Lutein to zeaxanthin isomerization process and product

Details Lutein to zeaxanthin isomerization process and product Lutein to zeaxanthin isomerization process and product

1998-10-29

2002-04-23

Vollano, Jean F. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

C568S823000, C568S834000, C568S832000, C568S822000

Reexamination Certificate

active

06376722

ABSTRACT:

FIELD OF THE INVENTION
The present invention is related to the obtainment of natural pigments from plant materials for use as food additives and, more particularly, it is related to a lutein to zeaxanthin isomerization process and to the product obtained with the same.
DESCRIPTION OF THE PRIOR ART
As consciousness towards the potential harm caused by some synthetic pigments previously used in foodstuffs for humans and animals is awakening throughout the world, the use of natural plant pigments has acquired more and more importance. It is because of this reason that extraction of colorants from natural sources such as flowers and fruits has been carried out for a long time all over the world.
In the Book “Colorantes Naturales de Mexico”, published by Industrias Resistol S. A. in 1988, several extraction methods of “flower dyes” are described, which comprise steps such as milling or boiling flower petals, and further addition of substances such as 96° ethyl alcohol, alum and vinegar solutions. This book also describes a vast plurality of different applications of several colorants of natural origin.
Among such applications and particularly in the poultry industry, the yellow color of egg yolk and broiler skin is originated by the pigments contained in the feed these birds ingest. The importance of pigmentation is that a good pigmentation in the birds is associated with a good condition and high quality during the breeding of the broilers, which has become an essential factor for the chicken and egg commercialization.
The main compounds associated with skin pigmentation in broilers and egg yolk pigmentation in laying hens (as well as in other species like fishes and crustaceans) are the so-called carotenoids, which are related to carotene in its chemical structure. The main carotenoids associated with pigmentation in poultry industry are denominated, in general terms, as xanthophylls (from Greek roots: Xanthos=Yellow; and Phylos=friend, lover). Xanthophylls have the common characteristic of being water insoluble pigments that are slightly soluble in ethyl alcohol and ether.
These carotenoids are generally found in natural products such as alfalfa, corn gluten, marigold flower and chili, among others.
Traditional sources of xanthophylls involved in poultry pigmentation have been alfalfa and corn gluten, in which carotenoids are found in their free form.
Market demand has compelled aviculturists to intensify the pigmentation level in their products, thus compelling also the natural pigment industry to carry out research and development activities for finding alternative natural sources of carotenoids. Marigold flower (
Tagetes erecta
) has become a viable alternative for these purposes due to its high xanthophyll content, although these compounds are found in its esterified form therein.
Nowadays, marigold flower yellow pigments and pigments from other plant sources are commercialized in its saponified form and formulated in different solid or liquid vehicles. Such pigments have been used for more than four decades as food additives, mainly as colorants for skin pigmentation in broilers and egg yolk pigmentation in laying hens. Saponification of said yellow pigments is necessary to facilitate their absorption and assimilation by the birds, inasmuch as these pigments, which are in their esterified form, are hydrolyzed or converted into their free form after saponification, thus being absorbed by the birds more rapidly and efficiently.
In the Poultry Science journal, pages 1708 to 1714, volume 65 of 1986, an article by D. L. Fletcher et al was published, in which the effect of saponification of marigold flower extracts and their pigmenting capacity in egg yolk and broiler skin is analyzed.
In industry, pigment extraction from marigold flower, as well as from other plant varieties, is traditionally carried out by means of different kinds of solvents to form concentrated extracts containing carotenoids in the esterified form, usually called oleoresins, oily extracts or crude extracts. In order to achieve a higher pigmenting capacity, the xanthophyll containing extracts are further treated to hydrolyze the esterified xanthophylls, generally by means of saponification processes.
In order to obtain the free form of such pigments, there is a variety of processes to hydrolyze xanthophylls, such as the process described in U.S. Pat. No. 3,783,099, granted on Jan. 1, 1974, in which the plant material containing xanthophylls is mixed with an enzyme such as cellulase, protease, etc. and a chelating agent such as ethylenediamine tetra-acetic acid (EDTA), which achieves the hydrolysis of the esters at constant pH conditions and carries away the xanthophylls in their free form, thus avoiding a further saponification step.
At industrial scale, the most common hydrolysis process used, as mentioned above, is the saponification or alkali treatment of plant extracts. The state of the art acknowledges a variety of saponification processes of esterified xanthophylls from plant extracts.
U.S. Pat. No. 3,523,138, granted on Aug. 4, 1970, describes several processes for treating marigold flower extracts by means of aqueous solutions of alkali metal hydroxides in the presence of low molecular weight alkyl alcohols, in which temperatures ranging from 0 to 150° C. can be used with reaction times of between 1 minute and 8 hours, depending on the temperature employed, since the reaction time is reduced when the temperature is increased. This patent states that, in order to obtain an optimum result at 90° C., the process should take 3 hours.
Mexican Certificate of Invention No. 1697, granted on May 4, 1978, describes a process for obtaining a powdered pigmenting concentrate with enhanced activity, starting from oleoresins containing xanthophylls, in which the xanthophylls contained in marigold flowers are extracted using solvents such as chloroform, hexane or acetone, that are removed in a later stage, thus obtaining a pasty mass containing xanthophylls, fats, resins and waxes, which were carried away by the solvent. Once xanthophylls are extracted, an emulsion is formed by means of a surfactant, for instance a detergent, in order to assist in the incorporation of the pasty mass in aqueous alkali solutions, such as ammonium hydroxide, potassium hydroxide or sodium hydroxide, in order to carry out saponification at a temperature of from 50 to 90° C. during a period of time of from 15 to 60 minutes, after which an antioxidant and a xanthophyll fixer such as lecithin, as well as a substance that adheres to xanthophylls such as carboxymethyl cellulose, gelatin or palmitates are added. The solution obtained is then neutralized using a precipitating agent such as phosphoric acid, silicic acid or magnesium chloride, in order to neutralize and carry away the xanthophylls. Finally, the precipitate formed is filtered, washed, dried and ground in order to obtain the final powdered pigment.
In the prior art discussed in the above referred to Certificate of Invention, it is established that until that moment, no process for the obtention of powdered pigmenting concentrates starting from xanthophyll oleoresins in order to enhance their activity, had ever been conceived.
Mexican Certificate of Invention No. 6010, granted on Sep. 24, 1984, describes a process for obtaining a stable xanthophyll pigmenting concentrate from marigold flower, comprising the steps of extracting oil from marigold flowers using a solvent; saponifying the oily extract-solvent mixture with an alkali at a temperature of from 55 to 65° C. at atmospheric pressure; removing the solvent for obtaining a xanthophyll-rich concentrate, and stabilizing the concentrate by means of the addition of an antioxidant selected from ethoxyquin and ascorbic acid.
In the prior art discussed in Certificate of Invention No. 6010, several documents are cited, including the Mexican Certificate of Invention No. 1697. In these documents, it is possible to ascertain the research and development carried out from the year 1915 in the field of xanthophylls, as well as in

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