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

The gamma-Jasmin lactones

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Photo by permission of M. Roudintska - Art & Parfum

(R)-(-)-(Z)-7-gamma-decenolactone - racemate-like, fruity, intensive peach-like, coconut, distinctly stronger than (S)-(+)- antipode; Bourdineaud et. al. describe this as: Exhibits a mild floral, lactonic and coumarine-like note. It is more intense than the S-(-)-enantiomer. Each of these two enantiomers is very ddifferent from the racemate, which is strongly fatty .

= (R)-(-)-gamma-jasmin lactone

Ref: P. Werkhoff et. al,. Z. Lebensm. Unters. Forsch. 196, 307-328 (1993); N. Fischer et. al., in Progress in Flavour Precursor Studies, P. Schreier and P. Winterhalter, eds, Int'l Symp. Univ. Wuerzburg, (Sept. 30-0ct. 2,1992), Carol Stream,Illinois, USA, Allured Publ, (1993) pp. 287-294; Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993; Bourdineaud, Jean-Paul; Ehret, Charles; Petrzilka, Martin; Optically active lactones, World Patent WO/94107887, April 19, 1994

(S)-(+)-(Z)-7-gamma-decenolactone - creamy, milky, soft, caramel, fruity gamma-decalactone-like, weakly peach-like; Bourdineaud et. al. describe this as: More heavy and lactonic, but less floral and mild than the (R)-(+)-enantiomer. Approaches rather a tuberose note, whereas the (S)-(+)-enantiomer tends towards jasmin. The (S)-(+)-enantiomer is organoleptically clearly less interesting than the (R)-(+)-enantiomer, but it is more tenacious and assures the coconut base of the racemate.

= (S)-(+)-gamma-jasmin lactone

Ref: P. Werkhoff et. al,. Z. Lebensm. Unters. Forsch. 196, 307-328 (1993); N. Fischer et. al., in Progress in Flavour Precursor Studies, P. Schreier and P. Winterhalter, eds, Int'l Symp. Univ. Wuerzburg, (Sept. 30-0ct. 2,1992), Carol Stream,Illinois, USA, Allured Publ, (1993) pp. 287-294; Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993; Bourdineaud, Jean-Paul; Ehret, Charles; Petrzilka, Martin; Optically active lactones, World Patent WO/94107887, April 19, 1994

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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