C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
C07C 29/60 (2006.01) C07C 29/00 (2006.01) C07C 29/17 (2006.01) C07C 29/56 (2006.01) C07C 29/78 (2006.01) C07C 35/21 (2006.01) C07C 41/09 (2006.01) C07C 43/196 (2006.01) C07B 61/00 (2006.01)
Patent
CA 2474646
The present invention relates to a method of reacting (3R,3'R,6'R)-lutein with a catalytic amount of an acid to obtain a mixture of anhydroluteins, rich in anhydrolutein III, with substantially no Z-isomers being formed. The mixture is converted to (3R)-.beta.-cryptoxanthin (major product) and (3R,6'R)-.alpha.- cryptoxanthin (minor product) by reacting the anhydroluteins with borane-amine complexes (e.g. Me3N.BH3) or other hydride donors and an acid in a chlorinated solvent, preferably dichloromethane, at ambient temperature to produce (3R)- .beta.-cryptoxanthin and (3R,6'R)-.alpha.-cryptoxanthin.
L'invention concerne un procédé faisant réagir (3R,3'R,6'R)-lutéine avec une quantité catalytique d'un acide pour obtenir un mélange d'anhydrolutéines, riches en anhydrolutéine III, avec sensiblement aucune formation de Z-isomères. Ledit mélange est transformé en (3R)-.beta.-cryptoxanthine (produit majeur) et (3R,6'R)-.alpha.-cryptoxanthine (produit mineur) par réaction des anhydrolutéines avec des complexes de amine-borane (par exemple Me¿3?N.BH¿3?) ou d'autres donneurs d'hydrure et un acide dans un solvant chloré, de préférence le dichlorométhane, à la température ambiante pour produire (3R)-.beta.-cryptoxanthine et (3R,6'R)-.alpha.-cryptoxanthine.
Osler Hoskin & Harcourt Llp
University Of Maryland College Park
LandOfFree
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