CN102757373B - Method for preparing high-purity lutein ester from marigold flower particles - Google Patents
Method for preparing high-purity lutein ester from marigold flower particles Download PDFInfo
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- CN102757373B CN102757373B CN201210267901.8A CN201210267901A CN102757373B CN 102757373 B CN102757373 B CN 102757373B CN 201210267901 A CN201210267901 A CN 201210267901A CN 102757373 B CN102757373 B CN 102757373B
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Abstract
The invention belongs to the technical field of medicine, and relates to a method for preparing high-purity lutein ester from marigold flower particles. The method comprises the following steps of: mixing, stirring and extracting marigold flower particles and acetic ether, filtering, and collecting a filtrate; concentrating the filtrate in vacuum till the solid content is 30 percent; adding isopropyl alcohol while stirring and heating a part of the concentrated filtrate to obtain a mixed solution, and continuously stirring the mixed solution at the same temperature for 0.5-1 hour; lowering the temperature of the mixed solution, keeping the temperature for 2-5 hours for crystalizing fully, and filtering to obtain a filter cake 1; and fully stirring and mixing the filter cake 1 and an acetic ether/isopropyl alcohol mixed solvent for 1-5 hours, lowering the temperature of the mixed solution, keeping the temperature for 2-5 hours for fully crystalizing, filtering after crystalizing to obtain a filter cake 2, and drying the filter cake 2 in vacuum to obtain a high-purity lutein ester product finally. Due to the adoption of the method, the process for extracting a marigold flower extract in a supercritical is eliminated, and production cost and equipment cost are reduced; and all adopted organic solvents are type III solvents with low boiling points and are easy to remove, a process is simple and is easy to operate, and the product yield is up to 90 percent.
Description
Technical field:
The invention belongs to medical technical field, relate to a kind of method of being prepared high purity lutein ester by marigold flower grain.
Background technology:
Lutein ester is a kind of important carotenoid fatty acid ester.It is extensively present in the plant materialss such as pumpkin, spinach, wild cabbage, clover.Wherein, the abundantest with content in marigold flower.Human body can effectively hydrolyzing lutein ester and is discharged free xenthophylls, and research shows, takes in lutein ester and can improve the lutein levels in blood and macula retinae, aspect prevention AMD, cancer-resisting, enhancing body immunity, is playing an important role.
Up to now, there are the many patent reports of marigold extractum as raw material extraction lutein ester of take.CN1432567A acetone extraction marigold oil resin for example, then with the concentrated mother liquor of the crystallization acetone such as butanols or Virahol, through washing with alcohol, finally obtain the fatty acid ester of lutein enriched material that content is higher.Although the lutein ester product content that this method obtains is very high, yield is lower, and in crystallisation process, has used the higher butanols of boiling point, although finally use washing with alcohol, the residual requirement that is still difficult to reach food applications aspect of butanols in product.Acetic acid ethyl dissolution Flower of Aztec Marigold ointment for CN101891664A, with lower alcohol to filter cake washs after adding ethanol cooling, crystallization, filtration in heat-processed again, when lower alcohol washing leaching cake, has selected propyl carbinol, still has the residual problem of propyl carbinol.
The lutein ester that CN1872839A decrystallizes in marigold oil resin with the mixing solutions of normal hexane and ethanol, although the yield of the finished product is higher, the normal hexane in product is difficult to reach in Chinese new resource food standard for the requirement aspect lutein ester normal hexane dissolvent residual in drying course.
In sum, all there is the lower or defective problem of organic solvent residual of yield in the existing method of preparing lutein ester.Therefore, await developing a kind of lutein ester content high, yield is high, and its organic solvent residual can reach the preparation method who requires in Chinese food standard, to expand the use of Flower of Aztec Marigold.
Summary of the invention:
The technical problem to be solved in the present invention is to provide a kind of method of being prepared high purity lutein ester by marigold flower grain, the method be take marigold flower grain as raw material, the process of having saved supercritical extraction marigold extractum, has reduced production cost and equipment cost, and the organic solvent of employing is lower boiling three kind solvents, easily remove, guaranteed to the full extent the security of product, technique is simple to operation, is easy to industrialization, product yield, up to 90%, is obviously better than the refining effect of prior art.
Concrete steps of the present invention are as follows:
(1) under 50～80 ℃ of conditions, marigold flower grain and ethyl acetate mix and blend are extracted to 1-5h, filter, collect filtrate.
(2) vacuum concentrated filtrate to solid content is 30%.Filtrate after partial concentration is heated to 50～80 ℃, adds Virahol in the time of stirring heating, and the mixed solution obtaining continues to stir 0.5-1h at this temperature.
(3) temperature that slowly reduces mixed solution is to-10-10 ℃, and at this temperature, keeps 2-5h to make its sufficient crystallising, after crystallization, filters, and obtains filter cake 1.
(4) under 50～80 ℃ of conditions, filter cake 1 and ethyl acetate/isopropyl alcohol mixed solvent are fully uniformly mixed to 1-5h, the temperature that slowly reduces again mixed solution is to-10-10 ℃, and at this temperature, keep 2-5h to make its sufficient crystallising, after crystallization, filter the filter cake 2 process vacuum-dryings that obtain, finally obtain high purity lutein ester product.
In step (1), the mass ratio of marigold flower grain and ethyl acetate is 1:5-10.
The add-on of the middle Virahol of step (2) is 0.5-2 times of marigold flower grain quality.
In step (3), (4), the speed of cooling is 10-20 ℃/h.
In step (4), the mass ratio of ethyl acetate and Virahol is 1:1, and ethyl acetate/isopropyl alcohol mixed solvent add-on is 0.1-0.5 times of marigold flower grain.
Vacuum drying condition in step (4) is 20-40 ℃, 3-10h.
The content assaying method of lutein ester:
Accurately take about 0.1g test sample, with n-hexane dissolution, make 100ml solution, with normal hexane dilute sample, make the range of absorbency of gained solution between 0.3-0.7, by near the absorbancy of the above-mentioned diluting soln of spectrophotometric determination maximum absorption wavelength 445nm.
Lutein ester content calculates according to following formula:
Note: A-absorbancy, d-extension rate, the quality of W-test sample, 1394-specific absorbance;
Content by the lutein ester that as above method is measured is high, and yield reaches more than 90%.
Embodiment:
Embodiment 1:
Taking 1kg marigold flower grain (lutein ester content is 4.0%) mixes with 5kg ethyl acetate, be heated to after 5h is extracted in 50 ℃ of stirrings filter, collect filtrate, by filtrate vacuum concentration to solid content, it is 30% post-heating to 60 ℃, in the time of heated and stirred, add 500g Virahol, after insulated and stirred 0.5h, with the rate of temperature fall of 10 ℃/h, cool the temperature to 10 ℃, keep filtering after 5h, obtain filter cake 1.The mixing solutions of filter cake 1 and 300g ethyl acetate/Virahol (mass ratio 5:5) is heated with stirring to 80 ℃ and keep 1h, rate of temperature fall with 10 ℃/h cools the temperature to-10 ℃ again, keep 2h at this temperature after, filter, obtain filter cake 2, filter cake 2 is through 20 ℃ of vacuum-drying 8h, finally obtain 52g crystal, the content of crystal Lutein ester is 70.5%, pure yield 91.6%.
Embodiment 2:
Taking 1kg marigold flower grain (lutein ester content is 4.0%) mixes with 5kg ethyl acetate, be heated to after 3h is extracted in 70 ℃ of stirrings filter, collect filtrate, by filtrate vacuum concentration to solid content, it is 30% post-heating to 50 ℃, in the time of heated and stirred, add 1kg Virahol, after insulated and stirred 1h, with the rate of temperature fall of 10 ℃/h, cool the temperature to 0 ℃, keep filtering after 2h, obtain filter cake 1.The mixing solutions of filter cake 1 and 400g ethyl acetate/Virahol (mass ratio 5:5) is heated with stirring to 70 ℃ and keep 1h, rate of temperature fall with 15 ℃/h cools the temperature to 0 ℃ again, keep 3h at this temperature after, filter, obtain filter cake 2, filter cake 2 is through 30 ℃ of vacuum-drying 5h, finally obtain 50g crystal, the content of crystal Lutein ester is 72.5%, pure yield 90.6%.
Embodiment 3:
Taking 1kg marigold flower grain (lutein ester content is 4.0%) mixes with 8kg ethyl acetate, be heated to after 1h is extracted in 60 ℃ of stirrings filter, collect filtrate, by filtrate vacuum concentration to solid content, it is 30% post-heating to 75 ℃, in the time of heated and stirred, add 1.5kg Virahol, after insulated and stirred 0.5h, with the rate of temperature fall of 15 ℃/h, cool the temperature to 5 ℃, keep filtering after 4.5h, obtain filter cake 1.The mixing solutions of filter cake 1 and 100g ethyl acetate/Virahol (mass ratio 5:5) is heated with stirring to 75 ℃ and keep 3h, rate of temperature fall with 20 ℃/h cools the temperature to-4 ℃ again, keep 1h at this temperature after, filter, obtain filter cake 2, filter cake 2 is through 40 ℃ of vacuum-drying 3h, finally obtain 51g crystal, the content of crystal Lutein ester is 70.0%, pure yield 89.3%.
Embodiment 4:
Taking 1kg marigold flower grain (lutein ester content is 4.0%) mixes with 10kg ethyl acetate, be heated to after 1h is extracted in 80 ℃ of stirrings filter, collect filtrate, by filtrate vacuum concentration to solid content, it is 30% post-heating to 65 ℃, in the time of heated and stirred, add 800g Virahol, after insulated and stirred 40min, with the rate of temperature fall of 18 ℃/h, cool the temperature to-5 ℃, keep filtering after 3h, obtain filter cake 1.The mixing solutions of filter cake 1 and 450g ethyl acetate/Virahol (mass ratio 5:5) is heated with stirring to 60 ℃ and keep 5h, rate of temperature fall with 10 ℃/h cools the temperature to 7 ℃ again, keep 4h at this temperature after, filter, obtain filter cake 2, filter cake 2 is through 25 ℃ of vacuum-drying 10h, finally obtain 45g crystal, the content of crystal Lutein ester is 76.2%, pure yield 85.7%.
Embodiment 5:
Taking 1kg marigold flower grain (lutein ester content is 4.0%) mixes with 9kg ethyl acetate, be heated to after 4h is extracted in 65 ℃ of stirrings filter, collect filtrate, by filtrate vacuum concentration to solid content, it is 30% post-heating to 80 ℃, in the time of heated and stirred, add 500g Virahol, after insulated and stirred 0.5h, with the rate of temperature fall of 20 ℃/h, cool the temperature to-10 ℃, keep filtering after 2.5h, obtain filter cake 1.The mixing solutions of filter cake 1 and 500g ethyl acetate/Virahol (mass ratio 5:5) is heated with stirring to 50 ℃ and keep 4h, rate of temperature fall with 10 ℃/h cools the temperature to 10 ℃ again, keep 5h at this temperature after, filter, obtain filter cake 2, filter cake 2 is through 32 ℃ of vacuum-drying 6h, finally obtain 44.4g crystal, the content of crystal Lutein ester is 75.6%, pure yield 83.9%.
Embodiment 6:
Taking 1kg marigold flower grain (lutein ester content is 4.0%) mixes with 10kg ethyl acetate, be heated to after 2h is extracted in 70 ℃ of stirrings filter, collect filtrate, by filtrate vacuum concentration to solid content, it is 30% post-heating to 55 ℃, in the time of heated and stirred, add 2kg Virahol, after insulated and stirred 50min, with the rate of temperature fall of 12 ℃/h, cool the temperature to 8 ℃, keep filtering after 5h, obtain filter cake 1.The mixing solutions of filter cake 1 and 200g ethyl acetate/Virahol (mass ratio 5:5) is heated with stirring to 65 ℃ and keep 2h, rate of temperature fall with 15 ℃/h cools the temperature to 5 ℃ again, keep 3.5h at this temperature after, filter, obtain filter cake 2, filter cake 2 is through 40 ℃ of vacuum-drying 3h, finally obtain 48g crystal, the content of crystal Lutein ester is 74.5%, pure yield 89.4%.
Embodiment 7:
Content and the yield simultaneous test of the prepared lutein ester of different preparation methods in prior art.
Result shows: the present invention has obviously improved the yield of product with respect to preparation method of the prior art.
Claims (3)
1. by marigold flower grain, prepared a method for lutein ester, it is characterized in that the method comprises the following steps:
(1) under 50～80 ℃ of conditions, marigold flower grain and ethyl acetate mix and blend are extracted to 1-5h, filter, collect filtrate;
(2) vacuum concentrated filtrate to solid content is 30%, and the filtrate after partial concentration is heated to 50～80 ℃, adds Virahol in the time of stirring heating, and the mixed solution obtaining continues to stir 0.5-1h at this temperature;
(3) temperature that slowly reduces mixed solution is to-10-10 ℃, and at this temperature, keeps 2-5h to make its sufficient crystallising, after crystallization, filters, and obtains filter cake 1;
(4) under 50～80 ℃ of conditions, filter cake 1 and ethyl acetate/isopropyl alcohol mixed solvent are fully uniformly mixed to 1-5h, the temperature that slowly reduces again mixed solution is to-10-10 ℃, and at this temperature, keep 2-5h to make its sufficient crystallising, after crystallization, filter the filter cake 2 process vacuum-dryings that obtain, finally obtain lutein ester product; Wherein, in step (1), the mass ratio of marigold flower grain and ethyl acetate is 1:5-10;
In step (2) Virahol add quality be marigold flower grain quality 0.5-2 doubly;
In step (4), the mass ratio of ethyl acetate and Virahol is 1:1, and ethyl acetate/isopropyl alcohol mixed solvent add-on is 0.1-0.5 times of marigold flower grain.
2. a kind of method of being prepared lutein ester by marigold flower grain according to claim 1, is characterized in that the speed of cooling in its step (3), (4) is 10-20 ℃/h.
3. a kind of method of being prepared lutein ester by marigold flower grain according to claim 1, is characterized in that the vacuum drying condition in its step (4) is 20-40 ℃, 3-10h.
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| CN104059007A (en) * | 2014-04-30 | 2014-09-24 | 西安岳达植物科技有限公司 | Method for extracting lutein ester from marigold flowers |
| 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 |
| US20220220059A1 (en) | 2021-01-14 | 2022-07-14 | Kemin Industries, Inc. | Process for crystallization of high purity lutein esters from marigold extracts |
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| US5648564A (en) * | 1995-12-21 | 1997-07-15 | Kemin Industries, Inc. | Process for the formation, isolation and purification of comestible xanthophyll crystals from plants |
| CN1082507C (en) * | 1996-10-04 | 2002-04-10 | 霍夫曼-拉罗奇有限公司 | Converting method for lutein |
| US6380442B1 (en) * | 2001-10-10 | 2002-04-30 | Bioactives, Llc | Process for the isolation of mixed carotenoids from plants |
| CN1309693C (en) * | 2002-02-05 | 2007-04-11 | 海宁凤鸣叶绿素有限公司 | Lutein crystal preparing process from marigold flower |
| CN101891664A (en) * | 2010-07-21 | 2010-11-24 | 云南瑞宝生物科技有限公司 | Method for purifying lutein esters |
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