Process for the manufacturing of zeaxanthin from lutein

Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing

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C07C 3521

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057806934

ABSTRACT:
A process for the conversion of lutein or of its esters into zeaxanthin by base-catalyzed isomerization is disclosed. The process is carried out by heating an optionally pre-treated lutein-containing material in a mixture of an aqueous solution of an alkali hydroxide and either dimethyl sulphoxide or an organic solvent based on saturated aliphatic and/or aromatic hydrocarbons at temperatures in the range from about 50.degree. C. to about 120.degree. C. The process is carried out in the presence of a phase transfer catalyst when an organic solvent based on hydrocarbons is used. Being carotenoids, lutein and zeaxanthin are used correspondingly, especially as pigments for egg yolk, the integuments and the subcutaneous fat of poultry, the flesh and the integuments of fish and crustaceans, as well as foodstuffs. Zeaxanthin is preferably used in many applications, since in comparable dosages it produces a more intensive golden yellow pigmentation than lutein.

REFERENCES:
patent: 3523138 (1970-08-01), Grant
patent: 3535138 (1970-10-01), Wanmaker et al.
patent: 3783099 (1974-01-01), Matoushek
Jucker et al., Helv. Chim. Acta, 30: 266-267 (1947).
Kargl et al., "The Structure of .delta.-Carotene", Arch. Biochem. Biophys. 88:59-63 1960).
Zucker et al, ". . . ", Chimia 26, No. 3, pp.134-136 (1972).
A. G. Andrews, "Isomerization of .epsilon.-Carotene to .beta.-Carotene and of Lutein to Zeaxanthin", Acta. Chem. Scand. B 28, No. 1, pp. 137-138 (1974).
Quakenbush et al., "Composition and Analysts of the Carotenoids in Marigold Petals", Journal of the AOAC, vol. 55, No. 3, pp. 617-621 (1972).
Gau et al., "Mass Spectrometric Identification of Xanthophyll Fatty Acid Esters From Marigold Flowers (Tagetes Erecta)Obtained by High-Performance Liquid Chromatography and Craig Counter-Current Distribution", Journal of Chromatography 262:277-284 (1983).
Derwent Abstract No. 97-47053 of WO 97/31894.
Derwent Abstract No. 96-167352 of JP 8048895.

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