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

The Aurantiols®

(Schiff base of Hydroxycitronellal & Methyl anthrainilate)

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Photo by permission of M. Roudintska - Art & Parfum

(3R)-(+)-Aurantiol - an orange flower fragrance that is not much different from those (prepared from) the other isomeric (d- or dl) forms of hydroxycitronellal, but a more irritating odor, less clean, and less (or none) of the green note as compared to the laevo form. (Yamamato)

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

Ref: 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; T. Yamamoto, K. Sakurai, S. Watanabe, A. Kinosaki, Perfume composition , U.S. Patent No. 4738951 (April 19, 1988)

Aurantiol is a tradename of Givaudan SA; also known as Auralva (IFF), Aurantesin (H&R, now Symrise), Aurantion (Quest, now Givaudan), Aurantha (Takasago)

(3S)-(-)-Aurantiol - an orange flower fragrance that is not much different from those (prepared from) the other isomeric (d- or dl) forms of hydroxycitronellal, but with a less irritating odor and imparts a clean and green note note as compared to the dextro or racemic forms; therefore, the impression of this substance was that it was of higher quality than the other forms. (Yamamato)

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

Ref: 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; T. Yamamoto, K. Sakurai, S. Watanabe, A. Kinosaki, Perfume composition , U.S. Patent No. 4738951 (April 19, 1988)

Aurantiol is a tradename of Givaudan SA; also known as Auralva (IFF), Aurantesin (H&R, now Symrise), Aurantion (Quest, now Givaudan), Aurantha (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

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