CN110003071A - A kind of industrial method quickly and efficiently extracting lutein and quercetagetin - Google Patents
A kind of industrial method quickly and efficiently extracting lutein and quercetagetin Download PDFInfo
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- CN110003071A CN110003071A CN201910397773.0A CN201910397773A CN110003071A CN 110003071 A CN110003071 A CN 110003071A CN 201910397773 A CN201910397773 A CN 201910397773A CN 110003071 A CN110003071 A CN 110003071A
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- hexane
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
The present invention relates to field of natural product extraction, more particularly to a kind of industrial method for quickly and efficiently extracting lutein and quercetagetin, its main improvements is, marigold flower particle is extracted using the mixed liquor of n-hexane and acetone soln as extractant, the volume fraction of acetone is 80~100% in the acetone soln.Mixing extractant of the invention has very high selectivity to lutein and quercetagetin, effectively above two effective component can be extracted, subsequent process is easily separated the quercetagetin product that lutein and high-purity can be obtained, simple process, production cost is low, is conducive to industrialized production.
Description
Technical field
The invention belongs to the extraction fields of natural constituent, and in particular to one kind from marigold flower extract lutein and
The method of quercetagetin.
Background technique
Contain rich functionality ingredient in marigold, there are many wherein flavonoids contains, such as quercetagetin, 6- hydroxyl mountain
How the flavone components such as phenol and patuletin, there are also the ingredients such as some amino acid.In addition, lutein also rich in marigold
Deng.Extracting method about lutein and flavones at present mainly uses step by step arithmetic method, i.e., it is yellow to extract leaf first with n-hexane
Then element obtains flavonoids product using the solvent processing marigold flower dregs of rice.In addition having two patents is extracted using mixed solvent,
As used aqueous two-phase solvent to extract in Chinese patent 201410104645.X；Mainly extraction obtains lutein and flavones is mixed
Close object.Chinese patent 201811188771.2 is extracted using the mixed solvent of petroleum ether and acetone, is selected in the patent
Separate mode be added water after separated, complicated operation, and can not isolated high-purity quercitrin marigold
Marigold flavone mixture only can be obtained in element.It is mainly sharp about the preparation method of high-purity quercetagetin in the prior art
Use chromatographic isolation.As Chinese patent CN201410708334.4 is disclosed through one-dimensional liquid chromatogram and the extraction of two-dimensional liquid chromatography method
Obtain the quercetagetin of high-purity.Chinese patent 201610108596.6 is by the side such as being centrifuged repeatedly, being filtered, washed
Method is prepared the quercetagetin that content is greater than 85%, yet there are no and purify to obtain the quercitrin of high-content by simple separation
The related report of patuletin.
Summary of the invention
The present invention relates to a kind of step is simple, the industrialization side of lutein and quercetagetin can be quickly and efficiently extracted
Method, main improvements are to mention using the mixed liquor of n-hexane and acetone soln as extractant to marigold flower particle
It takes, the volume fraction of acetone is 80~100% in the acetone soln.
Marigold flower particle is extracted using the mixed solution of 80~100% acetone of above-mentioned n-hexane and concentration, is mentioned
The main component obtained is lutein and quercetagetin ingredient, acetone concentration of the other impurities ingredient in this range
It is seldom suggested down, the quercetagetin and lutein of high-purity can be obtained by subsequent simply isolate and purify.
Preferably, the volume ratio of the n-hexane and the acetone soln is less than 1:3.The usage ratio of n-hexane and acetone
There is important influence to the extraction of quercetagetin, under this ratio, ten thousand longevity of quercitrin for being more advantageous in marigold flower particle
Chrysanthemum element is fully extracted out.
It is further preferred that the volume ratio of the n-hexane and the acetone soln is 1:3~5.Under this preferred proportion,
Not only it is close complete to have can guarantee that the quercetagetin in marigold flower particle was extracted, but also can effectively save solvent consumption and production
Cost.
Preferably, the mass volume ratio of the marigold flower particle and the extractant is less than 1:4, under this ratio, more
The lutein and quercetagetin be conducive in marigold flower particle is fully extracted.
It is further preferred that mass volume ratio is 1:4~7.Under this preferred proportion, both it can guarantee in marigold flower particle
Lutein and quercetagetin be extracted as much as possible completely, and can effectively save solvent consumption and production cost.
Preferably, Extracting temperature is 20~55 DEG C, extraction time 2-8h.
Preferably, the concrete operations of the extraction can be the extracting methods commonly used in the art such as extraction, adverse current extraction.
Preferably, being evaporated to the extracting solution dissolved with mixture before extraction, until extractant therein volatilizees completely,
Obtain mixture.
It preferably, further include the operation of the lutein obtained to extraction and quercetagetin separation, concrete operations are to use
The mixture that n-hexane obtains extraction extracts.
Preferably, the mass volume ratio of the mixture and the n-hexane is less than 1:3.
It is further preferred that the mass volume ratio of the mixture and the n-hexane is 1:3~5.
Preferably, the temperature of extraction is 20~55 DEG C, extraction time 2-8h.
Preferably, described to extract the operation progress that this field routine can be used.
As a preferred option, the method for the present invention includes following steps:
1) mixed liquor of the n-hexane and the acetone soln is used to extract as extractant to marigold flower particle,
Extracting solution to extractant is volatilized completely, obtains mixture, the volume fraction of acetone is 80~100% in the acetone soln；Just
The volume ratio of hexane and the acetone soln is less than 1:3；The mass volume ratio of the marigold flower particle and the extractant is small
In 1:4；
2) mixture is extracted with n-hexane, is then separated by solid-liquid separation, solid phase is dried to obtain ten thousand longevity of quercitrin
Chrysanthemum element product obtains lutein product after liquid phase concentration.
Extracted by above-mentioned preferred scheme, the yield of quercitrin marigold 90% or more, purity 95% or more,
Also ensure lutein also yield with higher.
Still more preferably, in above scheme, the volume ratio of the n-hexane and the acetone soln is 1:3~5；Institute
The mass volume ratio for stating marigold flower particle and the extractant is 1:4~7.
, can be in the purity for realizing quercetagetin 95% or more by above-mentioned further preferred operations, yield exists
Production cost is preferably reduced under the premise of 90% or more, is more advantageous to industrialized large-scale application.
Acetone soln of the present invention is the aqueous solution of acetone, and quality and volume are mark in the mass volume ratio
Quasi- unit, than during gram corresponding milliliter, it is kilogram corresponding to rise.
The lutein product and quercetagetin that it is another object of the present invention to protect method of the invention to be prepared
Product.
The invention has the following beneficial effects:
1) method of the invention obtains the quercetagetin of high-purity by the way that simple extraction step is extractable, and gained produces
Product can be directly applied for industrialized production.After further preferred scheme, the purity of quercetagetin is 95% or more, Mongolian oak
The yield of skin patuletin is 90% or more, compared with passing through the complicated method such as chromatography in the prior art, be it is a kind of very
The method for efficiently extracting quercetagetin, extraction cost is low, time-consuming is short, is suitable for industrialized large-scale production.
2) method of the invention is also extractable while extracting quercetagetin obtains good lutein, purity
Greater than 18%, yield is greater than 99%, and the separation method of the two is very simple, only carries out simple extraction by n-hexane and is
Can, it is easy to operate.
3) water is not added during extraction in method of the invention, is not required to distillation solvent, and process costs are cheap, and no waste water produces
It is raw, it is environmentally protective.
Detailed description of the invention
Fig. 1 is the liquid chromatogram of 1 gained quercetagetin product of embodiment.
Specific embodiment
The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention..
Marigold flower particle involved in embodiment be by marigold flower through everfermentation, squeezing, drying, crushing, pelletize
The marigold flower particle arrived.
Embodiment 1
The present embodiment is related to extracting method of the present invention, includes the following steps:
(1) feed intake 100kg marigold flower particle, with n-hexane and 80% acetone soln with volume ratio 1:3 mixing, to described
Marigold flower particle extracts at 20 °C according to total solid-liquid ratio 1:4, and the time extracted every time is 1h, repeats after extracting 3 times
Leaching liquor is mixed, leaching liquor is concentrated into no distillate, obtains solid mixture 24.47kg；
(2) n-hexane is added with mass volume ratio 1:3 to mixture obtained in (1) to be extracted, extracts at room temperature
Then 3h carries out solid-liquid double-phase separation, respectively obtains the liquid phase containing lutein and the solid phase containing quercetagetin；
(3) the lutein liquid phase in (2) is concentrated up to lutein product 18.59kg, through liquid-phase chromatographic analysis, purity
It is 18.02%, content yield is 99.25%.
(4) by the quercetagetin solid phase drying to obtain quercetagetin product 5.88kg in (2), through liquid phase color
(liquid chromatogram such as Fig. 1, peak is quercetagetin to spectrum analysis between 4.0min~4.5min in figure, and appearance time is
4.131), purity 95.15%, content yield are 90.24%.
Embodiment 2
The present embodiment is related to extracting method of the present invention, includes the following steps:
(1) feed intake 100kg marigold flower particle, is mixed with the acetone of n-hexane and 100% with volume ratio 1:3, to described
Marigold flower particle is extracted according to the material ratio of 1:6 in 55 DEG C of conditions, and the time extracted every time is 1h, and repeating will after extracting 3 times
Leaching liquor mixing, is then concentrated into no distillate, obtains solids 23.81kg；
(2) n-hexane is added with mass volume ratio 1:5 to mixture obtained in (1) to be extracted, is extracted at 30 DEG C
Then 3h carries out solid-liquid double-phase separation, respectively obtains liquid phase lutein phase and solid phase quercetagetin phase.
(3) the lutein liquid phase in (2) is concentrated up to lutein product 17.81kg.Through liquid-phase chromatographic analysis, purity
It is 18.9%, content yield is 99.76%.
(4) by the quercetagetin solid phase drying to obtain quercetagetin product 5.99kg in (2), through liquid phase color
Spectrum analysis, purity 96.17%, content yield are 92.94%.
Embodiment 3
The present embodiment is related to extracting method of the present invention, includes the following steps:
(1) feed intake 100kg marigold flower particle, is mixed with the acetone soln of n-hexane and 100% with volume ratio 1:5, right
The marigold flower particle extracts under the conditions of 55 DEG C according to the material ratio of 1:6, and the time extracted every time is 1h, repeats to extract 3
Leaching liquor is mixed after secondary, leaching liquor is then concentrated into no distillate, obtains solid mixture 24.06kg；
(2) n-hexane is added with mass volume ratio 1:5 to mixture obtained in (1) to be extracted, is extracted at 50 DEG C
Then 3h carries out solid-liquid double-phase separation, respectively obtains liquid phase lutein liquid phase and solid phase quercetagetin phase.
(3) the lutein liquid phase in (2) is concentrated up to lutein product 18.04kg.Through liquid-phase chromatographic analysis, purity
It is 18.6%, content yield is 99.41%
(4) by the quercetagetin solid phase drying to obtain quercetagetin product 6.02kg in (2), through liquid phase color
Spectrum analysis, purity 96.48%, content yield are 93.73%.
Comparative example 1
Compared with Example 3, difference is, in the step 1), the volume ratio of n-hexane and acetone soln is 1:2.
Lutein liquid phase in step (2) is concentrated up to lutein product 17.54kg.It is pure through liquid-phase chromatographic analysis
Degree is 18.61%, and content yield is 96.71%.
By the quercetagetin solid phase drying to obtain quercetagetin product 5.07kg in (2), through liquid chromatogram
Analysis, purity 95.76%, content yield are 78.24%.
Comparative example 2
Compared with Example 3, difference is that in the step 1), the volume fraction of the middle acetone of acetone soln is
70%.
Lutein liquid phase in step (2) is concentrated up to lutein product 16.56kg.It is pure through liquid-phase chromatographic analysis
Degree is 18.79%, and content yield is 92.21%.
By the quercetagetin solid phase drying to obtain quercetagetin product 7.14kg in (2), through liquid chromatogram
Analysis, purity 79.16%, content yield are 91.22%.
Comparative example 3
Compared with Example 3, difference be, in the step 2), extracted with ethyl acetate solvent, mixture with
The mass volume ratio of extract liquor is 1:4.
Lutein liquid phase in step (2) is concentrated up to lutein product 16.45kg.It is pure through liquid-phase chromatographic analysis
Degree is 13.76%, and content yield is 67.08%.
By the quercetagetin solid phase drying to obtain quercetagetin product 7.35kg in (2), through liquid chromatogram
Analysis, purity 75.68%, content yield are 89.77%.
Comparative example 4
Compared with Example 3, difference is, in the step 1), marigold flower particle and Extraction solvent ratio are 1:2.
Lutein liquid phase in step (2) is concentrated up to lutein product 14.69kg.It is pure through liquid-phase chromatographic analysis
Degree is 18.62%, and content yield is 81.03%.
By the quercetagetin solid phase drying to obtain quercetagetin product 4.51kg in (2), through liquid chromatogram
Analysis, purity 95.23%, content yield are 69.27%.
Although above having used general explanation, specific embodiment and test, the present invention is made to retouch in detail
It states, but on the basis of the present invention, it can be made some modifications or improvements, this is apparent to those skilled in the art
's.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to claimed
Range.
Claims (10)
1. a kind of industrial method for quickly and efficiently extracting lutein and quercetagetin, which is characterized in that with n-hexane
Marigold flower particle is extracted as extractant with the mixed liquor of acetone soln, the volume of acetone point in the acetone soln
Number is 80~100%.
2. industrial method according to claim 1, which is characterized in that the volume of the n-hexane and the acetone soln
Than being less than 1:3.
3. industrial method according to claim 1 or 2, which is characterized in that the n-hexane and the acetone soln
Volume ratio is 1:3~5.
4. described in any item industrial methods according to claim 1~3, which is characterized in that the marigold flower particle and institute
The mass volume ratio for stating extractant is less than 1:4.
5. industrial method according to any one of claims 1 to 4, which is characterized in that the marigold flower particle and institute
The mass volume ratio for stating extractant is 1:4~7.
6. described in any item industrial methods according to claim 1~5, which is characterized in that further include extraction is obtained it is mixed
The operation that object is separated is closed, specifically, being extracted with the mixture that n-hexane obtains extraction.
7. industrial method according to claim 6, which is characterized in that the mass body of the mixture and the n-hexane
Product is than being less than 1:3；Preferably, the mass volume ratio of the mixture and the n-hexane is 1:3~5.
8. described in any item industrial methods according to claim 1~7, which is characterized in that Extracting temperature is 20~55 DEG C, is mentioned
Taking the time is 2~8h；And/or extraction temperature is 20-55 DEG C, extraction time 2-8h.
9. described in any item industrial methods according to claim 1~8, which comprises the steps of:
1) marigold flower particle is extracted using the mixed liquor of the n-hexane and the acetone soln as extractant, by institute
Extracting solution is concentrated into extractant and all volatilizes, obtain mixture；In the acetone soln volume fraction of acetone be 80~
100%；The volume ratio of the n-hexane and the acetone soln is less than 1:3；The marigold flower particle and the extractant
Mass volume ratio is less than 1:4；
2) mixture is extracted with n-hexane, is then separated by solid-liquid separation, solid phase is dried to obtain quercetagetin
Product obtains lutein product after liquid phase concentration.
10. lutein product and quercetagetin product that any one of claim 1~9 method is prepared.
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| CN201910397773.0A CN110003071B (en) | 2019-05-14 | 2019-05-14 | Industrial method for quickly and efficiently extracting lutein and quercetagetin |
| PCT/CN2020/090320 WO2020228786A1 (en) | 2019-05-14 | 2020-05-14 | Industrialized method for rapidly and efficiently extracting xanthophyll and quercetagetin |
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| CN110746331A (en) * | 2019-10-22 | 2020-02-04 | 晨光生物科技集团股份有限公司 | Industrial method for extracting lutein and quercetagetin from marigold |
| CN110776449A (en) * | 2019-10-22 | 2020-02-11 | 晨光生物科技集团股份有限公司 | Industrial method for extracting lutein and quercetagetin |
| WO2020228786A1 (en) * | 2019-05-14 | 2020-11-19 | 晨光生物科技集团股份有限公司 | Industrialized method for rapidly and efficiently extracting xanthophyll and quercetagetin |
| CN113367337A (en) * | 2020-03-10 | 2021-09-10 | 晨光生物科技集团股份有限公司 | A composition containing quercetagetin |
| CN114052247A (en) * | 2020-08-06 | 2022-02-18 | 晨光生物科技集团股份有限公司 | An antioxidant composition containing quercetagetin, 6-hydroxy kaempferol and gallic acid |
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| CN110776449A (en) * | 2019-10-22 | 2020-02-11 | 晨光生物科技集团股份有限公司 | Industrial method for extracting lutein and quercetagetin |
| CN110776449B (en) * | 2019-10-22 | 2021-04-09 | 晨光生物科技集团股份有限公司 | Industrial method for extracting lutein and quercetagetin |
| CN110746331B (en) * | 2019-10-22 | 2021-04-09 | 晨光生物科技集团股份有限公司 | Industrial method for extracting lutein and quercetagetin from marigold |
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| CN113367337A (en) * | 2020-03-10 | 2021-09-10 | 晨光生物科技集团股份有限公司 | A composition containing quercetagetin |
| WO2021180117A1 (en) * | 2020-03-10 | 2021-09-16 | 晨光生物科技集团股份有限公司 | Composition comprising quercetagetin |
| CN113367337B (en) * | 2020-03-10 | 2023-02-24 | 晨光生物科技集团股份有限公司 | A composition containing quercetagetin |
| CN114052247A (en) * | 2020-08-06 | 2022-02-18 | 晨光生物科技集团股份有限公司 | An antioxidant composition containing quercetagetin, 6-hydroxy kaempferol and gallic acid |
| CN114052247B (en) * | 2020-08-06 | 2023-06-16 | 晨光生物科技集团股份有限公司 | An antioxidant composition containing quercetin, 6-hydroxy kaempferol and gallic acid |
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| CN110003071B (en) | 2021-03-23 |
| WO2020228786A1 (en) | 2020-11-19 |
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