CN102757373A - 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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- CN102757373A CN102757373A CN2012102679018A CN201210267901A CN102757373A CN 102757373 A CN102757373 A CN 102757373A CN 2012102679018 A CN2012102679018 A CN 2012102679018A CN 201210267901 A CN201210267901 A CN 201210267901A CN 102757373 A CN102757373 A CN 102757373A
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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
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- 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 for preparing the high purity lutein ester by the marigold flower grain.
Background technology:
Lutein ester is a kind of important carrotenoid fatty ester.It extensively is present in the plant materialss such as pumpkin, spinach, wild cabbage, clover.Wherein, the abundantest with content in marigold flower.But human body effectively hydrolyzing lutein ester also discharges free xenthophylls, and research shows, takes in lutein ester and can improve the lutein levels in blood and the macula retinae, is playing an important role aspect prevention AMD, cancer-resisting, the enhancing human immune.
Up to now, having many is the patent report that raw material extracts lutein ester with the marigold extractum.For example CN1432567A uses the acetone extraction marigold oil resin, with the concentrated mother liquor of crystallization acetone such as butanols or Virahol, finally obtains the higher fatty acid ester of lutein enriched material of content through washing with alcohol again.Though 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, though use washing with alcohol at last, the residual requirement that still is difficult to reach the food applications aspect of the butanols in the product.CN101891664A washs filter cake with lower alcohol after the cooling of adding ethanol, crystallization, the filtration in heat-processed with acetic acid ethyl dissolution Flower of Aztec Marigold ointment again, when the lower alcohol washing leaching cake, has selected propyl carbinol for use, still has the residual problem of propyl carbinol.
CN1872839A is with normal hexane and the alcoholic acid mixing solutions lutein ester in the marigold oil resin that decrystallizes; Though the yield of the finished product is higher, the normal hexane in the product is difficult to reach in drying course in the Chinese new resource food standard for the requirement aspect the lutein ester normal hexane dissolvent residual.
In sum, all there is the lower or defective problem of organic solvent residual of yield in the method for existing preparation lutein ester.Therefore, it is high to await developing a kind of lutein ester content, and yield is high, and its organic solvent residual can reach the preparation method who requires in the Chinese food standard, to enlarge the use of Flower of Aztec Marigold.
Summary of the invention:
The technical problem that the present invention will solve provides and a kind ofly prepares the method for high purity lutein ester by the marigold flower grain, and this method is a raw material with the marigold flower grain, has saved the process of supercritical extraction marigold extractum; Reduced production cost and equipment cost, the organic solvent of employing is lower boiling three kind solvents, is prone to remove; Guaranteed security of products to the full extent, technology is simple to operation, is easy to industriallization; Product yield obviously is superior to the refining effect of prior art up to 90%.
Concrete steps of the present invention are following:
(1) under 50～80 ℃ of conditions, the marigold flower grain is mixed stirring extract 1-5h with ETHYLE ACETATE, filter, collect filtrating.
(2) vacuum concentrated filtrate to solid content is 30%.Filtrating after the partially concd is heated to 50～80 ℃, adds Virahol in the time of stirring heating, and the mixed solution that obtains continues under this temperature, to stir 0.5-1h.
(3) temperature that slowly reduces mixed solution is to-10-10 ℃, and under this temperature, keeps 2-5h to make its sufficient crystallising, and the crystallization after-filtration that finishes obtains filter cake 1.
(4) under 50～80 ℃ of conditions; Filter cake 1 and ETHYLE ACETATE/isopropyl alcohol mixed solvent are fully mixed 1-5h; The temperature that slowly reduces mixed solution again is to-10-10 ℃; And under this temperature, keeping 2-5h to make its sufficient crystallising, crystallization finishes filter cake 2 that after-filtration obtains through vacuum-dryings, finally obtains high purity lutein ester product.
The mass ratio of marigold flower grain and ETHYLE ACETATE is 1:5-10 in the step (1).
The add-on of the middle Virahol of step (2) is 0.5-2 a times of marigold flower grain quality.
The speed of cooling is 10-20 ℃/h in step (3), (4).
The mass ratio of ETHYLE ACETATE and Virahol is 1:1 in the step (4), and ETHYLE ACETATE/isopropyl alcohol mixed solvent add-on is 0.1-0.5 a times of marigold flower grain.
Vacuum drying condition in the step (4) is 20-40 ℃, 3-10h.
The content assaying method of lutein ester:
Accurately take by weighing about 0.1g specimen; Process 100ml solution with n-hexane dissolution; Make gained solution absorbency scope between 0.3-0.7 with the normal hexane dilute sample, with near the absorbancy of the above-mentioned diluting soln of spectrophotometric determination maximum absorption wavelength 445nm.
Lutein ester content calculates according to following formula:
Annotate: A-absorbancy, d-extension rate, the quality of W-specimen, 1394-specific absorbance;
The content of the lutein ester of measuring through as above method is high, and yield reaches more than 90%.
Embodiment:
Embodiment 1:
Take by weighing 1kg marigold flower grain (lutein ester content is 4.0%) and mix, be heated to 50 ℃ and stir extraction 5h after-filtration, collect filtrating with 5kg ETHYLE ACETATE; Vacuum concentration to the solid content of will filtrating is 30% post-heating to 60 ℃; Add the 500g Virahol in the time of heated and stirred, behind the insulated and stirred 0.5h, cool the temperature to 10 ℃ with the rate of temperature fall of 10 ℃/h; Keep the 5h after-filtration, obtain filter cake 1.The mixing solutions of filter cake 1 and 300g ETHYLE 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, under this temperature, keeps the 2h after-filtration, obtains filter cake 2; Filter cake 2 is through 20 ℃ of vacuum-drying 8h; Finally obtain the 52g crystal, the content of lutein ester is 70.5% in the crystal, pure yield 91.6%.
Embodiment 2:
Take by weighing 1kg marigold flower grain (lutein ester content is 4.0%) and mix, be heated to 70 ℃ and stir extraction 3h after-filtration, collect filtrating with 5kg ETHYLE ACETATE; Vacuum concentration to the solid content of will filtrating is 30% post-heating to 50 ℃; Add the 1kg Virahol in the time of heated and stirred, behind the insulated and stirred 1h, cool the temperature to 0 ℃ with the rate of temperature fall of 10 ℃/h; Keep the 2h after-filtration, obtain filter cake 1.The mixing solutions of filter cake 1 and 400g ETHYLE 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, under this temperature, keeps the 3h after-filtration, obtains filter cake 2; Filter cake 2 is through 30 ℃ of vacuum-drying 5h; Finally obtain the 50g crystal, the content of lutein ester is 72.5% in the crystal, pure yield 90.6%.
Embodiment 3:
Take by weighing 1kg marigold flower grain (lutein ester content is 4.0%) and mix, be heated to 60 ℃ and stir extraction 1h after-filtration, collect filtrating with 8kg ETHYLE ACETATE; Vacuum concentration to the solid content of will filtrating is 30% post-heating to 75 ℃; Add the 1.5kg Virahol in the time of heated and stirred, behind the insulated and stirred 0.5h, cool the temperature to 5 ℃ with the rate of temperature fall of 15 ℃/h; Keep the 4.5h after-filtration, obtain filter cake 1.The mixing solutions of filter cake 1 and 100g ETHYLE 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, under this temperature, keeps the 1h after-filtration, obtains filter cake 2; Filter cake 2 is through 40 ℃ of vacuum-drying 3h; Finally obtain the 51g crystal, the content of lutein ester is 70.0% in the crystal, pure yield 89.3%.
Embodiment 4:
Take by weighing 1kg marigold flower grain (lutein ester content is 4.0%) and mix, be heated to 80 ℃ and stir extraction 1h after-filtration, collect filtrating with 10kg ETHYLE ACETATE; Vacuum concentration to the solid content of will filtrating is 30% post-heating to 65 ℃; Add the 800g Virahol in the time of heated and stirred, behind the insulated and stirred 40min, cool the temperature to-5 ℃ with the rate of temperature fall of 18 ℃/h; Keep the 3h after-filtration, obtain filter cake 1.The mixing solutions of filter cake 1 and 450g ETHYLE 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, under this temperature, keeps the 4h after-filtration, obtains filter cake 2; Filter cake 2 is through 25 ℃ of vacuum-drying 10h; Finally obtain the 45g crystal, the content of lutein ester is 76.2% in the crystal, pure yield 85.7%.
Embodiment 5:
Take by weighing 1kg marigold flower grain (lutein ester content is 4.0%) and mix, be heated to 65 ℃ and stir extraction 4h after-filtration, collect filtrating with 9kg ETHYLE ACETATE; Vacuum concentration to the solid content of will filtrating is 30% post-heating to 80 ℃; Add the 500g Virahol in the time of heated and stirred, behind the insulated and stirred 0.5h, cool the temperature to-10 ℃ with the rate of temperature fall of 20 ℃/h; Keep the 2.5h after-filtration, obtain filter cake 1.The mixing solutions of filter cake 1 and 500g ETHYLE 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, under this temperature, keeps the 5h after-filtration, obtains filter cake 2; Filter cake 2 is through 32 ℃ of vacuum-drying 6h; Finally obtain the 44.4g crystal, the content of lutein ester is 75.6% in the crystal, pure yield 83.9%.
Embodiment 6:
Take by weighing 1kg marigold flower grain (lutein ester content is 4.0%) and mix, be heated to 70 ℃ and stir extraction 2h after-filtration, collect filtrating with 10kg ETHYLE ACETATE; Vacuum concentration to the solid content of will filtrating is 30% post-heating to 55 ℃; Add the 2kg Virahol in the time of heated and stirred, behind the insulated and stirred 50min, cool the temperature to 8 ℃ with the rate of temperature fall of 12 ℃/h; Keep the 5h after-filtration, obtain filter cake 1.The mixing solutions of filter cake 1 and 200g ETHYLE 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, under this temperature, keeps the 3.5h after-filtration, obtains filter cake 2; Filter cake 2 is through 40 ℃ of vacuum-drying 3h; Finally obtain the 48g crystal, the content of lutein ester is 74.5% in the crystal, pure yield 89.4%.
Embodiment 7:
The content and the yield simultaneous test of the prepared lutein ester of different preparing methods in the prior art.
The result shows: the present invention has obviously improved the yield of product with respect to preparation method of the prior art.
Claims (6)
1. one kind prepares the method for high purity lutein ester by the marigold flower grain, it is characterized in that this method may further comprise the steps:
(1) under 50～80 ℃ of conditions, the marigold flower grain is mixed stirring extract 1-5h with ETHYLE ACETATE, filter, collect filtrating;
(2) vacuum concentrated filtrate to solid content is 30%, and the filtrating after the partially concd is heated to 50～80 ℃, adds Virahol in the time of stirring heating, and the mixed solution that obtains continues under this temperature, to stir 0.5-1h;
(3) temperature that slowly reduces mixed solution is to-10-10 ℃, and under this temperature, keeps 2-5h to make its sufficient crystallising, and the crystallization after-filtration that finishes obtains filter cake 1;
(4) under 50～80 ℃ of conditions; Filter cake 1 and ETHYLE ACETATE/isopropyl alcohol mixed solvent are fully mixed 1-5h; The temperature that slowly reduces mixed solution again is to-10-10 ℃; And under this temperature, keeping 2-5h to make its sufficient crystallising, crystallization finishes filter cake 2 that after-filtration obtains through vacuum-dryings, finally obtains high purity lutein ester product.
2. according to claim 1ly a kind ofly prepare the method for high purity lutein ester, it is characterized in that the mass ratio of marigold flower grain and ETHYLE ACETATE is 1:5-10 in its step (1) by the marigold flower grain.
3. according to claim 1ly a kind ofly prepare the method for high purity lutein ester by the marigold flower grain, the adding quality that it is characterized in that Virahol in its step (2) be marigold flower grain quality 0.5-2 doubly.
4. according to claim 1ly a kind ofly prepare the method for high purity lutein ester, it is characterized in that speed of cooling in its step (3), (4) is 10-20 ℃/h by the marigold flower grain.
5. a kind of method for preparing the high purity lutein ester by the marigold flower grain according to claim 1; The mass ratio that it is characterized in that middle ETHYLE ACETATE of its step (4) and Virahol is 1:1, and ETHYLE ACETATE/isopropyl alcohol mixed solvent add-on is 0.1-0.5 a times of marigold flower grain.
6. according to claim 1ly a kind ofly prepare the method for high purity lutein ester, it is characterized in that the vacuum drying condition in its step (4) is 20-40 ℃, 3-10h by the marigold flower grain.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| WO2022155338A1 (en) | 2021-01-14 | 2022-07-21 | Kemin Industries, Inc. | Process for crystallization of high purity lutein esters from marigold extracts |
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| 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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Patent Citations (5)
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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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
| 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 |
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