c

(-)-(3S,3aR)-Sedanolide - 99.9% ee - Natural celery leaf odor, herbal, and strong bitter. Odor threshold = 1.3x10-2 ppm (in 1% ethanol) The (3S,3aR)-isomer had the strongest odor, which was about 20 times stronger than the antipode and about 100 times stronger than the other two diastereomers = (-)-(3S,3aR)-3-butyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one or (-)-(3S,3aR)-3-butyl-3a,4,5,6-tetrahydro-2-benzofuran-1(3H)-one Ref: Daichi Oguro, Hidenori Watanabe, Synthesis and sensory evaluation of all stereoisomers of sedanolide, Tetrahedron, Volume 67, Issue 4, 28 January 2011, Pages 777-781

c

(+)-(3R,3aS)-Sedanolide - 99.4% ee - Celery seed odor, heavy, and spicy. Weak impression of celery. Odor threshold = 2.7x10-1 ppm (in 1% ethanol) = (+)-(3R,3aS)-3-butyl-3a,4,5,6-tetrahydroisobenzo-furan-1(3H)-one or (+)-(3R,3aS)-3-butyl-3a,4,5,6-tetrahydro-2-benzofuran-1(3H)-one Ref: Daichi Oguro, Hidenori Watanabe, Synthesis and sensory evaluation of all stereoisomers of sedanolide, Tetrahedron, Volume 67, Issue 4, 28 January 2011, Pages 777-781

(+)-(3R,3aR)-Sedanolide - 99.1% ee - Natural celery stem odor, herbal, and bitter.

Odor threshold = 1.6 ppm (in 1% ethanol)

= (+)-(3R,3aR)-3-butyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one or (+)-(3R,3aR)-3-butyl-3a,4,5,6-tetrahydro-2-benzofuran-1(3H)-one

Ref: Daichi Oguro, Hidenori Watanabe, Synthesis and sensory evaluation of all stereoisomers of sedanolide, Tetrahedron, Volume 67, Issue 4, 28 January 2011, Pages 777-781

(-)-(3S,3aS)-Sedanolide - 99.6% ee - Very weak odor. No impression of celery.

Odor threshold = 1.9 ppm (in 1% ethanol)

= (-)-(3S,3aS)-3-butyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one or (-)-(3S,3aS)-3-butyl-3a,4,5,6-tetrahydro-2-benzofuran-1(3H)-one

Ref: Daichi Oguro, Hidenori Watanabe, Synthesis and sensory evaluation of all stereoisomers of sedanolide, Tetrahedron, Volume 67, Issue 4, 28 January 2011, Pages 777-781

Ionones, Irones, Damascones & Structurally Related Odorants

Acyclics (Alcohols, Esters, Acids, Aldehydes)

Lactones

Sesquiterpenoid Related Odorants