CN101891664A - Method for purifying lutein esters - Google Patents
Method for purifying lutein esters Download PDFInfo
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- CN101891664A CN101891664A CN201010232719XA CN201010232719A CN101891664A CN 101891664 A CN101891664 A CN 101891664A CN 201010232719X A CN201010232719X A CN 201010232719XA CN 201010232719 A CN201010232719 A CN 201010232719A CN 101891664 A CN101891664 A CN 101891664A
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Abstract
The invention discloses a method for purifying lutein esters and in particular relates to a method for extracting high-purity lutein esters from marigold ointment. The method is characterized by dissolving the marigold ointment into ethyl acetate at 25-80 DEG C and stirring the mixture for 1-6h; adding absolute ethyl alcohol to the liquid obtained through heat filtration and stirring the mixture at 20-70 DEG C for 0.5-5.0h to form uniform solution and then filtering the solution after cooling the solution at minus 5-30 DEG C for 5-20h; and then washing filter cakes with lower alcohol and drying the solid under vacuum to remove the solvent residues, thus obtaining the required high-purity lutein esters. The content of the lutein esters is 70-80%. The method is high in product yield, simple and convenient to operate and easy to realize large-scale industrial production.
Description
Technical field
The present invention relates to a kind of method of purifying lutein esters, in particular, the present invention relates to a kind of method of from the Flower of Aztec Marigold ointment, extracting the high purity lutein ester.
Background technology
Up to now, having many is the relevant report that raw material extracts lutein ester with the marigold oil resin.For example, US4,048,203 dissolving marigold oil resins are settled out lutein ester by cooling solution with containing the hot alkanol that is no more than 4 carbon atoms, remove by filter vacuum-drying again behind the alkanol, but the lutein ester content that this method obtains has only 51%, does not reach the high-content requirement.US6 by with varsol lixiviate marigold flower, obtains medicinal extract with alcohol precipitation in 191,293 again, but the purity of the lutein ester that obtains with this method changes greatly because of the difference of raw materials quality, is difficult to control in suitability for industrialized production.CN1,120, the Flower of Aztec Marigold of handling with Petroleum ether extraction among the 565A obtains partly-hydrolysed oleo-resinous, and its purity has only about 12.0%, and yield is low.
CN1432567A has disclosed the first acetone extraction lutein oleoresin of using, again with the concentrated mother liquor of crystallization acetone such as butanols or Virahol, thereby obtain the higher fatty acid ester of lutein enriched material of content, but yield is not high on the one hand for this method, on the other hand owing to use the higher butanols of boiling point etc., dissolvent residual in the product is difficult to reach the requirement on the food applications like this, such product application can bring the problem on the safety in food ingredients, and the ratio of the cis-trans-isomer of fatty acid ester of lutein is subjected to the influence of raw material bigger in the product, as cis lutein content height in the raw material, then the biological activity of product can be affected.
In general, prior art all has following deficiency: product yield is not high; The organic solvent boiling point that uses in the method is higher, is difficult to remove fully when subsequent disposal; Higher dissolvent residual is arranged, be difficult to realize suitability for industrialized production.This is the problem that this area waits to solve.
Summary of the invention
The objective of the invention is to provides a kind of preparation method of high purity lutein ester at the deficiencies in the prior art part.
Purpose of the present invention is achieved by the following technical programs.
* except as otherwise noted, the percentage ratio that is adopted among the present invention is mass percent.
The invention provides a kind of method of purifying lutein esters, this method comprises the step of following order:
(1) under 25 ℃～80 ℃, the Flower of Aztec Marigold ointment is dissolved in the food grade ester class reagent, stirs 1～6 hour, forms uniform solution;
(2) will go up the solution that step obtains and under 30 ℃～80 ℃, carry out heat filtering;
(3) in the filtrate that last step obtains, add food grade alcohols reagent, stirred 0.5～5.0 hour down, form homogeneous solution at 20～70 ℃; Cool off 5～20 hours after-filtration down at-5～30 ℃;
(4) will go up step and filter the crystal obtain and wash, remove the impurity that is dissolved in lower alcohol with the lower alcohol of 1～4 carbon;
(5) will go up solid that step obtains at 25～55 ℃, dry under the vacuum tightness of-0.050～0.090MPa, remove and desolvate, promptly obtain required lutein ester.
Wherein, the material ratio (g/ml) of described Flower of Aztec Marigold ointment of step (1) and food grade Ester is 1: 1.5～1: 10; Described food grade ester is selected from a kind of in ethyl acetate, propyl acetate or the butylacetate or their mixture.
The amount of the food-grade alcohol that adds in the step (3) is 1～10 times of food grade ester, and described food-grade alcohol is selected from a kind of in methyl alcohol, ethanol, n-propyl alcohol or the propyl carbinol or their mixture.
The content assaying method of lutein ester of the present invention:
Accurately taking by weighing about 0.1g specimen is dissolved in normal hexane and makes 100ml solution.Use the normal hexane dilute sample, make gained solution absorbency scope between 0.3～0.7, and record near the absorbancy of above-mentioned diluting soln maximum absorption wavelength 445nm with spectrophotometer.
Lutein ester content calculates as follows:
Annotate: the A absorbancy, f is a dilution factor, and w is for claiming the sample quality, and 1394 is near the uptake factor of the maximum absorption wavelength 445nm.
Beneficial effect of the present invention:
1. effectively improved the purity of product, made lutein ester content reach 70%～80%;
2. the organic solvent of Cai Yonging is food grade ethanol and ethyl acetate, and solvent boiling point is low, easily removes in process of vacuum drying, and dissolvent residual is lower than the requirement of foodstuff additive and tinting material.
3. the simple easy handling of technology is for large-scale industrial production lays the first stone.
Embodiment
In order to make purpose of the present invention, technical scheme and advantage clearer, the present invention is further elaborated below in conjunction with embodiment.Should be appreciated that specific embodiment described herein only in order to explanation the present invention, and be not used in qualification the present invention.
Embodiment 1
Taking by weighing 101g Flower of Aztec Marigold ointment (total lutein ester content is 29.3%) mixes with 404ml food grade ethyl acetate, in 50 ℃ of following heating for dissolving, continue to stir 3 hours, remove insolubles at 70 ℃ of following heat filtering solution then, slowly add the food grade ethanol of 505ml, stir after 2.5 hours, under 5 ℃, left standstill 16 hours, the solid crystal that filtration is separated out is used 300ml propyl carbinol washing crystal at last.With vacuum drying oven drying solid crystal, drying temperature is 40 ℃, and is dry under the vacuum of 0.075MPa, obtains exsiccant solid matter 26.0g at last, and detecting its content with UV is 78.6%, and the yield of total lutein ester is 69.1%.
Embodiment 2
Taking by weighing 107g Flower of Aztec Marigold ointment (total lutein ester content is 29.3%) mixes with 428ml food grade ethyl acetate, in 50 ℃ of following heating for dissolving, continue to stir 3 hours, remove insolubles at 70 ℃ of following heat filtering solution then, slowly add the food grade ethanol of 535ml, stir after 2.5 hours, under 5 ℃, left standstill 16 hours, the solid crystal that filtration is separated out is used 300ml n-propyl alcohol washing crystal at last.With vacuum drying oven drying solid crystal, drying temperature is 40 ℃, and is dry under the vacuum of 0.075MPa, obtains the 21.3g crystal at last, and lutein ester content is 74.2%, and total xenthophylls yield is 50.4%.
Embodiment 3
Taking by weighing 103g Flower of Aztec Marigold ointment (total lutein ester content is 29.3%) mixes with 412ml food grade ethyl acetate, in 50 ℃ of following heating for dissolving, continue to stir 3 hours, remove insolubles at 70 ℃ of following heat filtering solution then, slowly add the food grade ethanol of 515ml, stir after 2.5 hours, under 5 ℃, left standstill 16 hours, the solid crystal that filtration is separated out is used 300ml washing with alcohol crystal at last.With vacuum drying oven drying solid crystal, drying temperature is 40 ℃, and is dry under the vacuum of 0.075MPa, obtains the 19.3g crystal at last, and lutein ester content is 71.7%, and total xenthophylls yield is 45.8%.
Embodiment 4
--wash without lower alcohol
Getting 103g Flower of Aztec Marigold ointment (total lutein ester content is 29.3%) mixes with 412ml food grade ethyl acetate, in 50 ℃ of following heating for dissolving, continue to stir 3 hours, remove insolubles at 70 ℃ of following heat filtering solution then, the food grade ethanol that slowly adds 515ml, stir after 2.5 hours, under 5 ℃, left standstill 16 hours, filter the solid crystal of separating out.With vacuum drying oven drying solid crystal, drying temperature is 40 ℃, and is dry under the vacuum of 0.075MPa, obtains the 27.2g crystal at last, and lutein ester content is 48.7%, and total xenthophylls yield is 43.89%.
Embodiment 5
--handle ointment, propyl carbinol washing crystal with the food grade propyl acetate
Taking by weighing 101g Flower of Aztec Marigold ointment (total lutein ester content is 29.3%) mixes with 404ml food grade propyl acetate, in 50 ℃ of following heating for dissolving, continue to stir 3 hours, remove insolubles at 70 ℃ of following heat filtering solution then, slowly add the food grade ethanol of 505ml, stir after 2.5 hours, under 5 ℃, left standstill 16 hours, the solid crystal that filtration is separated out is used 300ml propyl carbinol washing crystal at last.With vacuum drying oven drying solid crystal, drying temperature is 40 ℃, and is dry under the vacuum of 0.075MPa, obtains the 23.5g crystal at last, and lutein ester content is 73.7%, and total xenthophylls yield is 58.52%.
Embodiment 6
--handle ointment, n-propyl alcohol washing crystal with the food grade propyl acetate
Taking by weighing 108g Flower of Aztec Marigold ointment (total lutein ester content is 29.3%) mixes with 432ml food grade propyl acetate, in 50 ℃ of following heating for dissolving, continue to stir 3 hours, remove insolubles at 70 ℃ of following heat filtering solution then, slowly add the food grade ethanol of 540ml, stir after 2.5 hours, under 5 ℃, left standstill 16 hours, the solid crystal that filtration is separated out is used 300ml n-propyl alcohol washing crystal at last.With vacuum drying oven drying solid crystal, drying temperature is 40 ℃, and is dry under the vacuum of 0.075MPa, obtains the 23.1g crystal at last, and lutein ester content is 70.3%, and total xenthophylls yield is 51.32%.
Embodiment 7
--handle ointment, washing with alcohol crystal with the food grade propyl acetate
Taking by weighing 114g Flower of Aztec Marigold ointment (total lutein ester content is 29.3%) mixes with 456ml food grade propyl acetate, in 50 ℃ of following heating for dissolving, continue to stir 3 hours, remove insolubles at 70 ℃ of following heat filtering solution then, slowly add the food grade ethanol of 570ml, stir after 2.5 hours, under 5 ℃, left standstill 16 hours, the solid crystal that filtration is separated out is used 300ml washing with alcohol crystal at last.With vacuum drying oven drying solid crystal, drying temperature is 40 ℃, and is dry under the vacuum of 0.075MPa, obtains the 20.6g crystal at last, and lutein ester content is 63.3%, and total xenthophylls yield is 39.04%.
The above only is preferred embodiment of the present invention, not in order to restriction the present invention, all any modifications of being done within the spirit and principles in the present invention, is equal to and replaces and improvement etc., all should be included within protection scope of the present invention.
Claims (3)
1. the method for a purifying lutein esters is characterized in that, this method may further comprise the steps:
(1) under 25 ℃～80 ℃, the Flower of Aztec Marigold ointment is dissolved in the food grade ester class reagent, stirs 1～6 hour, forms uniform solution;
(2) will go up the solution that step obtains and under 30 ℃～80 ℃, carry out heat filtering;
(3) in the filtrate that last step obtains, add food grade alcohols reagent, stirred 0.5～5.0 hour down, form homogeneous solution at 20～70 ℃; Cool off 5～20 hours after-filtration down at-5～30 ℃;
(4) will go up step and filter the crystal obtain and wash, remove the impurity that is dissolved in lower alcohol with the lower alcohol of 1～4 carbon;
(5) will go up solid that step obtains at 25～55 ℃, dry under the vacuum tightness of-0.050～0.090MPa, remove and desolvate, promptly obtain required lutein ester.
2. method according to claim 1 is characterized in that, the material ratio (g/ml) of described Flower of Aztec Marigold ointment of step (1) and food grade Ester is 1: 1.5～1: 10; Described food grade ester is selected from a kind of in ethyl acetate, propyl acetate or the n-butyl acetate or their mixture.
3. method according to claim 1 is characterized in that, the amount of the food-grade alcohol that adds in the step (3) is 1～10 times of food grade ester, and described food-grade alcohol is selected from a kind of in methyl alcohol, ethanol, n-propyl alcohol or the propyl carbinol or their mixture.
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| CN201010232719XA CN101891664A (en) | 2010-07-21 | 2010-07-21 | Method for purifying lutein esters |
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| CN201010232719XA CN101891664A (en) | 2010-07-21 | 2010-07-21 | Method for purifying lutein esters |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102349647A (en) * | 2011-10-10 | 2012-02-15 | 大连医诺生物有限公司 | Combination containing lutein ester and preparation method thereof |
| CN102659653A (en) * | 2012-05-05 | 2012-09-12 | 邯郸市中进天然色素有限公司 | Purification method from lutein extractive to high-purity lutein ester |
| CN102757373A (en) * | 2012-07-31 | 2012-10-31 | 沈阳天峰生物制药有限公司 | Method for preparing high-purity lutein ester from marigold flower particles |
| CN103130699A (en) * | 2013-03-11 | 2013-06-05 | 大连医诺生物有限公司 | Food-grade high-content lutein ester and preparation method thereof |
| CN105418472A (en) * | 2015-11-21 | 2016-03-23 | 中国海洋大学 | Method for separating astaxanthin monoester and astaxanthin diester through fractional crystallization of solvent |
| CN106588732A (en) * | 2016-11-28 | 2017-04-26 | 云南瑞宝生物科技股份有限公司 | Method of purifying lutein ester from marigold ointment |
| CN106748947A (en) * | 2017-02-20 | 2017-05-31 | 青岛藻蓝生物有限公司 | A kind of method that efficient joint prepares high-purity lutein ester and lutein |
| CN107987002A (en) * | 2018-01-16 | 2018-05-04 | 邯郸市美康生物科技有限公司 | A kind of production method that high-purity lutein ester is prepared by marigold extractum |
| CN109134254A (en) * | 2018-09-28 | 2019-01-04 | 晨光生物科技集团股份有限公司 | A kind of industrial method preparing high-purity lutein ester |
| CN113527165A (en) * | 2021-07-14 | 2021-10-22 | 广州智特奇生物科技股份有限公司 | Lutein ester crystal form compound and preparation method and application thereof |
| WO2022155338A1 (en) | 2021-01-14 | 2022-07-21 | Kemin Industries, Inc. | Process for crystallization of high purity lutein esters from marigold extracts |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1432567A (en) * | 2002-01-08 | 2003-07-30 | 理研维他命株式会社 | Prepn process of lutein aliphatic ester concentrate |
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2010
- 2010-07-21 CN CN201010232719XA patent/CN101891664A/en active Pending
Patent Citations (1)
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| CN1432567A (en) * | 2002-01-08 | 2003-07-30 | 理研维他命株式会社 | Prepn process of lutein aliphatic ester concentrate |
Non-Patent Citations (1)
| Title |
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| 孙素玲等: "万寿菊中叶黄素酯的提取工艺研究", 《安徽农业科学》, vol. 37, no. 9, 31 December 2009 (2009-12-31), pages 3867 - 3868 * |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013053261A1 (en) * | 2011-10-10 | 2013-04-18 | 大连医诺生物有限公司 | Composition containing lutein ester and preparation method thereof |
| CN102349647B (en) * | 2011-10-10 | 2013-11-06 | 大连医诺生物有限公司 | Combination containing lutein ester and preparation method thereof |
| CN102349647A (en) * | 2011-10-10 | 2012-02-15 | 大连医诺生物有限公司 | Combination containing lutein ester and preparation method thereof |
| CN102659653A (en) * | 2012-05-05 | 2012-09-12 | 邯郸市中进天然色素有限公司 | Purification method from lutein extractive to high-purity lutein ester |
| CN102659653B (en) * | 2012-05-05 | 2013-11-06 | 邯郸市中进天然色素有限公司 | Purification method from lutein extractive to high-purity lutein ester |
| CN102757373A (en) * | 2012-07-31 | 2012-10-31 | 沈阳天峰生物制药有限公司 | Method for preparing high-purity lutein ester from marigold flower particles |
| CN103130699A (en) * | 2013-03-11 | 2013-06-05 | 大连医诺生物有限公司 | Food-grade high-content lutein ester and preparation method thereof |
| CN105418472B (en) * | 2015-11-21 | 2017-05-10 | 中国海洋大学 | Method for separating astaxanthin monoester and astaxanthin diester through fractional crystallization of solvent |
| CN105418472A (en) * | 2015-11-21 | 2016-03-23 | 中国海洋大学 | Method for separating astaxanthin monoester and astaxanthin diester through fractional crystallization of solvent |
| CN106588732A (en) * | 2016-11-28 | 2017-04-26 | 云南瑞宝生物科技股份有限公司 | Method of purifying lutein ester from marigold ointment |
| CN106748947A (en) * | 2017-02-20 | 2017-05-31 | 青岛藻蓝生物有限公司 | A kind of method that efficient joint prepares high-purity lutein ester and lutein |
| CN106748947B (en) * | 2017-02-20 | 2018-06-26 | 青岛藻蓝生物有限公司 | It is a kind of to combine the method for preparing lutein ester and lutein |
| CN107987002A (en) * | 2018-01-16 | 2018-05-04 | 邯郸市美康生物科技有限公司 | A kind of production method that high-purity lutein ester is prepared by marigold extractum |
| CN109134254A (en) * | 2018-09-28 | 2019-01-04 | 晨光生物科技集团股份有限公司 | A kind of industrial method preparing high-purity lutein ester |
| CN109134254B (en) * | 2018-09-28 | 2021-06-01 | 晨光生物科技集团股份有限公司 | Industrial method for preparing high-purity lutein ester |
| WO2022155338A1 (en) | 2021-01-14 | 2022-07-21 | Kemin Industries, Inc. | Process for crystallization of high purity lutein esters from marigold extracts |
| CN113527165A (en) * | 2021-07-14 | 2021-10-22 | 广州智特奇生物科技股份有限公司 | Lutein ester crystal form compound and preparation method and application thereof |
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