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

The Hydroxycitronellals

(Laurinals)

You must have Java installed to view the molecular visualization on this page
Photo by permission of M. Roudintska - Art & Parfum

(3R)-(+)-7-hydroxy-6,7-dihydrocitronellal - weak floral (liley-of the-valley) green, leaf-like and minty notes (Skorianetz et al.); also described as "powerful irritating, rosy, liley-of the-valley" (Yamamato)

The (R)-(+)-enantiomer is an allergen that restricts is usage in perfumes.

Ref: W. Skorianetz, H. Giger & G. Ohloff, Helv. Chim. Acta, 54,1797-1801 (1971); Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993; 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; S. Watanabe, S., Kinosaki, A., Kawasaki, M., Yoshida, T., and Kaidbey, K. H. The Contact Sensitizing Potential of (+)- and (-)-Hydroxycitronellal. In Flavors and fragrances: a world perspective. Proceedings of the 10th international congress of essential oils, fragrances and flavors, Washington, DC, USA, 16-20 November 1986, Editors: Lawrence, B. M. , Mookherjee, B. D., Willis, B. J., Elsevier ,1988, 1029-1038

Tradename = Laurinal (Takasago)

(3S)-(-)-7-hydroxy-6,7-dihydrocitronellal - fresh floral, sweet lily-of-the-valley notes (Skorianetz et al.); also described as "clean, green, lily-of-the-valley and is superior in fine fragrance to its (3R)-(+)- antipode" (Yamamato)

The (S)-(-)-enantiomer is much less allergeinic making its usage in perfumes preferable to the (R)-(+)-form.

Ref: W. Skorianetz, H. Giger & G. Ohloff, Helv. Chim. Acta, 54,1797-1801 (1971); Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993; 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; S. Watanabe, S., Kinosaki, A., Kawasaki, M., Yoshida, T., and Kaidbey, K. H. The Contact Sensitizing Potential of (+)- and (-)-Hydroxycitronellal. In Flavors and fragrances: a world perspective. Proceedings of the 10th international congress of essential oils, fragrances and flavors, Washington, DC, USA, 16-20 November 1986, Editors: Lawrence, B. M. , Mookherjee, B. D., Willis, B. J., Elsevier ,1988, 1029-1038

Tradename = l-Laurinal (Takasago)

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

HOME

Copyright 2001-2002 - Leffingwell & Associates