Method for Preparing High-Content Food-Grade Zeaxanthin

Abstract
This invention has disclosed a method for preparation of food-grade zeaxanthin through chemical isomerizaton reaction from lutein. The technical issues to be solved in this invention are quite low product yield obtained with existing methods, need of purification treatment process, and inadaptability to industrialized production. The technical schemes of this invention are: a. Mix xanthophyll crystal or its fatty acid ester with food-grade glycol or propylene glycol, for full dissolution under 60-90° C. temperature. Add organic alkali into the mixed liquor acquired from step 1, for isomerization reaction to take place under inertial environment. c. Dilute the reaction solution gained from step b with the mixed solution of deionized water and ethanol, and separate the obtained crystal with conventional separating method. d. Vacuum dries the acquired crystal from step c, to get the zeaxanthin crystal. Glycol or propylene glycol is used in this invention for isomerization reaction under inertial environment after it has fully dissolved raw material under proper temperature. The product yield is reachable to more than 60%, very adaptable to industrialized product, without the need for further purification treatment.
Description
DETAIL DESCRIPTION OF THE INVENTION
Example 1

Weigh 30 g xanthophyll crystal from saponification of marigold oleoresin (wherein the total carotenoid is 88.5% and the proportions of lutein and zeaxanthin account for 92% and 7% of total carotenoid, respectively, the rest being a few other carotenoids). Mix with 540 ml glycol and stir and dissolve for 1.0 hr under 80° C. Heat up the mixture to 90° C. after dissolution is completed, and instill 40 g 6.85 mol/L sodium methoxide solution, and addition of alkali catalyst is to be completed within 45 min. Reaction is to take place at this temperature, and the lutein and zeaxanthin in the reaction solution are to be sampled at an interval of 0.5 hr after reaction for 4.0 hr and analyzed with high performance liquid chromatographic method for their proportions, to get a measurement of 89.7% proportion of zeaxanthin of total carotenoid in the reaction liquid after 8.5 hr. Drop the temperature of reaction mixture to 70° C., and add a mixture composed of 100 ml deionized water and 600 ml food-grade ethanol under the stirring condition to dilute the reaction substance. While separating crystals from the diluent mixed solution with centrifugal method, a mixture of water and ethanol is used for spraying rinse, until the washed out liquid is nearly colorless. 21.3 g tangerine colored crystal can be obtained for the final filtrated matter through vacuum drying. Analyzed by ultraviolet visible light spectrophotometric method, the total carotenoid content in this crystal is 85.7%. The yield of total carotenoid is 68.6%. Analyzed with high performance liquid chromatographic method, the zeaxanthin wherein account for 91.2% of total carotenoid and the lutein occupies 6.1% of total carotenoid.


No toxic organic solvent is contained in the products, suitable to be used in the forms of nutrition extender and food additive. The application form of this crystal can be oil suspension (mixed and emulsified with plant oil), granule beads (microcapsule condensed through spray condensation granule beads technology), and dry powder (microcapsule through spray-drying), etc.


Operating conditions and product characters in this example are listed in Table 1.


Example 2

Weigh 40 g xanthophyll fatty acid ester refined from marigold oleoresin (wherein the carotenoid fatty acid ester content of total carotenoid is 72.5%, and the proportions of lutein and zeaxanthin in total carotenoid are 91.6% and 6.8%, respectively, the rest being a few other carotenoids). Fully mix xanthophyll fatty acid ester with 470 ml propylene glycol and dissolve the mixture under 70° C. Heat up to 85° C. after dissolution is completed. Add 110 g 2.92 mol/L sodium tertiary butyl alcohol solution drop by drop, and it is determined after reaction standing for 14.5 hr with high performance liquid chromatographic method that zeaxanthin wherein accounts for an 84.6% proportion of the total carotenoid. Cool down to 70° C. and add a mixed liquid composed of 1000 ml deionized water and 600 ml food-grade ethanol to dilute the reaction liquor. Extract and filter out the crystals from separation, with a mixture of water and ethanol for washing during the extracting and filtering process, until the washed out liquid is nearly colorless. 10.3 g saffron colored crystal is gained from the filtrated insoluble substance after vacuum drying. Analyzed with ultraviolet visible light spectrophotometric method, the total carotenoid content in the crystal is 81.3%, while the yield of total carotenoid is 54.0%. Through HPLC analysis, zeaxanthin in the product accounts for 85.2% of the total carotenoid, and the lutein occupies 11.3% of the total carotenoid, both in dissociative forms.


Operating conditions and product characters in this Example are listed in Table 1.


Examples 3-4

Implementation processes for Examples 3-4 are similar to those of Examples 1-2, and the analytical results for their main technical parameters and some product characters are listed in Table 1.









TABLE 1







Analysis of Main Technical Parameters and Some Product Characters in


Examples 1-4











Item
Example 1
Example 2
Example 3
Example 4





Type of Raw Materials
Xanthophyll Crystal
Xanthophyll Fatty
Xanthophyll Crystal
Xanthophyll Fatty




Acid Ester

Acid Ester


Quantity of Raw Material
30 g
40 g
30 g
40 g


Type of Solvent
Glycol
Propylene Glycol
Propylene Glycol
Glycol + Propylene






Glycol (1:1)


Quantity of Solvent
540 ml
470 ml
450 ml
400 ml


Type of Catalyst
6.85 mol/L
2.92 mol/L
1.96 mol/L
5.15 mol/L



Sodium Methoxide
Sodium Tertiary
Sodium Dimethyl
Sodium Ethoxide



Solution
Butyl Alcohol
Sulfoxide Solution
Solution




Solution


Quantity of Catalyst
40 g
110 g
150 g
83 g


Reaction Temperature
90° C.
85° C.
80° C.
90° C.


Reaction Duration
8.5 hr
14.5 hr
6.0 hr
12.0 hr


Separating Method
Centrifugal
Extraction and
Extraction and
Centrifugal




Filtration
Filtration


Quantity of Product
21.3 g
10.3 g
17.3 g
9.7 g


Total Carotenoid Content
85.7%
81.3%
88.4%
83.5%


in Product


Proportion of Zeaxanthin
91.2%
85.2%
92.3%
91.8%


of Total Carotenoid


Proportion of Lutein of
6.1%
11.3%
6.1%
7.0%


Total Carotenoid


Yield of Total Carotenoid
68.8%
54.0%
57.6%
51.7%








Claims
  • 1. A method for preparing high-content food-grade zeaxanthin comprising following steps: a. mixing crystals of xanthophyll or its fatty acid ester with food-grade glycol or propylene glycol under 60-90° C. temperature until the crystals of xanthophyll or its fatty acid ester are full dissolved;b. dripping organic strong base solution into the mixed liquor gained from step a then put them in inertial environment to take isomerization reaction;c. diluting the reaction solution acquired from step b with a mixture of deionized water and ethanol, then separating obtained crystals by conventional separation method;d. vacuum dry the crystals gained from step c, to get crystals of zeaxanthin.
  • 2. The method for preparing high-content food-grade zeaxanthin according to claim 1, wherein the temperature for the isomerization reaction is 60-120° C.
  • 3. The method for preparing high-content food-grade zeaxanthin according to claim 1, wherein the temperature for the isomerization reaction is 80-95° C.
  • 4. The method for preparing high-content food-grade zeaxanthin according to claim 3, wherein the temperature for dissolution of crystal of xanthophyll or its fatty acid ester and food-grade alcohols is 70-80° C.
  • 5. The method for preparing high-content food-grade zeaxanthin according to claim 4, wherein the organic strong base is sodium methoxide, sodium ethoxide, sodium tertiary butyl alcohol, sodium dimethyl sulfoxide, potassium methoxide, or potassium ethoxide, molar weight of the organic strong base is 1-15 times of the molar weight of the crystals of xanthophyll or its fatty acid ester.
  • 6. The method for preparing high-content food-grade zeaxanthin according to claim 5, wherein the molar weight of the organic strong base is 4-10 times that of the crystals of the xanthophyll or its fatty acid ester.
  • 7. The method for preparing high-content food-grade zeaxanthin according to claim 6, wherein the glycol or propylene glycol as a volume 2-40 times that of the crystals of xanthophyll or its fatty acid ester.
  • 8. The method for preparing high-content food-grade zeaxanthin according to claim 7, wherein the glycol or propylene glycol as a volume 5-20 times that of the crystals of xanthophyll or its fatty acid ester.
  • 9. The method for preparing high-content food-grade zeaxanthin according to claim 8, wherein the xanthophyll fatty acid ester or xanthophyll crystal is derived from marigold, the former being refined from oleoresin of marigold containing more than 60% of total carotenoid ester content, and the latter is the crystal derived from oleoresin of marigold through saponification treatment.
Priority Claims (1)
Number Date Country Kind
200610053642.3 Sep 2006 CN national