MXPA98004719A - A process for the formation, isolation and purification of the edible crystals of xantofila of the plan - Google Patents

Abstract

The present invention relates to a process for the formation, isolation and purification of xanthophyll crystals, preferably the lutein of dead flower petals, zeaxanthin of wolfberries or capsanthin and capsorubin of red peppers. An extract of the diester-containing plant of xanthophyll is saponified in a propylene glycol and aqueous alkali composition to form the xanthophyll crystals. Crystallization is achieved without the use of added organic solvents. The crystals are isolated and purified. Substantially asymptomatic xanthophyll crystals are suitable for human consumption and can be used as a nutritional supplement and as an additive in food.

Description

A PROCESS FOR THE FORMATION, ISOLATION AND PURIFICATION OF EDIBLE CRYSTALS OF XANTOFILA OF PLANTS Description Technical Field The present invention relates to a process for the formation, isolation and purification of carotenoid compounds and more particularly to a process for the formation, isolation and purification of plant xanthophyll compounds in a crystalline form suitable for human consumption.

Background of the Invention Carotenoids include hydrocarbons (carotenes) and their oxygenated, alcoholic derivatives (xanthophylls.) .. Representative examples of carotenoids include carotene-beta, carotene-alpha and lycopene.Examples of xanthophylls include lutein, zeaxanthin, capsorubin, capsantil. , astaxanthin and canthaxanthin.

Carotenoids are abundant in fruits and vegetables and have been studied extensively as antioxidants for the prevention of cancer and other human diseases. Among dietary carotenoids, the focus has been on carotene-beta which has been established by playing an important role in the prevention of various types of cancer. * 10 The latest research shows that other carotenoids, particularly xanthophylls, have strong abilities as antioxidants and may be useful in the prevention of diseases, including cancer.

For example, it was reported that consumption of lntein and zeaxanti leads to a 40 percent reduction in age-related muscle degeneration (Seddon et al., 1994, J. Mer. Med. Assoc. 272 (18): 1413-1420). It was also reported that an increased level decarotages of serum other than carotene-beta are associated with the lower incidence of heart disease (Morris et al., 1994, J. Amer. Med. Assoc. 272 (18): 1439-1441). The xanthophyll, due to its yellow to red color and of natural occurrence in food humans, also finds its use as food coloring. Thus, there is an increased need for substantially pure xanthophylls, which can be used as nutritional supplements and food additives. 5 Although it is present in many plant tissues, carotenoids that do not contain pigments from other plants are those that are most easily obtained from flowers (dead flower), fruits (berries) and root tissues (carrots and ~? 10 yellow potatoes). The hydrocarbon carotenes typically occur in uncombined form without bodies of oplosthus within the cells of the plant. Xanthophylls typically occur in plant chromplats, such as long-chain fatty esters, typically diesters. of acids such as palmitic and myristic acids. Although the chemical processes for the synthesis of the xanthophyll starting materials commercially The available ones are known, these processes are extremely time consuming, involve multiple steps and have not provided an economic process in the production of xanthophylls. A more economical route for the large-scale production of substantially pure xanthophylls is a process that extracts, assulates and purifies the cantofilas from natural sources. However, previous methods that "asylate the xanthophylls of plants use a quantity of organic solvents.

The previous investigators also used a commercially available saponified dead flower olioresin, which does not contain lutein, as starting material, and then added the appropriate solvents to crystallize the saponified oleoresin lutein (Tcyczko ski and Hamilton, Poultry Sci. 70 (3); 651-654, 1991; Patenre of the U.S. No. 5,382,714). The preparation of purified lutein dike acid esters is also described in US Pat. No. 4,048,203.

Methods for obtaining cordate leaves are described in H. Strain, Leaf Xanthopylls, Carnegie Institution, < ^ Washington, D.C. (1936). Among the techniques described, including those to obtain free-forming xanthofilas in the leaves, Strain describes the obtaining of xanthophylls free of xanthophyll diesters present in the pods (calix) of Physalis alkekengi.

In that last preparation, on pages 99-104, the almost dry pods were cut into small sections with a grinder of meat and the pieces extracted with petroleum ether. The extract was concentrated in a small volume and the xantopila esters present were saponified with alcoholic potassium salt. Alcohol was not named, but it is assumed to be methanol from the subsequent test. Water 5 was added to the alcohol solution to precipitate xanthophyll. The precipitated xanthophylls were then crystallized several times from chloroform and an eluent such as methanol or petroleum ether, and then pyridine.

The procedure previously described by Strain has several disadvantages in the production of an edible xanthophyll. First, the hydrophobic petroleum ether used to extract xanthophyll dies is not extracted before sanponification and can be entrapped in xanthophyll hydrophobic precipitate. Second, the use of monohydric alcohol such as methane or even ethane can cause * formation of ethyl or methyl esters of fatty acids not soluble in water that can also be trapped with hydrophobic xanthophylls. This entrapment could be the reason why so many steps of recrystallization are required. Very cold temperatures such as -12 ° C and -70 ° C were also required during those recrystallizations.

The disadvantage of these methods is that xanthophylls can retain some of the solvent (s) from which they are isolated and purified. In addition, these methods require the washing of * xanthophylls with more solvents. The solvents can usually be extracted by drying the crystals at elevated temperatures. But in some cases, it is difficult or impossible to extract the solvent. Traces of toxic organic solvents in the purified, isolated xanthophyll product make it unsuitable for human consumption. Another disadvantage of using a process that uses organic solvents is that these solvents are difficult to handle and present physical and chemical hazards. Yet another disadvantage of that use is that organic solvents are a waste of danger and present a problem for their disposal.

There is therefore a need for an economical means of producing a substantially pure, edible xanthophyll such as lutein or zeaxanthin where the use of hazardous or toxic organic solvents is not employed.

This process is disclosed herein after it provides an edible xanthophyll. 20 Brief Compendium of the Invention The present invention relates to a process for the extraction, isolation and purification of xanthophylls, preferably lutein or zeaxanthin, from an extract * of the plant that contains xanthophyll diester. Preferred plants are those known to contain high concentrations of the desired xanthophyll diester such as lutein in the flowers of the dead (Tagetes sp., Such as Tagetes erecta), zeaxanthin in the olfberry (a Lycium sp., Such as Lycium barbarum) or capsanthin and capsorubin in the pepper plant (a Capsicum sp., such as Capsium annum). The process contemplates the use of plant extract grade of food containing xanthophyll diester (oleoresin) that has no organic solvent; that is, oleoresin contains less than 1 percent organic solvent. The extract is mixed with a composition containing propylene glycol and an aqueous lcali, preferably potassium hydroxide for form a reaction mixture of which the oleoresin and the propylene glycol together constitute at least 75 percent by weight. The reaction mixture formed in this way is maintained at a temperature of about 65 ° C to about 801 ° C for a period of Time (typically at least 3 hours) sufficient to saponify the xanthophyll diester and form a saponified reaction mixture containing free xanthophyll in the form of crystals. The saponified extract is mixed with a dilution amount of water to dissolve the impurities soluble in water and reduce the viscosity of the reaction mixture. The diluted mixture is mixed gently until homogeneous and then filtered to collect the xanthophyll crystals. The collected xanthophyll crystals are washed with warm water and dried. No organic solvent other than propylene glycol is used in the isolation and purification of the xanthophyll of the oleoresin containing xanthophyll diester.

The present invention has several advantages. An advantage of this invention is that it provides a process for the production of a substantially pure xanthophyll that is suitable for human consumption without the use of relatively toxic organic solvents during isolation or crystallization. Another advantage of this invention is that it provides a process for the production of a substantially pure, edible xanthophyll, without the need for recrystallization. Yet another advantage of this invention is that it provides a process for the production of a xanthophyll substantially pure, edible, which is economical and easy to carry out on a large commercial scale. Additional advantages will be apparent to those skilled in the art from the description that follows.

Detailed Description of the Invention * According to the present invention, a xanthophyll, preferably lutein, zeaxanthin or capsanthin and capsorubin is formed, isolated and purified from the material of the plant containing xanthophyll diester, preferably a plant known to have high concentrations of dester. desired of xanthophyll. The flowers of the dead (Tagetes erecta) are an excellent source of lutein because they contain one of the highest known concentrations of lutein diester in nature, while the fruit of olfberry (Lycium barbarum) is an excellent source of zeacanthine because it contains high concentrations of zeaxanthin diesters, and the pepper plant (Capsicum annum) it's a good one source of capsanthin and capsorubin for the high concentrations that have of capsanthin and dextrose of capsorubin. Other plants that are known to have high concentrations of the desired xanthophyll can also be used. A source of the contemplated plant contains xanthophyll in the esterified form as the fatty acid of a long chain of mono or di-C12-C18, such as luric, myristic acids. oleic, linoleic and palmitic. Lutein in dead flowers, zeaxanthin in olfberries and capsanthin % and capsorubin in pepper plants are present as xanthophyll diesters. Free or non-esterified xanthophyll can be found in other plants such as spinach, broccoli, kale and corn.

The xanthophyll esters are extracted from the plant, preferably from the flower, fruit or root, with an appropriate organic solvent or a mixture of solvents that can be easily extracted from the extract. The use of flowers, roots and fruits is a source of the desired xanthophyll that avoids the difficulty in separating xanthophyll from other pigments such as chlorophyll.

In one embodiment of the invention, the dead flowers (Tagetes erecta) dried and ground that are commercially available are used as a source of lutein. In another modality, wolfberry fruits (Lycium barbarum) are used as a source of zeacanthine, while red peppers (Capsicum annu) are a source of capsanthin and capsorutin.

The organic solvents that have been used to extract carotenoids from plants include methanol, acetone, Ethyl acetate, diethyl ether, petroleum ether, hexanes, heptanes, chloroform and tetrahydrofuran. In a modality * Illustrative of the invention, the lutein diester is extracted from the dead flowers dried with hexane. In another illustrative embodiment, the zeaxanthin diester is extracted from dried wolfberries with ethyl acetate and hexane. The extraction is carried out according to the processes known in the art. Solvents are removed, resulting in an extract that contains a high level of xanthophyll ester and is approximately 99 percent and preferably approximately 99.9 percent free of the extract of the organic solvent; that is, it contains less than 1 percent and preferably less than about 0.1 of the organic solvent by weight. The extract that is free of solvent is referred to in the technique as an oleoresin.

The exemplary toxicities of propylene glycol and the different solvents previously used for the recovery of xanthophyll crystal are available from various sources. The comparative oral toxicities in the rat of The Merk Index, lia. Edition, Merck & Co., Inc. Rahway, MJ (1989) are given in the following Table as LD50 values.

Report of Rat Toxicities Solvent LD50 (ml / Kg) Propylene glycol 25 5 Ethyl acetate 11. 3 Ethyl alcohol 10. 6 - 7. , 6 Chloroform 2. 18 Pyridine 1. 58 In the present invention, the oleoresin that is formed in this way is purified by mixing with the propylene glycol (1,2-propanediol) and an aqueous alkali, preferably potassium hydroxide. It was surprisingly discovered that the free xanthophylia formed in the saponified oleoresins containing propylene glycol were present as crystals. The crystals were clearly seen under a microscope. In this way the crystallization of xanthophyll was achieved directly via the saponification reaction and by the addition of several organic solvents as previously had been done. Also, unlike previous methods - they used the saponified dead flower oleoresin as a starting material to isolate lutein (Tcyczkowski and Hamilton, Poultry Sci. 70 (3): 651-654, 1991; United States No. 5,382,714), there was no need to crystallize the lutein from the oleoresin of the saponified dead flower by the addition of organic solvents.

The large size of the crystal is important to obtain the xantofilia to a desired purity. To obtain the desired large crystals (average size from about 0.01 to about 0.1 mm) the concentrations of the four constituents of the saponification reaction mixture are preferably present in the About 35 to about 50 percent by weight of oleoresin to about 30 to about 45 percent by weight of propylene glycol of about 5 to about 10 percent by weight of water-soluble alkali as a hydroxide of potassium from about 7 to about 15 percent by weight of water, as the mixed components initially, that is, the components before the reaction. The oleoresin and the propylene glycol together form at least about 75 percent of the weight of the saponification reaction mixture. Most preferred, those proportions by weight can be expressed simply as being approximately 4: 4: 1: 1, in the order recited. In a particularly preferred embodiment, those weights are 41 percent oleoresin, 41 percent propylene glycol, and 18 percent aqueous potassium hydroxide (55 percent water). These proportions may vary depending on the material of the plant used.

In addition, the saponification reaction preferably proceeds slowly. In an exemplary embodiment, about 1000 Kg of dead flower extract is mixed with the propylene glycol, which finely dissolves or disperses the extract. The mixture is heated to a temperature range ~10 of about 50 ° to about 60 ° C, preferably about 55 ° C, to obtain a homogeneous liquid having a viscosity similar to that of engine oil at room temperature. A solution of potassium hydroxide is added slowly and evenly to the extract Dissolved / dispersed (oleoresin) for a period of time to form the saponification reaction mixture. When at least 10 minutes, but preferably 30 minutes are used for the formation of the saponification reaction mixture with the above amounts of the components, and the mixture is maintained with gentle agitation for a sufficient period of time to saponify the present xanthophyll dieters, at least 3 hours, but preferably 10 hours.

When the alkali solution is initially added to the * oleoresin, the temperature rises to about 70 ° C and the additional heat is added to maintain the temperature at about 65 ° C to about 80 ° C, and preferably about 70 ° C throughout the reaction, * that is, until saponification of the xanthophyll diester is complete. The termination of the saponification can be easily determined by a thin layer of chromatography (TLC) which will be presented hereinafter. w * 10 Sodium hydroxide can also be used for saponification, but potassium soaps are more desirable because they are generally more soluble in aqueous solutions than in sodium soaps. The alkali 15 which is used in the preferred embodiment of the invention is aqueous caustic potassium salt which is 45 weight percent potassium hydroxide.

The saponification reaction penetrates the fatty acids 20 of the xanthophyll diester, producing free xanthophyll in the form of crystals, as well as the potassium and sodium soaps of fatty acids. It is possible that the mono-fatty acid esters of propylene glycol are formed during saponification. If they are present, those materials do not interfere with the crystallisation of xanthoglyl, and this is possibly due to their greater solubility in water compared to the mono-elite or mono-methyl esters of those fatty acids.

The mixture of the saponification reaction is then diluted - mixing with a water of low ionic strength (deionized), preferably warm, for example, of about 60 ° -80 ° C, in order to further reduce the viscosity of the reaction mixture and dissolve the water-soluble impurities. If the cold water is used, additional heat is provided to the diluted reaction mixture to maintain a temperature range from about 60 ° C to about 80 ° C, preferably about 70 ° C. 15 If the temperature is too cold, the diluted reaction mixture is too viscous to filter. If the temperature is too hot, the diluted reaction mixture foams and interferes with the crystal recovery.

Sufficient water is added to form a diluted reaction mixture containing about 5 to about percent volume of the reaction mixture of saponification. With this, about 3 to about 19 volumes of dilution water are added per volume of reaction mixture. for a preferred embodiment, the ratio is about 10 volume percent of the saponification reaction mixture to about 90 volume percent of the dilution water.

The diluted reaction mixture that is formed by the addition of water is gently agitated until it is homogeneous and then either it is imbedded or otherwise fed into a filtering device that collects the crystals. Any filtration device known in the art can be used. In a preferred embodiment of the invention, the mixture is fed to a centrifugal filter / basket having a maximum pore size of 35-40 μm.

Most of the chemical impurities in the extract are extracted during the filtration step because the soluble nature of the fatty acid soaps themselves and their solubilizing power in a largely aqueous composition, and the soluble nature of the xanthophyll crystals in the that same aqueous composition. Other water-soluble impurities such as anthocyanins and water-soluble flavonoids are also extracted.

After filtration, the collected crystals are washed extensively with a low ionic strength (deionized) water at a temperature in the range of about 70 ° C to about 90 ° C, preferably about 85 ° C. At the warm temperature used, water removes most residual chemical contaminants that may be present, such as potassium or hydroxide. sodium, soaps of residual potassium and the propylene glycol used in the saponification reaction. The washed crystals are dried by suitable methods, such as freeze drying, rotary vacuum drying or purging with heated nitrogen. 15 Based on visible / UV spectrophotometry, the resulting crystals obtained by this process contain approximately 70 to 85 percent of the total carotenoids, and are substantially pure or estimated xanthophylls. In an embodiment of the invention in which lutein is isolated from the dead flower extract, carotenoids, as determined by quantitative HPLC analysis, consist of 85 to 95 percent lutein of all trans, 0.2 to 1.5 percent of its geometric 5 isomers, 2.5 to 8.0 percent of all trans zeaxanthins, less than 1.0 percent of alpha and beta cryptoxanthin, and traces of other crotenoids such as neoxanthin and violaxanthin. The presence of low levels of these other carotenoids are of dietary origin and are routinely found in much higher concentrations relative to that of lutein in human serum or plasma.

The lutein crystals contain approximately 0.5 to 5.0 percent water and may contain traces of fatty acid soaps and / or fatty acids not completely washed from the crystals. However, the substantially pure xanthophylls that are obtained by this process do not contain residues of toxic organic solvents, (ie, solvents other than propylene glycol) or other toxic compounds and are suitable for human consumption.

The dried xanthophyll crystals thus formed are typically mixed with an edible triglyceride oil for use in food or as a cosmetic dye. The xanthophyll content of the mixture is typically from about 0.1 to about 35 percent by weight. Examples of edible oils include candelilla oil, coconut oil, cod oil, cottonseed oil, olive oil, palm oil, corn oil, soybean oil, peanut oil, poppy seed, sunflower oil and safflower oil. The use of an oil having a relatively high concentration of unsaturated fatty acids is preferred; that is, the use of an oil having an iodine value is preferred. of about 100-150. the mixing is typically carried out using a high shear mixing apparatus, as is well known. Co-solvents and additives such as ethane and alpha tocopheron, respectively, may also be present as noted in the U.S. Patent. No. 5,382,714.

The following examples are offered to illustrate, but do not limit the present invention.

Best Way to Carry Out the Invention Example 1: Isolation of the lutein from the petals of the dead flower. Extraction 0 Approximately 1000 Kg. Of commercially available milled and dried dead flower petals are agglomerated and extracted with 40,000 liters of warm hexane (approximately 60 ° C). The agglomerate was submerged for 1 hour and drained.

This process was repeated 8 to 10 times to ensure complete extraction of the pigments present in the flowers. The hexane extracts were combined and the hexane was evaporated using vacuum and heat. After the hexane was extracted, approximately 100 Kg of an oily extract (oleoresin) remained.

Saponification / crystallization reaction % 10 The oleoresin from the flower of death (11140 Ibs - 40.9 percent) was mixed by stirring it with 1, 2-propanedium (1140 pounds-40.9 percent) and heating to 551C to form a homogeneous stirrable liquid. The aqueous caustic potassium salt containing 45 percent by weight of hydroxide of Potassium (540 pounds - 18.2 percent) was added slowly and evenly over a period of 30 minutes. The reaction temperature rose to 70 ° C and was maintained at 70 ° C for 10 hours with gentle agitation. The lutein crystals appeared within this reaction mixture of saponification during this period of time.

Collection of lutein crystals A portion of the saponified oleoresin (saponification reaction mixture: 233 pounds) produced from the above reaction was diluted to 10 percent with deionized water. This mixture was heated to 70 ° C, stirred until homogeneous, and fed into a 30-inch TOLHURST ™ spin (available from Keteme Process 5 Equipment, Santee, CA., equipped with a maximum pore size filter). 35-40 μm The crystals harvested from lutein were washed with deionized water (560 pounds) at 85 ° C by spraying warm water through the nozzles of the wet rayon impeller, after washing the wet crystals (28 pounds) were spread on stainless steel trays and placed in a VTRTIS ™ freeze dryer (available from Virtis Co., Gardiner, NY, and dried using the following drying conditions: freeze -40 ° C at 100 m vacuum of submerged torr, supply thermal to the trays of 20 ° C and a duration of 48 hours. The analysis of the crystals gave the following results: dry crystal weight 3.63 kg. 20 total carotenoid level 79.0% (visible / UV spectrophotometry) lutein (adjusted HPLC *) 73.6% moisture level (water) 1.28% * 93.1 percent of the total carotenoid analyzed as whole trans lutein.

The recovery of carotenoids was 59 percent 5 of the total of carotenoids present in the starting oleoresin. The dried crystals were stirred with safflower oil using - a high mixer of constant effort. The final product of lutein in safflower oil contained 20 percent lutein of all trans. * 10 Isolation and collection of capsanthin and capsorubin crystals Similar manipulations using an oeloresin of dried red peppers of Capsicum annum in place of the oleoresin of ground dead flower petals provide a mixture of capsanthin and capsorubin crystals.

Example 2: Isolation of the lutein from the petals of the flower of the dead This study was carried out using the same method of Exemplary, except that the reaction mixture contained 50.2 by percent weight of the dead flower oleoresin (1401 pounds) that was mixed with 30.4 percent by weight of 1,2-W propanediol (848 pounds) and 19.4 percent by weight of the aqueous potassium hydroxide (45 percent). KOH: 542 pounds).

The saponified oleoresin (462 pounds) produced from the above reaction was also diluted to 20.4 volume percent with deionized water and this mixture was diluted food in a 16 inch TOLHURST ™ centrifuge. ^ p ~ - 10 equipped with a filter of maximum pore size of 25-30 μm and filtered. Analysis of the crystals showed a lower total carotenoid level, 64.7 percent than in Example 1.

Example 3: Extraction, isolation and purification of zeaxanthin from wolfberries (Lycium barbarura) extraction Seventy-five grams (75 gr.) Of berries were hydrated and homogenized with 200 gr. of water. The seeds were removed by filtration. The resulting material was centrifuged to form a lump containing carotenoids. The excess water was removed from the pod. The lump was spread and dried using heat and air. The dried material was finely milled and analyzed for the total caratenoid content and found to contain 6.46 g / kg.

A small portion of this material, 6 grams, was extracted with ethyl acetate of hexane using 100 ml of each solvent with each 2 grams of dried fruit crumb. These extractions were conducted at 50 ° C for several hours. The extracts were combined and filtered and then evaporated under reduced pressure with apparent drying to form an oleoresin free of organic solvent for saponification.

Saponification / crystallization Approximately 1 gr. of dried oleoresin was suspended in 1 gr. of propylene glycol. 0.5 g was added to this mixture. of 45 weight of aqueous potassium hydroxide. This mixture was mixed with a small magnetic stir bar and heated to approximately 70 ° C on a hot plate. The aliquots were taken during the reaction and subjected to TLC analysis using a silica gel and a 3: 1 by volume mixture of hexane and acetone as the eluting solvent for an equitable measure of the degree of saponification and microscopic observations. TLC indicated a high degree of saponification after 3 hours.

The microscopic observations showed the formation of the crystal structures of seaxanthin during the course of the reaction.

The above description and examples tend to be illustrative and not limiting. Still other variations are possible within the spirit and scope of this invention and will readily be presented to those skilled in the art. 10 fifteen 0

Claims (8)

1. A process for the production of the xanthophyll crystals from an oleoresin of the plant containing xanthophyll diester comprising the steps of: (a) mixing the oleoresin with the propylene glycol with heating at a temperature of about 50 ° C to approximately 60 ° C to form a homogeneous liquid; (B) mixing an aqueous alkaline solution of sodium or potassium hydroxide with the homogeneous liquid to form a saponification reaction mixture consisting essentially of about 35 to about 50 weight percent oleoresin; about 30 to about 45 weight percent propylene glycol; about 5 to about 10 percent by weight of alkali as potassium hydroxide and about 7 to about 15 percent by weight of water as the components ^ mixed initially, where the total weight of the oleoresin plus the propylene glycol make up at least 75 percent by weight of the mixture 5 reaction; (c) maintaining the saponification reaction mixture at a temperature of about 65 ° C to about 80 ° C for a sufficient period of time to saponify the xantopfila diester Jk 10 and forming a saponified reaction mixture containing xanthophyll crystals; (d) mixing about 3 to about 19 volumes of water at a temperature of about 60 ° C to about 80 ° C. 15 volume of the saponified reaction mixture to form a diluted reaction mixture that TE. Contained xanthophyll crystals; W (e) Gently mix the diluted reaction mixture until it is homogeneous; 20 (f) collecting the xanthophyll crystals from the diluted reaction mixture, and; (g) washing and then drying the harvested xanthophyll crystals.

2. The process of claim 1, wherein the extract of the plant is dead flowers (Tagetes sp.) And xanthophyll is lutein.

3. The process of claim 1, wherein the extract of the plant is from the wolfberry fruit (Lycium sp.) And the xanthophyll is zeaxanthin. -.

4. The process of claim 1, wherein the ratio of the oleoresin to the co-alkali alcohol, with water is about 4: 4: 1: 1, in recited order.

5. The process of claim 1, wherein the alkali is a potassium hydroxide.

6. The process of claim 1, wherein the saponification reaction mixture is maintained for a period of time of at least 3 hours.

7. The process of claim 1, wherein the ratio of the saponified reaction mixture to water is 1: by volume.

8. The process according to claim 1 including the additional step of mixing the dried xanthophyll crystals with an edible triglyceride oil to form a mixture containing about 0.1 to about 35 weight percent xanthophyll.