CN102796034A - Method for preparing lutein crystal from marigold flowers - Google Patents
Method for preparing lutein crystal from marigold flowers Download PDFInfo
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- CN102796034A CN102796034A CN2012102571836A CN201210257183A CN102796034A CN 102796034 A CN102796034 A CN 102796034A CN 2012102571836 A CN2012102571836 A CN 2012102571836A CN 201210257183 A CN201210257183 A CN 201210257183A CN 102796034 A CN102796034 A CN 102796034A
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Abstract
The invention discloses a method for preparing a lutein crystal from marigold flowers, and the method comprises the following steps of: adding an alkali aqueous solution to marigold flower particles to saponify; then adding saline water, uniformly stirring and filtering to obtain a filter cake; extracting the filter cake by using an alkane solvent, and filtering to obtain a degreasing filter cake; extracting the degreasing filter cake by using tetrahydrofuran to obtain extract liquor; and washing the extract liquor with water, then recrystallizing, carrying out fractional crystallization, and drying to obtain the lutein crystal. According to the method, as the marigold flower particles are directly saponified by using the alkali aqueous solution, the production efficiency is beneficially improved; after the marigold flower particles are saponified, the generated saponin substances are removed by using the saline water, the phenomenon of wasting a large amount of lutein crystals in the traditional process when the saponin substances are removed is avoided; and due to the characteristics of small dissolvability of the lutein crystal in the alkane solvent, a lot of target substances are avoided from being taken away when the lutein crystal is purified in the conventional process, so that the extracting rate is effectively improved.
Description
Technical field
The present invention relates to a kind of preparation method of xenthophylls, especially a kind of method by marigold flower granules prepn crystal lutein.
Background technology
Xenthophylls belongs to the tetraterpenes compound of carotenoids; Extensively be present in flower, leaf, fruit and some algae bio of plant; Especially in the petal of Flower of Aztec Marigold, exist in a large number; Its existence form in plant is a lutein ester, and the alkaline saponified method of general employing obtains xenthophylls in the industry.Xenthophylls is orange to safran powder, and weak Radix Glycyrrhizae smell is arranged, and is soluble in organic solvents such as THF, chloroform, pimelinketone, and solubleness is very little in normal hexane.In recent years, the biological function of relevant xenthophylls more and more causes people's attention.Xenthophylls has stronger antioxygenation, can remove the objectionable impurities " radical " that produces in the physiological metabolism process in the human body, and this type of " radical " can cause pathologies such as tissue injury, cell aging.
Because the xenthophylls molecular structure is complicated, the synthetic relatively difficulty of industry, and the xenthophylls of phytosynthesis have advantages such as natural, toxicological harmless, and it are lower to extract refining cost, is easy to scale operation.The own one-tenth scale of production of present lutein resin, but the xenthophylls of being produced is the oleo-resinous form mostly, contains higher impurity component, relatively is suitable as animal-feed, but use in the human food prods as tinting material and supplementary, then lack security.
Chinese patent CN101429146A discloses and has a kind ofly prepared lutein crystal and working method thereof by marigold petal, and it adopts alkane as xenthophylls diester in the solvent extraction marigold petal, and extracting solution is through carry out saponification reaction behind the concentrating under reduced pressure again in the system that ethanol, NaOH form; Add water and get the xenthophylls coarse crystallization; The crystal bullion is used the halogenated alkane recrystallization, adds the ethanol molecular distillation and removes halogenated alkane, filters; Behind the drying under reduced pressure, obtain lutein crystal.There is length consuming time in this method, problems such as solvent-oil ratio is big, cost height.
Chinese patent CN1436774A discloses a kind of method for preparing lutein crystal from marigold flower; This method is at first extracted lutein ester with non-polar solvent from marigold flower under heating condition; Then under stirring and heating condition; With alkaline solution the lutein ester strong solution is carried out saponification, again with separation behind the vaal water dilution saponification reaction product, washing, vacuum-drying; After this gained lutein crystal is slowly being stirred recrystallization in THF/vaal water/normal hexane or sherwood oil three combination solvents down, suction filtration washs vacuum-drying again.This method exist extract that yield is low, saponification reaction time length, complex process, cost is high, solvent is difficult for recovery characteristics.
Summary of the invention
The technical problem that the present invention will solve provides the method by marigold flower granules prepn crystal lutein that a kind of technology is simple, extraction yield is high.
For solving the problems of the technologies described above, the technical scheme that the present invention taked is: it adds alkaline aqueous solution in the marigold flower particle, carries out saponification; Add salt solution then, the after-filtration that stirs obtains filter cake; Extract described filter cake with alkane solvents, filter and obtain the degrease filter cake; Described degrease filter cake extracts with THF, obtains extraction liquid; Described extraction liquid with water washing after recrystallization, fractional crystallization, drying promptly obtain lutein crystal again.
The mass percentage concentration of alkaline aqueous solution according to the invention is 40～50%, and the mass ratio of alkaline aqueous solution and marigold particles is 3～10:1; Said saponification temperature is 75～85 ℃, and saponification time is 4～6h.
Behind the adding salt solution according to the invention, stir at 75～85 ℃.Described salt solution is that mass percentage concentration is 2%～5% sodium chloride aqueous solution, and said salt solution and marigold flower particulate mass ratio are 3～10:1.
Alkane solvents of the present invention is at 30～40 ℃ of extraction filter cakes.Described alkane solvents is one or more mixing in normal hexane, Skellysolve A, the normal heptane, and alkane solvents is 3～6:1 (ml/g) with the ratio of filter cake.
THF according to the invention is 4～6:1 (ml/g) with the ratio of degrease residue, 45～60 ℃ of extraction temperature.
Recrystallization of the present invention is: recrystallization was after described extraction liquid used water washing: described extraction liquid adds the deionized water of 0.5～1 times of its volume, at 35～55 ℃ of back standing demix that stir, keeps the solvent layer on upper strata; Above-mentioned solvent layer is concentrated, refrigerates, lutein crystal is separated out.Described solvent layer is concentrated into xenthophylls weight and accounts for 41～44% of gross weight.Described refrigerating temperature is 0～10 ℃, and cold preservation time is 6～12h; In the temperature-fall period, the control cooling rate is for per hour reducing by 5 ℃ before the refrigeration, and stirring velocity is lower than 6 rev/mins.
Adopt the beneficial effect that technique scheme produced to be: the present invention adopts the direct saponification marigold particles of alkaline aqueous solution; Do not add organic reagent in the saponification process; Avoided from marigold particles, extracting earlier in the traditional method lutein oleoresin (being dissolved in organic reagent) back resaponifying step, helped enhancing productivity.Utilize salt solution that the soap-like matter that generates is removed after the saponification of the present invention; Because of not using organic reagent in the saponification process; The crystal lutein of this moment also is kept in the plant materials, and the phenomenon of wasting a large amount of crystal luteins when having avoided removing soap-like matter in the traditional technology process takes place.The present invention utilizes the very little characteristic of crystal lutein solubleness in alkane solvents; Thereby before extracting xenthophylls with the raw material filter cake in other residual lipid-soluble substances remove the effect of playing purifying; Compare with common process; Take away a large amount of target substances when having avoided in the common process purified crystals xenthophylls, thereby improve extraction yield effectively.The present invention adopts THF to extract xenthophylls, utilizes the deionized water dilution to obtain the crystalline mode with common process and compares, have higher yield; Extracting solution is concentrated into to a certain degree post crystallization, adopts a step can obtain high-purity crystals xenthophylls, compare simpler with common process purified crystals step.
Embodiment
Below in conjunction with specific embodiment the present invention is done further detailed explanation.
Embodiment 1: the process step by the method for marigold flower granules prepn crystal lutein is described below.
Take by weighing the marigold particles of 50g total carotinoid content 1.83wt%, to the potassium hydroxide aqueous solution that wherein adds 150g, 40wt%, 80 ℃ of insulated and stirred, saponification reaction were carried out 5 hours.To the sodium chloride aqueous solution that wherein adds 300g, 2wt%, be heated to 80 ℃ of after-filtration that stir after saponification is accomplished, obtain filter cake.In filter cake, add the normal hexane solvent and under 40 ℃ of conditions, extract fat-soluble component wherein, every gram filter cake adds normal hexane solvent 5ml, filters and obtains the degrease filter cake.In the degrease filter cake, add tetrahydrofuran solvent, extraction is 2 times under 50 ℃ of conditions, and every gram degrease filter cake adds tetrahydrofuran solvent 5ml altogether, obtains containing the THF extraction liquid of xenthophylls; The deionized water that in extraction liquid, adds 0.75 times of its volume at 35 ℃ of back standing demix that stir, is collected upper strata THF layer; Concentrate tetrahydrofuran solvent layer to xenthophylls weight then and account for 42% of gross weight; Be to leave standstill 10 hours under 5 ℃ the condition in temperature, in the temperature-fall period, the control cooling rate is for per hour reducing by 5 ℃ before the refrigeration; Stirring velocity is lower than 6 rev/mins, filters to obtain lutein crystal; With lutein crystal vacuum-drying, obtain 0.84 gram crystal lutein.Detect through HPLC, total carotinoid content reaches 88.2wt% in the crystal lutein of gained, and alltrans xenthophylls purity is 80.88%, and the product yield is 80.97%.
Embodiment 2: the process step by the method for marigold flower granules prepn crystal lutein is described below.
Take by weighing the marigold particles of 50g total carotinoid content 1.94wt%, to the aqueous solution of the Pottasium Hydroxide that wherein adds 300g, 45wt%, 85 ℃ of insulated and stirred, saponification reaction were carried out 4.5 hours.To the sodium chloride solution that wherein adds 350g, 5wt%, be heated to 80 ℃ of after-filtration that stir after saponification is accomplished, obtain filter cake.In filter cake, add the Skellysolve A solvent and under 35 ℃ of conditions, extract fat-soluble component wherein, every gram filter cake adds Skellysolve A solvent 4ml, filters and obtains the degrease filter cake.The tetrahydrofuran solvent that in the degrease filter cake, adds, extraction is 2 times under 55 ℃ of conditions, and every gram degrease filter cake adds tetrahydrofuran solvent 4ml altogether, obtains containing the THF extraction liquid of xenthophylls; The deionized water that in extraction liquid, adds its 1 times of volume at 45 ℃ of back standing demix that stir, is collected upper strata THF layer; Concentrate tetrahydrofuran solvent layer to xenthophylls weight then and account for 44% of gross weight; Be to leave standstill 12 hours under 8 ℃ the condition in temperature, in the temperature-fall period, the control cooling rate is for per hour reducing by 5 ℃ before the refrigeration; Stirring velocity is lower than 6 rev/mins; Filtration obtains lutein crystal, with crystal vacuum-drying, obtains 0.873 gram crystal lutein.Detect through HPLC, total carotinoid content reaches 90.3wt% in the crystal lutein of gained, and alltrans xenthophylls purity is 83.07%, and the product yield is 81.27%.
Embodiment 3: the process step by the method for marigold flower granules prepn crystal lutein is described below.
Take by weighing the marigold particles of 100g total carotinoid content 1.90wt%, to the potassium hydroxide aqueous solution that wherein adds 800g, 50wt%, 75 ℃ of insulated and stirred, saponification reaction were carried out 6 hours.To the sodium chloride aqueous solution that wherein adds 300g, 4wt%, be heated to 85 ℃ of after-filtration that stir after saponification is accomplished, obtain filter cake.In filter cake, add normal heptane solvent and under 30 ℃ of conditions, extract fat-soluble component wherein, every gram filter cake adds normal hexane solvent 6ml, filters and obtains the degrease filter cake.In the degrease filter cake, add tetrahydrofuran solvent, extract under 60 ℃ of conditions, every gram degrease filter cake adds tetrahydrofuran solvent 6ml altogether, obtains containing the THF extraction liquid of xenthophylls; The deionized water that in extraction liquid, adds 0.5 times of its volume at 55 ℃ of back standing demix that stir, is collected upper strata THF layer; Concentrating tetrahydrofuran solvent layer to xenthophylls weight then and account for 43% of gross weight, is to leave standstill 6 hours under 0 ℃ the condition in temperature, filters and obtains lutein crystal; With lutein crystal vacuum-drying, obtain 1.7 gram crystal luteins.Detect through HPLC, total carotinoid content reaches 89.7wt% in the crystal lutein of gained, and alltrans xenthophylls purity is 81.34%, and the product yield is 80.26%.
Embodiment 4: the process step by the method for marigold flower granules prepn crystal lutein is described below.
Take by weighing the marigold particles of 50g total carotinoid content 1.87wt%, to the aqueous sodium hydroxide solution that wherein adds 500g, 45wt%, 77 ℃ of insulated and stirred, saponification reaction were carried out 4 hours.To the sodium chloride aqueous solution that wherein adds 200g, 3wt%, be heated to 75 ℃ of after-filtration that stir after saponification is accomplished, obtain filter cake.Adding normal hexane and Skellysolve A mixed solvent (volume ratio of normal hexane and Skellysolve A is 1:1) extract fat-soluble component wherein under 32 ℃ of conditions in filter cake, and every gram filter cake adds mixed solvent 3ml, filter and obtain the degrease filter cake.In the degrease filter cake, add tetrahydrofuran solvent, extraction is 2 times under 45 ℃ of conditions, and every gram degrease filter cake adds tetrahydrofuran solvent 4.5ml altogether, obtains containing the THF extraction liquid of xenthophylls; The deionized water that in extraction liquid, adds 0.8 times of its volume at 40 ℃ of back standing demix that stir, is collected upper strata THF layer; Concentrating tetrahydrofuran solvent layer to xenthophylls weight then and account for 41% of gross weight, is to leave standstill 8 hours under 10 ℃ the condition in temperature, filters and obtains lutein crystal; With lutein crystal vacuum-drying, obtain 0.86 gram crystal lutein.Detect through HPLC, total carotinoid content reaches 88.9wt% in the crystal lutein of gained, and alltrans xenthophylls purity is 82.48%, and the product yield is 81.77%.
Embodiment 5: the process step by the method for marigold flower granules prepn crystal lutein is described below.
Take by weighing the marigold particles of 50g total carotinoid content 1.92wt%, to the aqueous sodium hydroxide solution that wherein adds 250g, 45wt%, 82 ℃ of insulated and stirred, saponification reaction were carried out 5.5 hours.To the sodium chloride aqueous solution that wherein adds 500g, 3.5wt%, be heated to 80 ℃ of after-filtration that stir after saponification is accomplished, obtain filter cake.Adding normal hexane and normal heptane mixed solvent extract fat-soluble component wherein under 38 ℃ of conditions in filter cake, and every gram filter cake adds mixed solvent 4.5ml, filter and obtain the degrease filter cake.In the degrease filter cake, add tetrahydrofuran solvent, extract under 50 ℃ of conditions, every gram degrease filter cake adds tetrahydrofuran solvent 5.5ml altogether, obtains containing the THF extraction liquid of xenthophylls; The deionized water that in extraction liquid, adds 0.6 times of its volume at 50 ℃ of back standing demix that stir, is collected upper strata THF layer; Concentrate tetrahydrofuran solvent layer to xenthophylls weight then and account for 42.5% of gross weight; Be to leave standstill 9 hours under 3 ℃ the condition in temperature, in the temperature-fall period, the control cooling rate is for per hour reducing by 5 ℃ before the refrigeration; Stirring velocity is lower than 6 rev/mins, filters to obtain lutein crystal; With lutein crystal vacuum-drying, obtain 0.85 gram crystal lutein.Detect through HPLC, total carotinoid content reaches 90.1wt% in the crystal lutein of gained, and alltrans xenthophylls purity is 81.03%, and the product yield is 79.77%.
Claims (10)
1. method by marigold flower granules prepn crystal lutein, it is characterized in that: it adds alkaline aqueous solution in the marigold flower particle, carries out saponification; Add salt solution then, the after-filtration that stirs obtains filter cake; Extract described filter cake with alkane solvents, filter and obtain the degrease filter cake; Described degrease filter cake extracts with THF, obtains extraction liquid; Described extraction liquid with water washing after recrystallization, fractional crystallization, drying promptly obtain lutein crystal again.
2. the method by marigold flower granules prepn crystal lutein according to claim 1 is characterized in that: the mass percentage concentration of said alkaline aqueous solution is 40～50%, and the mass ratio of alkaline aqueous solution and marigold particles is 3～10:1; Said saponification temperature is 75～85 ℃, and saponification time is 4～6h.
3. the method by marigold flower granules prepn crystal lutein according to claim 1 is characterized in that: behind the said adding salt solution, stir at 75～85 ℃.
4. the method by marigold flower granules prepn crystal lutein according to claim 3 is characterized in that: described salt solution is that mass percentage concentration is 2%～5% sodium chloride aqueous solution, and said salt solution and marigold flower particulate mass ratio are 3～10:1.
5. the method by marigold flower granules prepn crystal lutein according to claim 1 is characterized in that: described alkane solvents is at 30～40 ℃ of extraction filter cakes.
6. the method by marigold flower granules prepn crystal lutein according to claim 5; It is characterized in that: described alkane solvents is one or more mixing in normal hexane, Skellysolve A, the normal heptane, and alkane solvents is 3～6:1 (ml/g) with the ratio of filter cake.
7. the method by marigold flower granules prepn crystal lutein according to claim 1 is characterized in that: said THF is 4～6:1 (ml/g) with the ratio of degrease residue, 45～60 ℃ of extraction temperature.
8. according to described any one the method for claim 1-7 by marigold flower granules prepn crystal lutein; It is characterized in that; Recrystallization was after described extraction liquid used water washing: described extraction liquid adds the deionized water of 0.5～1 times of its volume; At 35～55 ℃ of back standing demix that stir, keep the solvent layer on upper strata; Above-mentioned solvent layer is concentrated, refrigerates, lutein crystal is separated out.
9. the method by marigold flower granules prepn crystal lutein according to claim 8 is characterized in that: described solvent layer is concentrated into xenthophylls weight and accounts for 41～44% of gross weight.
10. a kind of method by marigold flower granules prepn crystal lutein according to claim 8 is characterized in that: described refrigerating temperature is 0～10 ℃, and cold preservation time is 6～12h; In the temperature-fall period, the control cooling rate is for per hour reducing by 5 ℃ before the refrigeration, and stirring velocity is lower than 6 rev/mins.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107242565A (en) * | 2017-05-27 | 2017-10-13 | 新疆红帆生物科技有限公司 | Marigold is health food xanthophyll soft capsule of raw material and preparation method thereof |
| CN108008036A (en) * | 2017-11-23 | 2018-05-08 | 广州市辉乐医药科技有限公司 | A kind of method for measuring Flos Tagetis Erectae extract Lutein content |
| WO2020073976A1 (en) * | 2018-10-12 | 2020-04-16 | 晨光生物科技集团股份有限公司 | Industrial preparation method of lutein and marigold flavone |
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Cited By (3)
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| CN107242565A (en) * | 2017-05-27 | 2017-10-13 | 新疆红帆生物科技有限公司 | Marigold is health food xanthophyll soft capsule of raw material and preparation method thereof |
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| WO2020073976A1 (en) * | 2018-10-12 | 2020-04-16 | 晨光生物科技集团股份有限公司 | Industrial preparation method of lutein and marigold flavone |
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