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

The Lilials®

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Photo by permission of M. Roudintska - Art & Parfum

(S)-(+)-Lilial® - lily of the valley odor but slightly less strong than the (R)-(-)-isomer; also described as "aldehydic, chemical" (Yamamoto)

Ref: Georg Frater, et. al., Tetrahedron, 54, 7633-7703 (1998); D. Enders & H. Dyker, Liebigs Ann. Chem., 1107-1110 (1990). See also, Fumiko Yoshii, Tomoko Nakamura, Shuichi Hirono, Yumiko Shimizu,Takashi Hoshi, Masayoshi Ando, and Hisahiro Hagiwara, Conformational Analysis and Selection of Odor-Active Conformers: Synthesis of Molecules Designed for the Lily-of-the-Valley (Muguet)-Type Odor, Helvetica Chimica Acta, Vol. 84 (2001) pp. 2051-2063 and Dietmar Bartschat, Susanne Börner, A. Mosandl and Jan W. Bats, Stereoisomeric flavour compounds LXXVI: direct enantioseparation, structure elucidation and structure-function relationship of 4-tert-butyl-alpha-methyldihydrocinnamaldehyde, Zeitschrift für Lebensmitteluntersuchung, Volume 205 Issue 1 (1997) pp 76-79; T. Yamamato, Advances in the transition metal (Rh, Ru)-BINAP-catalyzed asymmetric chiral compounds for flavours and fragrances and their associated sensory properties, in Current Topics in Flavours and Fragrances - Towards a New Millennium of Discovery, Karl A. D. Swift, Ed., Kluwer Academic Publishers (now Springer), 2000, pp. 33-59, Note that the odor description is based on the (+)-enantiomer as Yamamoto's assignment of the (S) configuration has been reversed.

Lilial® is a registered trademark of Givaudan SA

Also known as Lilestralis (AFC), Lysmeral (BASF), Lilialdehyde (Kuraray).

(R)-(-)-Lilial®- lily of the valley odor but slightly stronger odor than the (S)-(+)-isomer; also described as "floral, oily, lily-of-the valley" (Yamamoto)

Ref: Georg Frater, et. al., Tetrahedron, 54, 7633-7703 (1998); D. Enders & H. Dyker, Liebigs Ann. Chem., 1107-1110 (1990). See also, Fumiko Yoshii, Tomoko Nakamura, Shuichi Hirono, Yumiko Shimizu,Takashi Hoshi, Masayoshi Ando, and Hisahiro Hagiwara, Conformational Analysis and Selection of Odor-Active Conformers: Synthesis of Molecules Designed for the Lily-of-the-Valley (Muguet)-Type Odor, Helvetica Chimica Acta, Vol. 84 (2001) pp. 2051-2063 and Dietmar Bartschat, Susanne Börner, A. Mosandl and Jan W. Bats, Stereoisomeric flavour compounds LXXVI: direct enantioseparation, structure elucidation and structure-function relationship of 4-tert-butyl-alpha-methyldihydrocinnamaldehyde, Zeitschrift für Lebensmitteluntersuchung, Volume 205 Issue 1 (1997) pp 76-79; T. Yamamato, Advances in the transition metal (Rh, Ru)-BINAP-catalyzed asymmetric chiral compounds for flavours and fragrances and their associated sensory properties, in Current Topics in Flavours and Fragrances - Towards a New Millennium of Discovery, Karl A. D. Swift, Ed., Kluwer Academic Publishers (now Springer), 2000, pp. 33-59, Note that the odor description is based on the (-)-enantiomer as Yamamoto's assignment of the (R) configuration has been reversed.

Lilial® is a registered trademark of Givaudan SA

Also known as Lilestralis (AFC), Lysmeral (BASF), Lilialdehyde (Kuraray).

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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