CN103992256A - Method for preparing high-purity lutein esters from pot marigold - Google Patents
Method for preparing high-purity lutein esters from pot marigold Download PDFInfo
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- CN103992256A CN103992256A CN201410209053.4A CN201410209053A CN103992256A CN 103992256 A CN103992256 A CN 103992256A CN 201410209053 A CN201410209053 A CN 201410209053A CN 103992256 A CN103992256 A CN 103992256A
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- lutein ester
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Abstract
The invention relates to a method for preparing high-purity lutein esters from pot marigold and belongs to the technical fields of food, health-care food and phytochemistry. The method comprises the following steps: a, taking fresh pot marigold, adding ethanol for extracting so as to obtain an extract, and then concentrating the extract, thereby obtaining a concentrated liquor; b, adding the concentrated liquor to water at a temperature less than or equal to 10 DEG C, mixing evenly to obtain a suspension, and then adding active carbon to the suspension for adsorption, and filtering to obtain filter residue; c, putting the filter residue in chromatographic column, eluting by using a 60-95wt% ethanol solution at a temperature less than or equal to 10 DEG C firstly, then eluting by using an acetone-ethanol solution, collecting eluates, and concentrating to obtain a crude extract; d, dissolving the crude extract by using 10-90wt% acetone-ethanol solution, crystallizing, filtering and drying, thereby obtaining lutein esters. The method has the beneficial effects of simplicity and convenience in operation and high purity of the obtained lutein esters.
Description
Technical field
The invention belongs to food, protective foods and vegetable chemistry technical field, be specifically related to a kind of method of preparing high purity lutein ester from Potmarigold Calendula.
Background technology
Xenthophylls belongs to the tetraterpenes compound of carotenoids, is extensively present in flower, leaf, fruit and some algae bio of plant.Research shows, that xenthophylls has is painted, anti-oxidant, eyeshield, anti-cardiovascular disease and the several functions such as anticancer, is widely used in the fields such as food, medicine, healthcare products, makeup and aquaculture.Potmarigold Calendula petal Lutein content is especially abundant, is the main source of xenthophylls plant extract in recent years.Plant Lutein exists with the form of lutein ester, and because lutein ester must just can be absorbed by the body through being hydrolyzed to xenthophylls in human body, in existing xenthophylls preparation technology, the general method of lutein ester alkalescence saponification that adopts obtains free xenthophylls.
In China market, xenthophylls product purity is many below 90% at present, how as primary raw materials outlet, can not enter external main flow pigment product market.The existing various technology of China are difficult to obtain high purity lutein ester, and in leaching process, can introduce a lot of impurity is common problem.Because these impurity are not removed before saponification process, affect saponification effect on the one hand, increase on the other hand the difficulty of follow-up xenthophylls purifying process, and reduced yield.Therefore, how to obtain high purity lutein ester and just become the industry key issue that obtains high purity lutein.
Lutein ester is many at present extracts by solvent extration, obtains free lutein, then obtain lutein crystal through operations such as extraction or recrystallizations after extract saponification.Wherein:
Application number is that 201210257183.6 Chinese patent discloses a kind of method of being prepared crystal lutein by marigold flower particle, and it adds alkaline aqueous solution in marigold particles, carries out saponification; Then add salt solution, after stirring, filter, obtain filter cake; With the described filter cake of alkane solvents extraction, filter and obtain degrease filter cake; This degrease filter cake extracts with tetrahydrofuran (THF), is extracted liquid, and extraction liquid washes rear recrystallization with water, then fractional crystallization, dry, obtains lutein crystal.The shortcomings such as it is loaded down with trivial details that this preparation method exists technological operation, and solvent load is large, recrystallization length consuming time.
Application number is that 201310076600.1 Chinese patent discloses a kind of food grade high-content lutein ester and preparation method thereof, C2-4 alcoholic solvent will be added in marigold extractum, under 30～60 ℃ of conditions, agitator treating 3～6 hours or supersound process are 1～2 hour, after being cooled to 30～50 ℃, filter, obtain filter cake I; In filter cake I, add methyl alcohol or washing with alcohol 1～3 time, filter, obtain filter cake II; Filter cake II drying, except desolventizing, obtains lutein ester content and is about 80% left and right.
In sum, the precondition of preparing high purity lutein is to obtain highly purified lutein ester, finding the lutein ester preparation method that technological operation is easy, solvent load is few, product purity is high, is the key issue that improves Potmarigold Calendula plant resources utilization rate, realizes high purity lutein large-scale industrialized production.
Summary of the invention
The object of this invention is to provide a kind of method of preparing high purity lutein ester from Potmarigold Calendula, the method is easy and simple to handle, and gained lutein ester purity is high.
The technical solution used in the present invention is a kind of method of preparing high purity lutein ester from Potmarigold Calendula, comprises the following steps:
A, get fresh Potmarigold Calendula, add extraction using alcohol, obtain extracting solution, then described extracting solution is concentrated, obtain concentrated solution;
B, described concentrated solution is added to the water of temperature≤10 ℃, mix, obtain suspension, then in this suspension, add charcoal absorption, filter, obtain filter residue; Wherein, the add-on of water be concentrated solution volume 1/2-2 doubly.
C, described filter residue is placed in to chromatography column, with the mass percent concentration of temperature≤10 ℃, is first 60%～95% ethanolic soln wash-out, then uses acetone-ethanolic soln wash-out, collect elutriant, concentrated, obtain crude extract; Wherein, while adopting acetone-ethanolic soln wash-out, acetone-ethanolic soln, by the acetone of 60～90 parts by volume and the ethanol of 100 parts by volume, mixes.
D, the acetone-dissolve with ethanol solution that is 10%～90% with mass percent concentration by described crude extract, crystallization, filters, dry, obtains.
As preferably, in described step a, the add-on of ethanol is 2～10 times of weight of described Potmarigold Calendula weight.Particularly preferred, the add-on of ethanol is 3 times, 4 times, 5 times, 6 times, 7 times, 8 times and 9 times of described Potmarigold Calendula weight.
As preferably, the time of extracting in described step a is 1～3 hour, the temperature of extraction is 30 ℃～60 ℃, is extracted in vacuum condition and gets off to carry out.Particularly preferred, the time of extraction is 2 hours, and the temperature of extraction is 40 ℃ and 50 ℃.
As preferably, in described step a, the volume of concentrated solution is described extracting liquid volume 1/3～1/5.
As preferably, in described step b, the add-on of gac adds the gac of 1～10 weight part to carry out according to suspension described in every 100 parts by volume.Particularly preferred, the add-on of gac adds 2 weight part gacs, 3 weight part gacs, 4 weight part gacs, 5 weight part gacs, 6 weight part gacs, 7 weight part gacs, 8 weight part gacs and 9 weight part gacs according to suspension described in every 100 parts by volume.
As preferably, the number of times that described gac adds is 1～3 time.Particularly preferred, the indegree that adds of gac is 2 times.
As preferably, at described gac, be added to after described suspension, stir 10～30min.
As preferably, in described step c, concentrate and adopt the mode of concentrating under reduced pressure to carry out.
As preferably, in described step a, before extraction using alcohol, also comprise oven dry, the step of pulverizing.
The present invention also provides a kind of lutein ester being obtained by above-mentioned preparation method, by percentage to the quality, this lutein ester comprises tetradecanoic acid cetylate 25%～35%, dipalmitate 25%～41%, two myristinates 10%～28%, palmitinic acid stearate 8%～19%.
It is material that the present invention adopts Potmarigold Calendula, in Potmarigold Calendula, be rich in lutein ester, its lutein ester comprises the compositions such as tetradecanoic acid cetylate, dipalmitate, two myristinates, palmitinic acid stearate, SUNSOFT Q-182S, single nutmeg acid esters, monopalmitate and monostearate.
Xenthophylls in Potmarigold Calendula and ester thereof are all more responsive to photo-thermal, easily in extracting preparation process, transform, go bad.The present invention by control oxygen in air and contact with material and leaching process in temperature, effectively solved the conversion of leaching process Lutein ester, rotten problem.Meanwhile, adopt ethanol but not the low boiling point solvents such as sherwood oil, acetone, normal hexane have reduced solvent loss and the measures for the prevention of explosion in production process, reduced production difficulty, saved production cost.
Beneficial effect of the present invention is: the present invention utilizes the high-affinity of lutein ester and gac, can in alcohol-water mixture, combine closely with gac, thereby realize easy, quick, effectively separated with most polar impurities; Simultaneously the present invention utilizes the impurity such as chlorophyll and lutein ester adsorptivity different on gac, pass through chromatographic separation, can remove most oil-soluble impuritieses, by Crystallization Procedure, remove a small amount of residual impurity again, thereby obtain highly purified lutein ester, for the utilization of lutein ester and the preparation of high purity lutein product have solved key issue.
Embodiment
For making those skilled in the art understand in detail production technique of the present invention and technique effect, with concrete production instance, further introduce application of the present invention and technique effect below.
Embodiment 1:
A, get fresh Potmarigold Calendula 1kg, the ethanol that the mass percent concentration that adds 8 times of weight is 95% extracts 1 hour in 50 ℃ of heating under vacuum condition, filters, obtain extracting solution, then described extracting solution is concentrated, be concentrated into 1/3 of extracting liquid volume, obtain concentrated solution.
B, described concentrated solution is added to the water of 10 ℃ of temperature, mix, obtain suspension, then according to every 100 parts by volume suspensions, add the amount of 7 weight part gacs, in this suspension, add charcoal absorption, filter, obtain filter residue; Wherein, the number of times that gac adds is 3 times.Wherein, the add-on of water is 1 times of concentrated solution volume.
C, described filter residue is placed in to chromatography column, the ethanolic soln wash-out that is first 60% with the mass percent concentration that temperature is 10 ℃, then use acetone-ethanolic soln wash-out, and through TLC, follow the tracks of, collect target elutriant, concentrating under reduced pressure, obtains crude extract; Wherein, acetone-ethanolic soln is mixed by the acetone of 80 parts by volume and the ethanol of 100 parts by volume.
D, the acetone-dissolve with ethanol solution that is 20% with mass percent concentration by described crude extract, crystallization, filters, dry, obtains 5.88g lutein ester.
After testing, the purity of this lutein ester is 99%, and its content that comprises tetradecanoic acid cetylate is 35%, dipalmitate 30%, two myristinate 18%, palmitinic acid stearate 15%.
Embodiment 2:
A, get fresh Potmarigold Calendula 1kg, dry, be crushed to 60 orders, the ethanol that the mass percent concentration that adds 10 times of weight is 95% extracts 3 hours in 30 ℃ of heating under vacuum condition, filters, and obtains extracting solution, then described extracting solution is concentrated, be concentrated into 1/5 of extracting liquid volume, obtain concentrated solution.
B, described concentrated solution is added to the water of 8 ℃ of temperature, mix, obtain suspension, then according to every 100 parts by volume suspensions, add the amount of 1 weight part gac, in this suspension, add charcoal absorption, filter, obtain filter residue; Wherein, the add-on of water is 2 times of concentrated solution volume; The number of times that gac adds is 3 times.
C, described filter residue is placed in to chromatography column, the ethanolic soln wash-out that is first 95% with the mass percent concentration that temperature is 5 ℃, then use acetone-ethanolic soln wash-out, and through TLC, follow the tracks of, collect target elutriant, concentrating under reduced pressure, obtains crude extract; Wherein, acetone-ethanolic soln is mixed by the acetone of 60 parts by volume and the ethanol of 100 parts by volume.
D, the acetone-dissolve with ethanol solution that is 50% with mass percent concentration by described crude extract, crystallization, filters, dry, obtains 5.93g lutein ester.
After testing, the purity of this lutein ester is 98%, and its content that comprises tetradecanoic acid cetylate is 25%, dipalmitate 38%, two myristinate 27%, palmitinic acid stearate 8%.
Embodiment 3:
A, get fresh Potmarigold Calendula 1kg, dry, be crushed to 20 orders, the ethanol that the mass percent concentration that adds 2 times of weight is 90% extracts 3 times in 50 ℃ of heating under vacuum condition, extracts 2 hours at every turn, filters, obtain extracting solution, then described extracting solution is concentrated, be concentrated into 1/4 of extracting liquid volume, obtain concentrated solution.
B, described concentrated solution is added to the water of 2 ℃ of temperature, mix, obtain suspension, then according to every 100 parts by volume suspensions, add the amount of 10 weight part gacs, in this suspension, add charcoal absorption, filter, obtain filter residue; Wherein, the add-on of water is 1/2 of concentrated solution volume; The number of times that gac adds is 2 times.
C, described filter residue is placed in to chromatography column, the ethanolic soln wash-out that is first 75% with the mass percent concentration that temperature is 2 ℃, then use acetone-ethanolic soln wash-out, and through TLC, follow the tracks of, collect target elutriant, concentrating under reduced pressure, obtains crude extract; Wherein, acetone-ethanolic soln is mixed by the acetone of 90 parts by volume and the ethanol of 100 parts by volume.
D, the acetone-dissolve with ethanol solution that is 90% with mass percent concentration by described crude extract, crystallization, filters, dry, obtains 6.03g lutein ester.
After testing, the purity of this lutein ester is 99%, and its content that comprises tetradecanoic acid cetylate is 30%, dipalmitate 25%, two myristinate 25%, palmitinic acid stearate 19%.
Embodiment 4:
A, get fresh Potmarigold Calendula 1kg, dry, to the moisture content of Potmarigold Calendula, lower than 10%, be crushed to 40 orders, the ethanol that the mass percent concentration that adds 6 times of weight is 85% extracts 2 times in 40 ℃ of heating under vacuum condition, each extraction 2 hours, filter, obtain extracting solution, then described extracting solution is concentrated, be concentrated into 1/3 of extracting liquid volume, obtain concentrated solution.
B, described concentrated solution is added to the water of 0 ℃ of temperature, mix, obtain suspension, then according to every 100 parts by volume suspensions, add the amount of 4 weight part gacs, in this suspension, add charcoal absorption, filter, obtain filter residue; Wherein, the add-on of water is 1.5 times of concentrated solution volume; The number of times that gac adds is 3 times.
C, described filter residue is placed in to chromatography column, the ethanolic soln wash-out that is first 85% with the mass percent concentration that temperature is 2 ℃, then use acetone-ethanolic soln wash-out, and through TLC, follow the tracks of, collect target elutriant, concentrating under reduced pressure, obtains crude extract; Wherein, acetone-ethanolic soln is mixed by the acetone of 85 parts by volume and the ethanol of 100 parts by volume.
D, the acetone-dissolve with ethanol solution that is 90% with mass percent concentration by described crude extract, crystallization, filters, dry, obtains 6.11g lutein ester.
After testing, the purity of this lutein ester is 99%, and its content that comprises tetradecanoic acid cetylate is 30%, dipalmitate 25%, two myristinate 25%, palmitinic acid stearate 19%.
The purity of above-described embodiment gained lutein ester is high, and the component of formation is clear and definite, and the lutein ester of comparing existing preparation has significant technical progress.
Finally it should be noted that, above embodiment is the unrestricted technical scheme of the present invention in order to explanation only, although the present invention is had been described in detail with reference to above-described embodiment, those skilled in the art are to be understood that, still can modify or be equal to replacement the present invention, and not departing from any modification or partial replacement of the spirit and scope of the present invention, it all should be encompassed in claim scope of the present invention.
Claims (10)
1. from Potmarigold Calendula, prepare a method for high purity lutein ester, it is characterized in that: comprise the following steps:
A, get fresh Potmarigold Calendula, add extraction using alcohol, obtain extracting solution, then described extracting solution is concentrated, obtain concentrated solution;
B, described concentrated solution is added to the water of temperature≤10 ℃, mix, obtain suspension, then in this suspension, add charcoal absorption, filter, obtain filter residue;
C, described filter residue is placed in to chromatography column, with the mass percent concentration of temperature≤10 ℃, is first 60%～95% ethanolic soln wash-out, then uses acetone-ethanolic soln wash-out, collect elutriant, concentrated, obtain crude extract;
D, the acetone-dissolve with ethanol solution that is 10%～90% with mass percent concentration by described crude extract, crystallization, filters, dry, obtains.
2. a kind of method of preparing high purity lutein ester from Potmarigold Calendula according to claim 1, is characterized in that: in described step a, the add-on of ethanol is 2～10 times of weight of described Potmarigold Calendula weight.
3. a kind of method of preparing high purity lutein ester from Potmarigold Calendula according to claim 1, is characterized in that: the time of extracting in described step a is 1～3 hour, the temperature of extraction is 30 ℃～60 ℃, is extracted in vacuum condition and gets off to carry out.
4. a kind of method of preparing high purity lutein ester from Potmarigold Calendula according to claim 1, is characterized in that: in described step a, the volume of concentrated solution is described extracting liquid volume 1/3～1/5.
5. a kind of method of preparing high purity lutein ester from Potmarigold Calendula according to claim 1,, it is characterized in that: in described step b, the add-on of gac adds the gac of 1～10 weight part to carry out according to suspension described in every 100 parts by volume.
6. a kind of method of preparing high purity lutein ester from Potmarigold Calendula according to claim 5, is characterized in that: the number of times that described gac adds is 1～3 time.
7. a kind of method of preparing high purity lutein ester from Potmarigold Calendula according to claim 6, is characterized in that: at described gac, be added to after described suspension, stir 10～30min.
8. a kind of method of preparing high purity lutein ester from Potmarigold Calendula according to claim 1, is characterized in that: in described step c, the concentrated mode of concentrating under reduced pressure that adopts is carried out.
9. a kind of method of preparing high purity lutein ester from Potmarigold Calendula according to claim 1, is characterized in that: in described step a, before extraction using alcohol, also comprise oven dry, the step of pulverizing.
10. the lutein ester obtaining based on preparation method described in any one in claim 1-9.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105717056A (en) * | 2016-03-28 | 2016-06-29 | 内蒙古蒙牛乳业（集团）股份有限公司 | Method for measuring content of lutein dipalmitate in lutein ester product |
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| CN101759618A (en) * | 2008-12-25 | 2010-06-30 | 中国科学院兰州化学物理研究所 | Method for extracting lutein ester compounds form marigolds |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO1999020587A1 (en) * | 1997-10-21 | 1999-04-29 | Office Of Technology Liaison | Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants |
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| CN101759618A (en) * | 2008-12-25 | 2010-06-30 | 中国科学院兰州化学物理研究所 | Method for extracting lutein ester compounds form marigolds |
| CN101486671A (en) * | 2009-02-27 | 2009-07-22 | 大连医诺生物有限公司 | Preparation and stabilization of high-purity xanthophyll ester and method for removing pollutant thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105717056A (en) * | 2016-03-28 | 2016-06-29 | 内蒙古蒙牛乳业（集团）股份有限公司 | Method for measuring content of lutein dipalmitate in lutein ester product |
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