Isomerization process

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters

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562510, 564191, 568443, 568668, 568824, C07C 6974, C07C 6122, C07C 6230

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active

059089571

ABSTRACT:
A process is disclosed for the catalyzed isomerization of a Z-isomer of a vitamin A compound or of a mixture of several of such isomers into a mixture of the corresponding all-E- and 13-Z-isomers of this vitamin A compound. The process utilizes nitrogen monoxide or a gas mixture containing nitrogen monoxide as the isomerization catalyst. Vitamin A acetate or vitamin A acid is preferably used as the vitamin A compound. The thus-produced all-E vitamin A and its alkanoyl esters have of all isomers by far the highest biological activity and are accordingly almost exclusively used in human and animal nutrition. The 13-Z-vitamin A compounds in turn play an important role as pharmaceutically active substances.

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Chernysh et al., Mechanism of the . . . vitamin A acetate, Zh. Org. Khim. vol. 11(7), pp. 1400-1403, 1975.
Mulry et al., Isomerization of retinyl . . . solvents, J. Assoc. Off. Anal. Chem. vol. 66 (3), pp. 746-750, 1983.
Lukton et al., On the Amine-Catalyzed . . . Aldehydes, J. Am. Chem. Soc. vol. 106, pp. 258-259, Jan. 1984.
Derwent Abstract of Japanese Patent No. 05 009 482 A, Nov. 9, 1993.
E. L. Eliel, Stereochemie der Kohlenstoffverbindungen, pp. 410-415, (1966).
Abstract of German Patent Specification 1 468 798, Nov. 19, 1970.

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