CN101130512A - Method for producing xanthophyll - Google Patents
Method for producing xanthophyll Download PDFInfo
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- CN101130512A CN101130512A CNA2007100185671A CN200710018567A CN101130512A CN 101130512 A CN101130512 A CN 101130512A CN A2007100185671 A CNA2007100185671 A CN A2007100185671A CN 200710018567 A CN200710018567 A CN 200710018567A CN 101130512 A CN101130512 A CN 101130512A
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Abstract
The invention discloses a method to extract, separate and purify natural pigment especially high purity lutein, which comprises the following steps: extracting patuletin; getting concrete; using as raw material; dissolving in mixed solvent of alcohol and tetrahydrofuran; adding into KOH water solution; heating the mixed liquid; saponifying; adding into deionized water; crystallizing; filtering; drying; getting lutein rough product; extracting with acetone; evaporating the acetone; leaching with alcohol; getting purified free state lutein. This invention possesses high purity, which is fit for raw material of food additive and medical health products.
Description
Technical field
The present invention relates to the method for a kind of natural pigment extraction, separation and purifying, particularly a kind of method for preparing food-grade high-purity xenthophylls.
Background technology
Xenthophylls (Lutein) has another name called " plant lutein ", is a kind of tetraterpenes natural pigment that extensively is present in the natural plant body, and this material belongs to carotenoid, is the main ingredient of plant pigmentss such as vegetables, fruit, flowers.According to foreign study, xenthophylls content in flowers such as deep green leaf vegetables such as wild cabbage, kale, spinach and marigold flower is the highest.Next is fruit such as pumpkin, peach, mango, citrus.This natural pigment has lovely luster, strong coloring force, safety non-toxic, advantage such as being rich in nutrition, now has been widely used in every field such as food, makeup, medicine, tobacco, bird feed.This compound is again a kind of antioxidant of excellent performance simultaneously, can resist oxyradical and cause cell and organ damage in human body, cardiovascula arteriosclerosis, coronary heart disease and tumor disease that the prevention body aging causes.In addition, xenthophylls still is the main carotenoid antioxidant component in the eye tissue retina, vision degeneration and the blind disease that can prevent senile eyeball macula retinae to degenerate and cause.
Because above these advantages and high nutritive value, FDA is just ratified xenthophylls as far back as nineteen ninety-five and is used for food and drink as food supplement.
3 chiral centres are arranged in the structure of xenthophylls, have 8 kinds of chiral isomers (in fact only there is a kind of isomer in nature).Studies show that to have only the xenthophylls ability biologically active in the natural phant such as kale, marigold flower.Aspect organic synthesis, since complex process, the cost height, the synthetic not success as yet so far of individual isomer xenthophylls, therefore the production of xenthophylls mainly depends on plant extract at present.
There are many pieces of documents and patent report xenthophylls to extract and isolating method at present, as US 5382714, US5648564, US 6262284 etc.The part but these technology still come with some shortcomings in US 5382714, has been used the bigger organic solvent of toxicity such as methylene dichloride when recrystallization, the residual of this kind solvent will be limited its application in food and medicine.Adopt alkaline propylene glycol solution to carry out saponification among the US 5648564, though this method can improve the solvability of raw material, make saponification more complete, but because propylene glycol viscosity height, long, temperature high one whole saponification process of saponification reaction time was 70 ℃ of reactions 10 hours, and this can cause a large amount of xenthophylls degradeds or isomerization; And propylene glycol boiling point height, the propylene glycol in the waste liquid is not easy to be recycled, can pollute environment.Use the solvent of tetrahydrofuran (THF) among the US 6262284 as the extraction of raw material marigold flower particle, saponification and recrystallization, consumption is very big when especially slightly carrying with saponification, produce nearly 200～300L of the employed tetrahydrofuran (THF) of 1Kg xenthophylls, cost is very high, though so this method available, the production cost height, aftertreatment is time-consuming, and tetrahydrofuran (THF) corrodibility is strong, and the maintenance of the equipment expense is high, so be not suitable for carrying out suitability for industrialized production.In addition, most of patent all requires temperature to reach-15 ℃ when recrystallization, need to use large-scale refrigerating apparatus, and this not only can improve production cost, also can improve energy consumption, is not inconsistent with the direction of development in science and technology now.
In sum, prior art has following shortcoming:
1) used the bigger solvent of some toxicity in the production process, the residual product that can hinder of these solvents is in medicine and Application in Food Industry; 2) saponification process temperature height, time are long, and xenthophylls is degraded or isomerization in process of production, make the production cycle long, and product purity is low; 3) use of a large amount of tetrahydrofuran (THF)s increases substantially production cost, has reduced the competitiveness of product in market; 4) need large-scale refrigerating apparatus carry out recrystallization, not only increase production cost, also improved energy consumption, be not inconsistent with the direction of development in science and technology now.
Summary of the invention
The objective of the invention is in order to overcome existing method production cost height, need large-scale refrigerating apparatus, defectives such as the products therefrom isomer is many, the invention provides the method for a kind of extraction from the medicinal extract (also claiming marigold oil resin) that marigold flower extracts, separation and purification of xanthophylls, this method is a solvent with ethanol cheap and easy to get, acetone and a small amount of tetrahydrofuran (THF), saponification and sepn process are easy, energy consumption is easy to realize industrialization for a short time, and extract the yield height, the product purity height need not use large-scale refrigerating apparatus.
Technical scheme of the present invention is, designs a kind of method for preparing xenthophylls, it is characterized in that: with the medicinal extract that extracts the Flower of Aztec Marigold gained is raw material, marigold extractum is dissolved in the mixed solvent of ethanol and tetrahydrofuran (THF), the KOH aqueous solution is added wherein, the heating mixed solution carries out saponification again, after saponification reaction is complete, add the deionized water crystallization, filter, get the xenthophylls crude product after the drying, use acetone extraction then, evaporation acetone is again with obtaining free xanthophyll after the ethanol drip washing.
Described saponification step is undertaken by following technology:
Marigold extractum is dissolved in the mixed solvent of 2.0～2.5 times of volume of ethanol of its weight and tetrahydrofuran (THF); Simultaneously that the KOH of 0.15～0.20 times of medicinal extract weight is soluble in water, be mixed with the KOH aqueous solution of weight percentage; Slowly add this basic solution in the above-mentioned mixed solvent system subsequently, 60～65 ℃ of following saponification 1～2 hour, the deionized water that the back adding marigold extractum that reacts completely weight is 2～2.2 times, continue to stir 30 minutes, treat that lutein crystal is complete, more after filtration, to obtain lutein content be xenthophylls crude product more than 70% to drying.
The proportioning of the mixed solvent of described ethanol and tetrahydrofuran (THF) is an ethanol: tetrahydrofuran (THF)=6.5～5.5: 0.8～1.2.
Described method for saponification is that marigold extractum is dissolved in 2.0～2.5 times of volume of ethanol and the tetrahydrofuran (THF) mixed solvent, add the KOH aqueous solution, and, add the deionized water of 2 times of marigold extractum weight again 60～65 ℃ of saponification 1～2 hour, after filtration, drying obtains crude product.
The consumption of described KOH is 0.15～0.20 times of marigold extractum weight, and KOH is water-soluble, and to be mixed with weight percentage be 14%～18% the KOH aqueous solution.
Described purification step is undertaken by following technology:
With above-mentioned saponification resultant by every gram add 280～320ml volume acetone solution, solvent temperature is 48～52 ℃, filtered while hot is removed insolubles; Gained filtrate after 50～55 ℃ of following vacuum boil off solvent, is used ethanol drip washing again, and drying obtains elaboration xenthophylls.
Characteristics of the present invention are:
In the mixed solvent of ethanol and a spot of tetrahydrofuran (THF), carry out saponification reaction, so both improved the solubleness of marigold extractum in solvent, avoided using the bigger propylene glycol of viscosity again.
It only is 3.4～3.6L that the present invention produces the employed tetrahydrofuran (THF) of 1Kg xenthophylls, the use of a spot of tetrahydrofuran (THF), cost impact is little, but improved the solubleness of marigold extractum in mixed solvent, shorten the saponification reaction time, avoided the xenthophylls degraded and the isomerization that cause because of the saponification reaction time.
The present invention is that the medicinal extract with dried marigold flower is dissolved in earlier in the mixing solutions of ethanol and tetrahydrofuran (THF), simultaneously that KOH is soluble in water, then these two kinds of solution are slowly mixed, under 60～65 ℃, carry out saponification, can make medicinal extract and KOH fully to be dissolved in the reaction system fast reaction speed apace like this.Directly in system, add deionized water after saponification reaction is complete, continue to stir 30 minutes, make that like this lutein crystal is complete, and crystal is bigger, is beneficial to filtration.
And under the situation of not using tetrahydrofuran (THF), use ethanol and water to be the saponification mixed solvent, and be unfavorable for the dissolving of medicinal extract, slow down the saponified speed of response, cause the xenthophylls yield to reduce; And because the micelle that generates is insoluble in this system, make filtering process speed slow, influenced the production cycle, also cause the finished product content can not reach 90% simultaneously, example 1 sees reference.
Crude product is purified a step, adopts acetone extraction, and the method for ethanol drip washing, this method can be removed the impurity that is insoluble to solvent and the degraded product of some xenthophylls, and only contain a spot of water (water content is lower than 2%) in the system, is beneficial to the recovery of acetone and recycles.Use the yield of this method purification xenthophylls and the basically identical as a result of purity and use mixed solvent recrystallization, and avoid moving large-scale refrigerating apparatus and use the bigger solvent of toxicity.U.S. Pat 5382714 uses methylene dichloride and normal hexane to get mixed solvent recrystallization 2～3 hours under-10～-20 ℃ of low temperature, not only need large-scale refrigerator, and crystallization time is long, and example 2 sees reference.
The free lutein purity of using the method for the invention production is more than 95%, the xenthophylls total recovery is more than 80%, be a kind of food grade high-content lutein, its impurity is based on zeaxanthin and some other carotenoid, can be used as Medicines and Health Product raw material, foodstuff additive safely and effectively.
Embodiment
Below further set forth the present invention, but following embodiment does not do any restriction to scope of the present invention, in this embodiment, the purity of xenthophylls is through high performance liquid chromatography (HPLC) assay determination, but the purity of being measured is not represented the qualification according to the resulting Reinheitszahl of the present invention.
(HPLC condition)
Chromatographic column: Aglient ZORBAX C18 post (150mm * 4.6mm, 5 μ m); Column temperature: 30 ℃;
Moving phase: acetonitrile-methyl alcohol (95: 5); Flow velocity: 1.0mL/min; Detect wavelength: 447nm.
To extract the resulting medicinal extract of Flower of Aztec Marigold is starting raw material, obtains content through saponification, after purifying greater than 95% free xanthophyll.This routine employed raw material marigold extractum is-solid or the thick liquid of kind of similar yellow or brown, it is corolla with dry feverfew Flower of Aztec Marigold (the es erecta. of Taget), after fermentation, dehydration, drying, pulverizing, make the normal hexane or the normal butane extract of marigold particles, it is marigold extractum (also claiming marigold oil resin), its main component is a lutein ester, is the commercially available prod.
Saponification step of the present invention is undertaken by following technology:
Marigold extractum is dissolved in the mixed solvent of 2.0～2.5 times of volume of ethanol and tetrahydrofuran (THF); Simultaneously that the KOH of 0.15～0.20 times of medicinal extract weight is soluble in water, be mixed with weight percentage and be 14%～18% the KOH aqueous solution.Subsequently this basic solution is slowly added in the above-mentioned mixed solvent system.Wherein the mixed solvent proportioning is an ethanol: tetrahydrofuran (THF)=6.5～5.5: 0.8～1.2, and consumption is 2.0～2.5 times of volumes of medicinal extract.Above-mentioned mixing solutions is heated to 60～65 ℃, saponification 1～2 hour, the back that reacts completely adds the deionized water of 2～2.2 times of marigold extractum weight, continues to stir 30 minutes, treat that lutein crystal is complete, more after filtration, to obtain lutein content be xenthophylls crude product more than 70% to drying.
Purification step of the present invention is undertaken by following technology:
With the volume ratio acetone solution of above-mentioned saponification resultant by every gram 280～320ml, it is mainly decided according to the content of xenthophylls in the crude product, with solvent temperature is 48～52 ℃, remove by filter impurity, after boiling off solvent, re-use ethanol drip washing and obtain pure product xenthophylls (content is higher than 95%), this technology is without recrystallization, so avoided the use of large-scale refrigerating apparatus.The conventional method that the method for using ethanol drip washing is adopted as the drip washing technology of this area.
The proportioning of saponification mixed solvent is an ethanol: tetrahydrofuran (THF)=6.5～5.5: 0.8～1.2.
The consumption of described KOH accounts for 0.15～0.2 times of marigold extractum weight, and the water-soluble quality percentage composition that is mixed with is 14%～18% the KOH aqueous solution.
Embodiment 1
With marigold extractum 130g (lutein content 10.1%), the mixed solvent of 270ml ethanol and tetrahydrofuran (THF), wherein ethanol: tetrahydrofuran (THF) is 6: 1 a ratio, add successively in the 1000ml there-necked flask, dissolving, and be heated to 50 ℃, continue to stir 10 minutes, dissolve fully up to medicinal extract.Get 26.0gKOH and be dissolved in the 120ml water, this solution is slowly poured in the there-necked flask, stir.Heating mixed solution to 65 degree centigrade reacted 1.5 hours.Stop heating, add the 260ml deionized water simultaneously again in there-necked flask, continue to stir 30 minutes, filter then, 50 ℃ of following vacuum-dryings 2 hours, obtain the orange-yellow crude product of 15.6g again, lutein content reaches 75.5%.The xenthophylls yield is 89.7%.
Get 10.0g xenthophylls crude product, add 2.5L acetone, be heated to 50 ℃ of dissolvings, the washing with acetone insolubles of 0.5L heat is used in heat filter while hot again, becomes pale brown look until the color of residue, remove this insolubles, merge acetone soln, at 50--55 ℃, use and concentrate withdrawer, vacuum condition is used ethanol drip washing, more then 50 ℃ of vacuum-dryings 8 hours after removing down and desolvating, get 7.3g red-purple pulverulent solids, wherein its content of xenthophylls is 97.0%.
The xenthophylls total recovery is 84.1%.
Embodiment 2
Adopt the raw material identical with embodiment 1, identical solvent load joins in the 1000ml there-necked flask and dissolves, and is heated to 50 ℃, continues stirring 10 minutes, dissolves fully up to medicinal extract.Get 26.0gKOH and be dissolved in the 120ml water, this solution is slowly poured in the there-necked flask, stir.Heating mixed solution to 60 ℃ reacted 1.5 hours.Stop heating, add the 260ml deionized water more again in there-necked flask, continue to stir 30 minutes, filter then, and vacuum-drying below 50 ℃ 2 hours, obtain the orange-yellow crude product of 15.5g, lutein content reaches 74.7%.60 ℃ of saponification temperatures, xenthophylls yield are 88.2%.
Get 10.0g xenthophylls crude product, add 2.5L acetone, be heated to 50 ℃ after, the washing with acetone insolubles of 0.5L heat is used in heat filter while hot again, becomes pale brown look until the color of residue, remove this insolubles, merge acetone soln,, use to concentrate withdrawer at 50--55 ℃, after vacuum condition removes down and desolvates, 50 ℃ of following vacuum-dryings 8 hours, get 7.2g red-purple pulverulent solids, wherein lutein content is 96.2%.
The xenthophylls total recovery is 82.2%.
Embodiment 3
Adopt the raw material identical with embodiment 1, the proportioning of saponified mixed solvent is an ethanol: tetrahydrofuran (THF)=5.5: 1.2.With marigold extractum 130g, the 270ml mixed solvent joins successively in the 1000ml there-necked flask and dissolves, and is heated to 50 ℃, continues to stir 10 minutes, dissolves fully up to medicinal extract.Other gets 26.0gKOH and is dissolved in the 120ml water, this solution is slowly poured in the there-necked flask again, stirs, and is heated to 65 ℃, reacts 1.5 hours.Stop heating, add the 260ml deionized water simultaneously again in there-necked flask, continue to stir 30 minutes, filter then, 50 ℃ of following vacuum-dryings 2 hours, obtain the orange-yellow crude product of 15.7g, lutein content reaches 74.5%.The xenthophylls yield is 89.0%.The ratio of tetrahydrofuran (THF) increases in the above-mentioned mixed solvent, but xenthophylls yield and purity do not have considerable change.
Get 10.0g xenthophylls crude product, add 2.5L acetone, be heated to 50 ℃, the washing with acetone insolubles of 0.5L heat is used in heat filter while hot again, becomes pale brown look until the color of residue, remove this insolubles, merge acetone soln, at 50--55 ℃, use and concentrate withdrawer, vacuum condition is used ethanol drip washing, more again 50 ℃ of vacuum-dryings 8 hours after removing down and desolvating, get 7.2g red-purple pulverulent solids, wherein its content of xenthophylls reaches 96.0%.
The xenthophylls total recovery is 83.5%.
Embodiment 4
Adopt the raw material identical with embodiment 1, the proportioning of saponified mixed solvent is an ethanol: tetrahydrofuran (THF)=6.5: 0.8.With marigold extractum 130g, the 280ml mixed solvent joins successively in the 1000ml there-necked flask and dissolves, and is heated to 50 ℃, continues to stir 10 minutes, dissolves fully up to medicinal extract.Get 26.0gKOH and be dissolved in the 120ml water, this solution is slowly poured in the there-necked flask, stir, be heated to 65 ℃, reacted 1.5 hours.Stop heating, add the 260ml deionized water simultaneously again in there-necked flask, continue to stir 30 minutes, filter then, 50 ℃ of following vacuum-dryings 2 hours, obtain the orange-yellow crude product of 15.8g, lutein content reaches 72.2%.The xenthophylls yield is 86.9%, and the ratio of tetrahydrofuran (THF) reduces in the mixed solvent, and xenthophylls yield and purity lower.
Get 10.0g xenthophylls crude product, add 2.5L acetone, be heated to 50 ℃, the washing with acetone insolubles of 0.5L heat is used in heat filter while hot again, becomes pale brown look until the color of residue, remove this insolubles, merge acetone soln, at 50--55 ℃, use and concentrate withdrawer, vacuum condition is used ethanol drip washing, more again 50 ℃ of vacuum-dryings 8 hours after removing down and desolvating, get 7.0g red-purple pulverulent solids, wherein its content of xenthophylls reaches 95.4%.
The xenthophylls total recovery is 80.5%.
Embodiment 5
Adopt the raw material identical with embodiment 1, same mixture solvent and working method, the saponification reaction time is 2 hours, obtains the orange-yellow crude product of 15.7g after the processing, and lutein content reaches 74.9%, and present embodiment xenthophylls yield is 89.5%.Purification treating method is with embodiment 1, and this method xenthophylls total recovery is 83.9%.The saponification reaction time lengthening, gained xenthophylls yield and purity and embodiment 1 do not have obviously difference.
Reference example 1
Adopt the raw material identical with embodiment 1, do not add tetrahydrofuran (THF) during saponification, all the other are operated by the method for embodiment 1, with the medicinal extract 130g of dried marigold flower, 270ml ethanol joins successively in the 1000ml there-necked flask and dissolves, be heated to 50 ℃, continue to stir 20 minutes.Get 26gKOH and be dissolved in the 120ml water, this solution is slowly poured in the there-necked flask, stir, be heated to 65 ℃, reacted 1.5 hours.Stop heating, add simultaneously the 260ml deionized water again in there-necked flask, continue to stir 30 minutes after-filtration, 50 ℃ of following vacuum-drying 2 hours obtains the orange-yellow crude product of 15.1g (lutein content 67.5%).Add in the absence of tetrahydrofuran (THF),, make filtering process speed slow, influenced the production cycle, also cause the finished product content can not reach 90% simultaneously because the micelle that generates is insoluble in this system.
Get 10.0g xenthophylls crude product, add 2.5L acetone, after being heated to 50 ℃, heat is filtered while hot, uses the washing with acetone insolubles of 0.5L heat again, color until residue becomes pale brown look, remove this insolubles, merge acetone soln, boil off solvent after, the red-purple pulverulent solids vacuum-drying of gained 8 hours gets 6.9g xenthophylls (content 88.1%).
The xenthophylls total recovery is 69.9%.
Reference example 2
Embodiment 1 gained xenthophylls crude product (content 75.5%) 2.0g is placed the mixed solvent of 30ml methylene dichloride and 30ml normal hexane, reflux 20 minutes, filtered while hot, with clear liquid at-15 ℃ of recrystallizations, the crystal of gained is again with 10ml normal hexane washing 2 times, vacuum-drying then 8 hours gets 1.4g xenthophylls (content 94.5%).
The xenthophylls total recovery is 78.5%.
Practical in industry
The present invention is made up of foregoing, from the angle of industrialization and business efficiency, is a kind of good production energy that has The new method of power, it obtains the free xanthophyll of high-load in a kind of simple and effective mode.
Claims (6)
1. method for preparing xenthophylls, it is characterized in that: the medicinal extract with extraction Flower of Aztec Marigold gained is raw material, marigold extractum is dissolved in the mixed solvent of ethanol and tetrahydrofuran (THF), the KOH aqueous solution is added wherein again, the heating mixed solution carries out saponification, after saponification reaction is complete, add the deionized water crystallization, filter, get the xenthophylls crude product after the drying, use acetone extraction then, evaporation acetone is again with the free xanthophyll after obtaining purifying after the ethanol drip washing.
2. a kind of method for preparing xenthophylls according to claim 1, it is characterized in that: described saponification step is undertaken by following technology:
Marigold extractum is dissolved in the mixed solvent of 2.0～2.5 times of volume of ethanol of its weight and tetrahydrofuran (THF); Simultaneously that the KOH of 0.15～0.20 times of medicinal extract weight is soluble in water, be mixed with the KOH aqueous solution of weight percentage; Slowly add this basic solution in the above-mentioned mixed solvent system subsequently, 60～65 ℃ of following saponification 1～2 hour, the deionized water that the back adding marigold extractum that reacts completely weight is 2～2.2 times, continue to stir 30 minutes, treat that lutein crystal is complete, more after filtration, to obtain lutein content be xenthophylls crude product more than 70% to drying.
3. a kind of method for preparing xenthophylls according to claim 1 is characterized in that: the proportioning of the mixed solvent of described ethanol and tetrahydrofuran (THF) is an ethanol: tetrahydrofuran (THF)=6.5～5.5: 0.8～1.2.
4. a kind of method for preparing xenthophylls according to claim 1, it is characterized in that: described method for saponification is that marigold extractum is dissolved in 2.0～2.5 times of volume of ethanol and the tetrahydrofuran (THF) mixed solvent, add the KOH aqueous solution, and 60～65 ℃ of saponification 1～2 hour, the deionized water that adds 2 times of marigold extractum weight again, after filtration, drying obtains crude product.
5. a kind of method for preparing xenthophylls according to claim 1 is characterized in that: the consumption of described KOH is 0.15～0.20 times of marigold extractum weight, and KOH is water-soluble, and to be mixed with weight percentage be 14%～18% the KOH aqueous solution.
6. a kind of method for preparing xenthophylls according to claim 1, it is characterized in that: described purification step is undertaken by following technology:
With the acetone solution of above-mentioned saponification resultant by every gram adding 280～320ml volume, solvent temperature is 48～52 ℃, and filtered while hot is removed insolubles; Gained filtrate after 50～55 ℃ of following vacuum boil off solvent, is used ethanol drip washing again, and drying obtains elaboration xenthophylls.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101979377A (en) * | 2010-09-20 | 2011-02-23 | 广州智特奇生物科技有限公司 | Method for saponifying lutein grease |
| CN101828693B (en) * | 2009-03-09 | 2013-01-02 | 浙江医药股份有限公司新昌制药厂 | Preparation method and application of low-viscosity high-fluidity carotenoid oil suspension |
| CN102887848A (en) * | 2012-10-30 | 2013-01-23 | 长沙芬康生物科技有限公司 | Method for preparing lutein crystals from marigold ointment by catalytic saponification |
| CN103319389A (en) * | 2013-06-28 | 2013-09-25 | 大连医诺生物有限公司 | Method for preparing food-grade lutein crystal from marigold extract |
| CN105646314A (en) * | 2015-12-30 | 2016-06-08 | 中国农业科学院郑州果树研究所 | Method for one-step extraction and saponification of marigold lutein |
| CN106316909A (en) * | 2016-08-19 | 2017-01-11 | 晨光生物科技集团股份有限公司 | Continuous lutein extract saponifying process |
| CN113563735A (en) * | 2021-08-25 | 2021-10-29 | 邯郸学院 | Dye for dye-sensitized solar cell and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5382714A (en) * | 1994-03-17 | 1995-01-17 | The Catholic University Of America | Process for isolation, purification, and recrystallization of lutein from saponified marigold oleoresin and uses thereof |
| US5648564A (en) * | 1995-12-21 | 1997-07-15 | Kemin Industries, Inc. | Process for the formation, isolation and purification of comestible xanthophyll crystals 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 |
| CN1259309C (en) * | 2004-06-03 | 2006-06-14 | 成都枫澜科技有限公司 | Method for preparing lutein crystal from marigold extractive |
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2007
- 2007-08-31 CN CN2007100185671A patent/CN101130512B/en not_active Expired - Fee Related
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101828693B (en) * | 2009-03-09 | 2013-01-02 | 浙江医药股份有限公司新昌制药厂 | Preparation method and application of low-viscosity high-fluidity carotenoid oil suspension |
| CN101979377A (en) * | 2010-09-20 | 2011-02-23 | 广州智特奇生物科技有限公司 | Method for saponifying lutein grease |
| CN101979377B (en) * | 2010-09-20 | 2013-12-25 | 广州智特奇生物科技有限公司 | Method for saponifying lutein grease |
| CN102887848A (en) * | 2012-10-30 | 2013-01-23 | 长沙芬康生物科技有限公司 | Method for preparing lutein crystals from marigold ointment by catalytic saponification |
| CN103319389A (en) * | 2013-06-28 | 2013-09-25 | 大连医诺生物有限公司 | Method for preparing food-grade lutein crystal from marigold extract |
| CN105646314A (en) * | 2015-12-30 | 2016-06-08 | 中国农业科学院郑州果树研究所 | Method for one-step extraction and saponification of marigold lutein |
| CN106316909A (en) * | 2016-08-19 | 2017-01-11 | 晨光生物科技集团股份有限公司 | Continuous lutein extract saponifying process |
| CN113563735A (en) * | 2021-08-25 | 2021-10-29 | 邯郸学院 | Dye for dye-sensitized solar cell and preparation method thereof |
| CN113563735B (en) * | 2021-08-25 | 2023-12-08 | 邯郸学院 | Dye for dye sensitized solar cell and preparation method thereof |
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