(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)
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(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)
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