoisomers of 4-methyl-2-phenyl-tetrahydro-2H-pyran (Doremox®), Can. J. Chem., 80(6): 714-723 (2002); Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

Doremox® is a registered trademark of Firmenich SA

(2S,4R)-cis-Doremox® (ee=80%) - rose oxide, powerful, nice. The (2S,4R)-cis-enantiomer is, thus, the nicest and the most powerful isomer of the series. This stereoisomer, incidentally, has the same absolute configuration of the most appreciated of rose oxide isomers, i.e. (2S,4R)-cis-rose oxide

= (2S,4R)-4-methyl-2-phenyltetrahydro-2H-pyran

Ref: Elisabetta Brenna, Claudio Fuganti, Sabrina Ronzani, and Stefano Serra, Biocatalyzed preparation of the optically enriched stereoisomers of 4-methyl-2-phenyl-tetrahydro-2H-pyran (Doremox®), Can. J. Chem., 80(6): 714-723 (2002); Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

Doremox® is a registered trademark of Firmenich SA

(2R,4R)-trans-Doremox® (ee=50%) - rosy, rose oxide, metallic, off note

= (2R,4R)-4-methyl-2-phenyltetrahydro-2H-pyran

Ref: Elisabetta Brenna, Claudio Fuganti, Sabrina Ronzani, and Stefano Serra, Biocatalyzed preparation of the optically enriched stereoisomers of 4-methyl-2-phenyl-tetrahydro-2H-pyran (Doremox®), Can. J. Chem., 80(6): 714-723 (2002); Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

Doremox® is a registered trademark of Firmenich SA

(2S,4S)-trans-Doremox® (ee=72%) - weak, rosy, plastic, citronellol, a rose oxide note is also present.

= (2S,4S)-4-methyl-2-phenyltetrahydro-2H-pyran

Ref: Elisabetta Brenna, Claudio Fuganti, Sabrina Ronzani, and Stefano Serra, Biocatalyzed preparation of the optically enriched stereoisomers of 4-methyl-2-phenyl-tetrahydro-2H-pyran (Doremox®), Can. J. Chem., 80(6): 714-723 (2002); Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

Doremox® is a registered 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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