CN103992256B - A kind of method preparing high-purity lutein ester from pot marigold - Google Patents
A kind of method preparing high-purity lutein ester from pot marigold Download PDFInfo
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- CN103992256B CN103992256B CN201410209053.4A CN201410209053A CN103992256B CN 103992256 B CN103992256 B CN 103992256B CN 201410209053 A CN201410209053 A CN 201410209053A CN 103992256 B CN103992256 B CN 103992256B
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- pot marigold
- lutein ester
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Abstract
The present invention relates to a kind of method preparing high-purity lutein ester from pot marigold, belong to food, health food and technical field of phytochemistry.The method comprises the following steps: a, take fresh pot marigold, adds alcohol extract, obtains extract, then concentrated by described extract, obtain concentrate；B, by described concentrate add temperature≤10 DEG C water, mixing, obtain suspension, then in this suspension add charcoal absorption, filter, obtain filter residue；C, described filter residue is placed in chromatographic column, is first 60%～95% ethanol solution wash-out with the mass percent concentration of temperature≤10 DEG C, then use acetone ethanol eluant solution, collect eluent, concentration, obtain CE；D, acetone ethanol solution that described CE mass percent concentration is 10%～90% is dissolved, crystallization, filter, be dried, to obtain final product.The invention has the beneficial effects as follows: method is easy and simple to handle, gained lutein ester purity is high.
Description
Technical field
The invention belongs to food, health food and technical field of phytochemistry, be specifically related to a kind of from pot marigold
The method of middle preparation high-purity lutein ester.
Background technology
Lutein belongs to the tetraterpenes compound of carotenoids, is widely present in the flower of plant, leaf, really
In reality and some algae bio.Research shows, lutein has coloring, anti-oxidant, eyeshield, anti-painstaking effort
Pipe disease and the several functions such as anticancer, be widely used in food, medicine, health products, cosmetics and cultivation
The fields such as industry.Pot marigold petal Lutein content is the abundantest, is the master of lutein plant extract in recent years
Originate.Plant Lutein is presented in lutein ester, because lutein ester must be through hydrolysis in human body
Just can be absorbed by the body for lutein, in existing lutein preparation technology, general employing lutein ester is alkali saponified
Method obtain free lutein.
In China market, lutein product purity is many below 90% at present, how to export as primary raw materials, no
External main flow pigment product market can be entered.The existing various technology of China are difficult to obtain high-purity lutein ester,
Can introduce a lot of impurity during extracting is common problem.Owing to these impurity does not removes before saponification process
Go, on the one hand affect saponification effect, on the other hand add the difficulty of follow-up lutein purifying process, and fall
Low yield.Therefore, how to obtain high-purity lutein ester and just become the industry pass obtaining high purity lutein
Key problem.
Lutein ester is many at present is extracted by solvent extraction, obtains free lutein after extract saponification,
Lutein crystal is obtained again through the operation such as extraction or recrystallization.Wherein:
The Chinese patent of Application No. 201210257183.6 discloses one and is prepared crystal by marigold flower particle
The method of lutein, it adds alkaline aqueous solution in marigold particles, carries out saponification；It is subsequently adding salt solution,
Filter after stirring, obtain filter cake；With the filter cake described in alkane solvents extraction, it is filtrated to get fat filter
Cake；This goes fat filter cake oxolane to extract, and is extracted liquid, and extract recrystallizes after washing with water, then
Fractional crystallization, be dried, obtain lutein crystal.It is loaded down with trivial details that this preparation method also exists technological operation, and solvent is used
The shortcomings such as amount is big, the time-consuming length of recrystallization.
The Chinese patent of Application No. 201310076600.1 disclose a kind of Food-grade high-content lutein ester and
Its preparation method, will in marigold extractum add C2-4 alcoholic solvent, under the conditions of 30～60 DEG C agitator treating 3～
6 hours or ultrasonically treated 1～2 hour, filter after being cooled to 30～50 DEG C, obtain filter cake I；In filter cake I
Add methyl alcohol or ethanol washs 1～3 time, filter, obtain filter cake II；Filter cake II drying removes solvent,
Lutein ester content is about about 80%.
In sum, the precondition preparing high purity lutein is to obtain highly purified lutein ester, finds
The lutein ester preparation method that technological operation is easy, solvent load is few, product purity is high, is to improve pot marigold
Plant resources utilization rate, realize the key issue of high purity lutein large-scale industrialized production.
Summary of the invention
It is an object of the invention to provide a kind of method preparing high-purity lutein ester from pot marigold, the method
Easy and simple to handle, gained lutein ester purity is high.
The technical solution used in the present invention is a kind of method preparing high-purity lutein ester from pot marigold,
Comprise the following steps:
A, take fresh pot marigold, add alcohol extract, obtain extract, then described extract is concentrated,
Obtain concentrate；
B, by described concentrate add temperature≤10 DEG C water, mixing, obtain suspension, then to this suspension
Middle addition charcoal absorption, filters, obtains filter residue；Wherein, the addition of water is 1/2-2 times of concentrate volume.
C, described filter residue is placed in chromatographic column, first with the mass percent concentration of temperature≤10 DEG C be 60%～
95% ethanol solution wash-out, then use acetone-ethanol eluant solution, collect eluent, concentrate, obtain CE；
Wherein, when using acetone-ethanol eluant solution, acetone-ethanol solution is by the acetone and 100 of 60～90 parts by volume
The ethanol of parts by volume, mixes.
D, acetone-ethanol solution that described CE mass percent concentration is 10%～90% is dissolved,
Crystallization, filters, and is dried, to obtain final product.
As preferably, in described step a, the addition of ethanol is 2～10 times of weight of described pot marigold weight.
Particularly preferred, the addition of ethanol is 3 times of described pot marigold weight, 4 times, 5 times, 6 times, 7 times,
8 times and 9 times.
As preferably, the time extracted in described step a is 1～3 hour, the temperature of extraction be 30 DEG C～
60 DEG C, it is extracted in vacuum condition and gets off to carry out.Particularly preferred, the time of extraction is 2 hours, extracts
Temperature be 40 DEG C and 50 DEG C.
As preferably, in described step a, the volume of concentrate is the 1/3～1/5 of described extracting liquid volume.
As preferably, in described step b, the addition of activated carbon adds according to suspension described in every 100 parts by volume
The activated carbon entering 1～10 weight portions is carried out.Particularly preferred, the addition of activated carbon is according to every 100 bodies
The long-pending described suspension of part adds 2 parts by weight of activated carbon, 3 parts by weight of activated carbon, 4 parts by weight of activated carbon, 5 weights
Amount part activated carbon, 6 parts by weight of activated carbon, 7 parts by weight of activated carbon, 8 parts by weight of activated carbon and 9 weight portions are lived
Property charcoal.
As preferably, the number of times that described activated carbon adds is 1～3 time.Particularly preferred, the addition of activated carbon
Number of times is 2 times.
As preferably, add to described suspension at described activated carbon, stir 10～30min.
As preferably, described step c concentrates and uses the mode of reduced pressure concentration to carry out.
As preferably, described step a also includes before alcohol extract the step dried, pulverize.
The present invention also provides for a kind of lutein ester obtained by above-mentioned preparation method, by percentage to the quality, is somebody's turn to do
Lutein ester comprises myristic acid palmitate 25%～35%, dipalmitate 25%～41%, two nutmegs
Acid esters 10%～28%, palmitate stearate 8%～19%.
The present invention uses pot marigold to be material, and rich in lutein ester in pot marigold, its lutein ester comprises Pork and beans
Cool acid palmitate, dipalmitate, two myristinates, palmitate stearate, distearate,
The compositions such as single nutmeg acid esters, monopalmitate and monostearate.
Lutein and ester thereof in pot marigold are the most sensitive to photo-thermal, easily occur in extracting preparation process
Convert, go bad.The present invention, by controlling the temperature during oxygen contacts with material and extracts in air, has
Solve to effect lutein ester conversion, rotten problem during extraction.Meanwhile, ethanol and non-petroleum are used
The low boiling point solvents such as ether, acetone, n-hexane, reduce the solvent loss in production process and explosion precaution,
Reduce production difficulty, save production cost.
The beneficial effects of the present invention is: the present invention utilizes the high-affinity of lutein ester and activated carbon, can be
Alcohol-water mixture is combined closely with activated carbon, thus realizes easy, quickly, effectively with most polar impurities
Separate；The present invention utilizes the impurity such as chlorophyll different from lutein ester adsorptivity on the activated carbon simultaneously, logical
Cross chromatography, most oil-soluble impurities can be removed, then remove a small amount of residual impurity by Crystallization Procedure,
Thus obtain highly purified lutein ester, for utilization and the preparation solution of high purity lutein product of lutein ester
Determine key issue.
Detailed description of the invention
For making those skilled in the art understand production technology and the technique effect of the present invention in detail, below with specifically
Production instance be further described application and the technique effect of the present invention.
Embodiment 1:
A, take fresh pot marigold 1kg, add the ethanol that mass percent concentration is 95% of 8 times of weight very
Extract 1 hour in 50 DEG C of heating under empty condition, filter, obtain extract, then described extract is carried out dense
Contracting, is concentrated into the 1/3 of extracting liquid volume, obtains concentrate.
B, described concentrate is added the water of temperature 10 DEG C, mixing, obtain suspension, then according to every 100 bodies
Long-pending part suspension adds the amount of 7 parts by weight of activated carbon, adds charcoal absorption, filter in this suspension,
Obtain filter residue；Wherein, the number of times that activated carbon adds is 3 times.Wherein, the addition of water is the 1 of concentrate volume
Times.
C, described filter residue is placed in chromatographic column, is first 60% with the mass percent concentration that temperature is 10 DEG C
Ethanol solution elutes, then uses acetone-ethanol eluant solution, follows the tracks of through TLC, collects target eluent, decompression
Concentrate, obtain CE；Wherein, acetone-ethanol solution is by the acetone of 80 parts by volume and the second of 100 parts by volume
Alcohol mixes.
D, acetone-ethanol solution that described CE mass percent concentration is 20% is dissolved, crystallization,
Filter, be dried, obtain 5.88g lutein ester.
After testing, the purity of this lutein ester is 99%, and its content comprising myristic acid palmitate is 35%,
Dipalmitate 30%, two myristinates 18%, palmitate stearate 15%.
Embodiment 2:
A, take fresh pot marigold 1kg, dry, be crushed to 60 mesh, add the mass percent of 10 times of weight
Concentration be 95% ethanol under vacuum in 30 DEG C heating extract 3 hours, filter, obtain extract, so
After described extract is concentrated, be concentrated into the 1/5 of extracting liquid volume, obtain concentrate.
B, described concentrate is added the water of temperature 8 DEG C, mixing, obtain suspension, then according to every 100 bodies
Long-pending part suspension adds the amount of 1 parts by weight of activated carbon, adds charcoal absorption, filter in this suspension,
Obtain filter residue；Wherein, the addition of water is 2 times of concentrate volume；The number of times that activated carbon adds is 3 times.
C, described filter residue is placed in chromatographic column, is first 95% with the mass percent concentration that temperature is 5 DEG C
Ethanol solution elutes, then uses acetone-ethanol eluant solution, follows the tracks of through TLC, collects target eluent, decompression
Concentrate, obtain CE；Wherein, acetone-ethanol solution is by the acetone of 60 parts by volume and the second of 100 parts by volume
Alcohol mixes.
D, acetone-ethanol solution that described CE mass percent concentration is 50% is dissolved, crystallization,
Filter, be dried, obtain 5.93g lutein ester.
After testing, the purity of this lutein ester is 98%, and its content comprising myristic acid palmitate is 25%,
Dipalmitate 38%, two myristinates 27%, palmitate stearate 8%.
Embodiment 3:
A, taking fresh pot marigold 1kg, dry, be crushed to 20 mesh, the mass percent adding 2 times of weight is dense
Degree be 90% ethanol extract 3 times in 50 DEG C of heating under vacuum, extract 2 hours every time, filter,
Obtain extract, then described extract is concentrated, be concentrated into the 1/4 of extracting liquid volume, obtain concentrate.
B, described concentrate is added the water of temperature 2 DEG C, mixing, obtain suspension, then according to every 100 bodies
Long-pending part suspension adds the amount of 10 parts by weight of activated carbon, adds charcoal absorption, filter in this suspension,
Obtain filter residue；Wherein, the addition of water is the 1/2 of concentrate volume；The number of times that activated carbon adds is 2 times.
C, described filter residue is placed in chromatographic column, is first 75% with the mass percent concentration that temperature is 2 DEG C
Ethanol solution elutes, then uses acetone-ethanol eluant solution, follows the tracks of through TLC, collects target eluent, decompression
Concentrate, obtain CE；Wherein, acetone-ethanol solution is by the acetone of 90 parts by volume and the second of 100 parts by volume
Alcohol mixes.
D, acetone-ethanol solution that described CE mass percent concentration is 90% is dissolved, crystallization,
Filter, be dried, obtain 6.03g lutein ester.
After testing, the purity of this lutein ester is 99%, and its content comprising myristic acid palmitate is 30%,
Dipalmitate 25%, two myristinates 25%, palmitate stearate 19%.
Embodiment 4:
A, take fresh pot marigold 1kg, dry, to the moisture of pot marigold less than 10%, be crushed to 40 mesh,
The ethanol that mass percent concentration is 85% adding 6 times of weight heats extraction 2 in 40 DEG C under vacuum
Secondary, extract 2 hours every time, filter, obtain extract, then described extract is concentrated, be concentrated into
The 1/3 of extracting liquid volume, obtains concentrate.
B, described concentrate is added the water of temperature 0 DEG C, mixing, obtain suspension, then according to every 100 bodies
Long-pending part suspension adds the amount of 4 parts by weight of activated carbon, adds charcoal absorption, filter in this suspension,
Obtain filter residue；Wherein, the addition of water is 1.5 times of concentrate volume；The number of times that activated carbon adds is 3 times.
C, described filter residue is placed in chromatographic column, is first 85% with the mass percent concentration that temperature is 2 DEG C
Ethanol solution elutes, then uses acetone-ethanol eluant solution, follows the tracks of through TLC, collects target eluent, decompression
Concentrate, obtain CE；Wherein, acetone-ethanol solution is by the acetone of 85 parts by volume and the second of 100 parts by volume
Alcohol mixes.
D, acetone-ethanol solution that described CE mass percent concentration is 90% is dissolved, crystallization,
Filter, be dried, obtain 6.11g lutein ester.
After testing, the purity of this lutein ester is 99%, and its content comprising myristic acid palmitate is 30%,
Dipalmitate 25%, two myristinates 25%, palmitate stearate 19%.
The purity of above-described embodiment gained lutein ester is high, and the component of composition is clear and definite, compares the leaf of existing preparation
Flavine ester has significant technological progress.
Finally it should be noted that above example, only in order to illustrative not limiting technical scheme, is use up
The present invention has been described in detail by pipe with reference to above-described embodiment, it will be appreciated by those skilled in the art that still
Can modify the present invention or equivalent, without departing from the spirit and scope of the present invention any repaiies
Changing or local is replaced, it all should be contained in scope of the presently claimed invention.
Claims (7)
1. the method preparing lutein ester from pot marigold, it is characterised in that: comprise the following steps:
A, take fresh pot marigold, add alcohol extract, obtain extract, then described extract is concentrated,
Obtain concentrate；
B, by described concentrate add temperature≤10 DEG C water, mixing, obtain suspension, then to this suspension
Middle addition charcoal absorption, filters, obtains filter residue；
C, described filter residue is placed in chromatographic column, first with the mass percent concentration of temperature≤10 DEG C be 60%～
95% ethanol solution wash-out, then use acetone-ethanol eluant solution, collect eluent, concentrate, obtain CE；
D, acetone-ethanol solution that described CE mass percent concentration is 10%～90% is dissolved,
Crystallization, filters, and is dried, to obtain final product；
In described step b, the addition of activated carbon adds 1～10 weights according to suspension described in every 100 parts by volume
The activated carbon of amount part is carried out；
The number of times that described activated carbon adds is 1～3 time.
A kind of method preparing lutein ester from pot marigold the most according to claim 1, its feature exists
In: in described step a, the addition of ethanol is 2～10 times of weight of described pot marigold weight.
A kind of method preparing lutein ester from pot marigold the most according to claim 1, its feature exists
In: the time extracted in described step a is 1～3 hour, and the temperature of extraction is 30 DEG C～60 DEG C, is extracted in
Vacuum condition gets off and carries out.
A kind of method preparing lutein ester from pot marigold the most according to claim 1, its feature exists
In: in described step a, the volume of concentrate is the 1/3～1/5 of described extracting liquid volume.
A kind of method preparing lutein ester from pot marigold the most according to claim 1, its feature exists
In: add to described suspension at described activated carbon, stir 10～30min.
A kind of method preparing lutein ester from pot marigold the most according to claim 1, its feature exists
In: described step c concentrates and uses the mode of reduced pressure concentration to carry out.
A kind of method preparing lutein ester from pot marigold the most according to claim 1, its feature exists
In: described step a also includes before alcohol extract the step dried, pulverize.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN1872839A (en) * | 2006-05-17 | 2006-12-06 | 浙江医药股份有限公司新昌制药厂 | Method for separating and purifying high-content lutein fatty acid ester from marigold oleoresin |
| 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 |
| 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 |
| 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 |
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- 2014-05-17 CN CN201410209053.4A patent/CN103992256B/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN1872839A (en) * | 2006-05-17 | 2006-12-06 | 浙江医药股份有限公司新昌制药厂 | Method for separating and purifying high-content lutein fatty acid ester from marigold oleoresin |
| 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 |
| 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 |
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