US5780693A
Expired / Lapsed
US
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Process for the manufacturing of zeaxanthin from lutein
Assignee: F Hoffmann La Roche AG
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Filing: 1997-09-22
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Granted: 1998-07-14
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Expires: 2017-09-22
Abstract
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 DEG C. to about 120 DEG 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.
Inventors
- 👤 Kurt Bernhard
- 👤 Alfred Giger
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 20:35
CPC Classifications
C; C07; C07C; C07C403/00; C07C403/24; C09; C09B; C09B61/00
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
125 words
A process for the production of zeaxanthin from lutein or an ester thereof which process comprises heating a mixture which contains: a) a lutein-containing material comprising lutein or an ester thereof, b) an aqueous solution of an alkali hydroxide wherein the alkali hydroxide is present in the solution at a concentration of at least 3M, and c) a solvent selected from the group consisting of dimethyl sulphoxide and a liquid aliphatic or aromatic hydrocarbon, at a temperature in the range from about 50° C. to about 120° C., whereby said zeaxanthin is produced from said lutein or ester thereof, with the proviso that when the solvent is the liquid aliphatic or aromatic hydrocarbon, the mixture further comprises an effective amount of a phase transfer catalyst.
Claim 2
Dependent Claim
125 words
A process for the production of zeaxanthin from lutein or an ester thereof which process comprises heating a mixture which contains: a) a lutein-containing material comprising lutein or an ester thereof, b) an aqueous solution of an alkali hydroxide wherein the alkali hydroxide is present in the solution at a concentration of at least 3M, and c) a solvent selected from the group consisting of dimethyl sulphoxide and a liquid aliphatic or aromatic hydrocarbon, at a temperature in the range from about 50° C. to about 120° C., whereby said zeaxanthin is produced from said lutein or ester thereof, with the proviso that when the solvent is the liquid aliphatic or aromatic hydrocarbon, the mixture further comprises an effective amount of a phase transfer catalyst.
Claim 3
Dependent Claim
11 words
The process of claim 1 wherein the solvent is dimethyl sulphoxide.
Claim 4
Dependent Claim
83 words
The process of claim 2 wherein the alkali hydroxide is present in the mixture in an amount from about 10 to about 450 moles per mole of xanthophyll in the lutein-containing material, the ratio of the volume of the dimethyl sulphoxide to the volume of the alkali hydroxide solution is from about 4:1 to about 1:2, and the total volume of the dimethyl sulphoxide and alkali hydroxide solution is in the range from about 5 to 30 ml per gram of lutein-containing material.
Claim 5
Dependent Claim
83 words
The process of claim 3 wherein the alkali hydroxide is present in the mixture in an amount from about 200 to about 250 moles per mole of xanthophylls in said lutein-containing material, the ratio of the volume of the dimethyl sulphoxide to the volume of the alkali hydroxide solution is from about 2.5:1 to about 1:1, and the total volume of the dimethyl sulphoxide and alkali hydroxide solution is in the range from about 6 to 8 ml per gram of lutein-containing material.
Claim 6
Dependent Claim
47 words
The process of claim 4 herein the concentration of the alkali hydroxide in the alkali hydroxide solution is in the range from about 7M to about 14M, and the heating is carried out at a temperature in the range from about 80° C. to about 100° C.
Claim 7
Dependent Claim
20 words
The process of claim 5 wherein the lutein-containing material is an extract of the yellow or orange blossoms of marigolds.
Claim 8
Dependent Claim
12 words
The process of claim 6 wherein the alkali hydroxide is sodium hydroxide.
Claim 9
Dependent Claim
12 words
The process of claim 6 wherein the alkali hydroxide is potassium hydroxide.
Claim 10
Dependent Claim
15 words
The process of claim 1 wherein the solvent is a liquid aliphatic or aromatic hydrocarbon.
Claim 11
Dependent Claim
108 words
The process of claim 9 wherein the alkali hydroxide is present in the mixture in an amount from about 10 to about 450 moles per mole of xanthophyll in the lutein-containing material, the phase transfer catalyst is present in the mixture in an amount from about 0.5 to about 5 moles per mole of xanthophyll in the lutein-containing material, the ratio of the volume of the solvent to the volume of the alkali hydroxide solution is from about 8:1 to about 1:2, and the total volume of the solvent and alkali hydroxide solution is in the range from about 5 to 30 ml per gram of lutein-containing material.
Claim 12
Dependent Claim
106 words
The claim 10 wherein the alkali hydroxide is present in the mixture in an amount from about 200 to about 250 moles per mole of xanthophylls in said lutein-containing material, the phase transfer catalyst is present in the mixture in an amount from about 0.5 to about 1.5 moles per mole of xanthophyll in the lutein-containing material, the ratio of the volume of the solvent to the volume of the alkali hydroxide solution is from about 4:1 to about 1:1, and the total volume of the solvent and alkali hydroxide solution is in the range from about 6 to 8 ml per gram of lutein-containing material.
Claim 13
Dependent Claim
48 words
The process of claim 11 wherein the concentration of the alkali hydroxide in the akali hydroxide solution is in the range from about 7M to about 14 M, and the heating is carried out at a temperature in the range from about 80° C to about 100° C.
Claim 14
Dependent Claim
20 words
The process of claim 12 wherein the lutein-containing material is an extract of the yellow or orange blossoms of marigolds.
Claim 15
Dependent Claim
35 words
The process of claim 13 wherein the solvent is pentane, hexane, heptane, petroleum ether, benzene or toluene, and the phase transfer catalyst is tricaprylmethylammonium chloride, tetra(n-butyl)ammonium hydrogen sulphate, benzalkonium chloride, benzyltri(n-butyl)ammonium bromide and tri(n-butyl)methylammonium iodide.
Claim 16
Dependent Claim
24 words
The process of claim 14 wherein the solvent is hexane, heptane or high boiling petroleum ether and the phase transfer catalyst is tricaprylmethylammonium chloride.
Claim 17
Dependent Claim
12 words
The process of claim 15 wherein the alkali hydroxide is sodium hydroxide.
Claim 18
Dependent Claim
12 words
The process of claim 15 wherein the alkali hydroxide is potassium hydroxide.
References Cited (Backward Citations)
GB1046658A
Cited
US3523138A
Cited
US3535138A
Cited
US3783099A
Cited
WO1996002594A2
Cited
WO1997031894A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 2001-07-13 | 2002-01-12 | 2002-07-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2005-07-13 | 2006-01-12 | 2006-07-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2009-07-13 | 2010-01-12 | 2010-07-14 | $7700.00 | Window Closed / Lapsed |