CN112500716B - Application of natural eutectic solvent in selective extraction and storage of anthocyanin - Google Patents
Application of natural eutectic solvent in selective extraction and storage of anthocyanin Download PDFInfo
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- CN112500716B CN112500716B CN202011503951.2A CN202011503951A CN112500716B CN 112500716 B CN112500716 B CN 112500716B CN 202011503951 A CN202011503951 A CN 202011503951A CN 112500716 B CN112500716 B CN 112500716B
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
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Abstract
The invention discloses an application of a natural eutectic solvent in selective extraction of anthocyanin, which comprises the following steps: uniformly mixing the water solution of the natural eutectic solvent and the blueberry pomace powder, and extracting the anthocyanin crude extract under the ultrasonic and water bath heating conditions; the natural eutectic solvent takes choline chloride as a hydrogen bond acceptor and oxalic acid as a hydrogen bond donor; the mol ratio of choline chloride to oxalic acid is 1: 0.5 to 2; in the water solution of the natural eutectic solvent, the mass ratio of water to the natural eutectic solvent is 10-50%; the anthocyanin crude extract can be used to obtain anthocyanin containing delphinidin-3-galactoside, delphinidin-3-arabinoside and malvidin-3-arabinoside as main ingredients. The invention also discloses application of the natural eutectic solvent in anthocyanin preservation. The eutectic solvent has strong selectivity on delphinidin-3-galactoside, delphinidin-3-arabinoside and malvidin-3-arabinoside, and can effectively improve the stability of the delphinidin-3-galactoside.
Description
Technical Field
The invention relates to the technical field of food science and engineering, in particular to application of a natural eutectic solvent in selective extraction and storage of anthocyanin.
Background
Anthocyanin belongs to flavonoid compounds and is widely present in fruits, vegetables and coarse cereals which are consumed by people in daily life. The anthocyanin can present various colors according to the variety and conditions of the specific anthocyanin, is safe and nontoxic, and has wide physiological activities of resisting oxidation, resisting inflammation, resisting cancer, reducing blood sugar and blood fat, protecting internal organs from oxidative stress damage, inhibiting obesity and the like. In recent years, the pigment is increasingly used in the field of food processing to replace the traditional artificial synthetic pigment. Anthocyanin with partial source is already listed in the national standard of Chinese food additives (GB2760-2014), and can be added into foods such as cakes, jelly, soft drinks, prepared wine, frozen drinks and the like according to the standard. In addition, the product has certain health care value, and is often added into functional food or health care products, so that the commercial added value of the product is improved while the color and luster of the product are improved.
Anthocyanins can be divided into six major classes depending on the degree of hydroxylation and methylation of the B ring of the anthocyanin. Delphinidin-3-galactoside, delphinidin-3-arabinoside and malvidin-3-arabinoside are common dietary anthocyanins, but the existing extraction process lacks selectivity on anthocyanin or mostly focuses on extraction and preparation of cyanidin-3-glucoside, and green and economic extraction schemes with strong selectivity on delphinidin-3-galactoside, delphinidin-3-arabinoside and malvidin-3-arabinoside are still rarely reported.
At present, the existing anthocyanin substance extraction technology on the market is more concentrated on the traditional organic solvent extraction method, which generally causes lower extraction efficiency, environmental pollution and potential harm to human health caused by the residue of the extraction solvent. The natural eutectic solvent is a novel green extraction solvent, is generally considered to be a good substitute for the conventional extraction solvent because it is non-volatile, non-flammable, stable at normal temperature, and based on natural components present in numerous cells and tissues. In addition, as the hydrogen bond donor and the hydrogen bond acceptor of the natural eutectic solvent are of various molecular species, the solvents with different polarity, solubility and other physical and chemical properties can be customized through different hydrogen bond donor-acceptor combination schemes; meanwhile, anthocyanin substances are poor in stability and are easily induced to generate chemical changes by various factors (such as temperature, pH, oxygen, illumination and the like) in the environment, so that the color development and the physiological activity of the anthocyanin substances are influenced. Ultrasonic-assisted extraction is a technology commonly used for extracting anthocyanin substances, but the problem of local high-temperature overheating near an ultrasonic probe is difficult to solve, so that a great amount of anthocyanin is lost in the extraction process. In addition, in the subsequent treatment process of the unitized operation, there are also scenes of high-temperature heating, pH change, illumination and other environments, so that the extraction technology has the effect of improving the stability of anthocyanin in a complex environment on the basis of having a certain selectivity, and has also received extensive attention in scientific research and industrial industries in the field.
At present, an extraction method which has stronger selectivity on delphinidin-3-galactoside, delphinidin-3-arabinoside and malvidin-3-arabinoside and can effectively protect the stability of the delphinidin-3-galactoside is urgently needed.
Disclosure of Invention
The invention provides an application of a natural eutectic solvent in selective extraction of anthocyanin, wherein the natural eutectic solvent has stronger selectivity on delphinidin-3-galactoside, delphinidin-3-arabinoside and malvidin-3-arabinoside, and can effectively improve the stability of the natural eutectic solvent.
The technical scheme of the invention is as follows:
the application of a natural eutectic solvent in selective extraction of anthocyanin comprises the following steps:
(1) freezing, freeze-drying, crushing and grinding the freshly squeezed blueberry pomace to obtain blueberry pomace powder;
(2) uniformly mixing an aqueous solution of a natural eutectic solvent and blueberry pomace powder, extracting anthocyanin in the blueberry pomace powder under the heating conditions of ultrasound and water bath, centrifuging, and collecting supernatant to obtain a crude anthocyanin extracting solution;
the natural eutectic solvent contains choline chloride and oxalic acid, the choline chloride is used as a hydrogen bond acceptor, and the oxalic acid is used as a hydrogen bond donor; the mol ratio of choline chloride to oxalic acid is 1: 0.5 to 2;
in the water solution of the natural eutectic solvent, the mass ratio of water to the natural eutectic solvent is 10-50%;
(3) the anthocyanin crude extract is subjected to solid phase extraction to obtain an anthocyanin purified solution, and the anthocyanin with delphinidin-3-galactoside, delphinidin-3-arabinoside and malvidin-3-arabinoside as main components can be obtained after concentration and drying.
The natural eutectic solvent has strong selectivity on delphinidin-3-galactoside, delphinidin-3-arabinoside and malvidin-3-arabinoside, and anthocyanin with delphinidin-3-galactoside, delphinidin-3-arabinoside and malvidin-3-arabinoside as main components can be selectively extracted from blueberry pomace.
Preferably, in the aqueous solution of the natural eutectic solvent, the mass ratio of water to the natural eutectic solvent is 30-35%.
Preferably, during the process of preparing the aqueous solution of the natural eutectic solvent, a water bath at 75-85 ℃ is adopted for heating, and stirring is continuously carried out, so as to avoid local denaturation of the natural eutectic solvent.
Preferably, in the step (1), the blueberry pomace is frozen in a dark condition, pre-frozen at-15 to-60 ℃ for 12 to 24 hours, and then vacuum freeze-dried for 24 to 36 hours.
Preferably, in the step (2), the liquid-solid ratio of the water solution of the natural eutectic solvent to the blueberry pomace powder is 50-70 mL/g.
Preferably, in the step (2), when the aqueous solution of the natural eutectic solvent is mixed with the blueberry pomace powder, the mixture is preheated for 3-10min in a water bath at 30-50 ℃ so that the blueberry pomace powder is uniformly diffused in the aqueous solution of the natural eutectic solvent.
Preferably, in the step (2), the ultrasonic power is 240-; the heating temperature of the water bath is 65-85 ℃.
The invention also provides application of the natural eutectic solvent in anthocyanin preservation, which comprises the step of dissolving anthocyanin in an aqueous solution of the natural eutectic solvent.
The natural eutectic solvent can obviously improve the stability of anthocyanin under the conditions of high temperature, different pH environments and different illumination conditions and inhibit the degradation of anthocyanin.
The natural eutectic solvent has stronger selectivity on delphinidin-3-galactoside, delphinidin-3-arabinoside and malvidin-3-arabinoside, can effectively improve the stability of the natural eutectic solvent, can overcome the defects of low efficiency, environmental pollution, potential harm of residues to human health and the like of the traditional extraction solvent, has pertinence on the extraction of a target object, effectively protects the stability of the target object in the extraction process and the subsequent processing and storage processes, and has important significance on the quality and efficiency improvement of industry, the construction of a green economy and sustainable development type society.
Compared with the traditional acidified aqueous solution or acidified ethanol solution as an extraction solvent, the method has the beneficial effects that:
(1) the natural eutectic solvent can obviously improve the selectivity and extraction efficiency of delphinidin-3-galactoside, delphinidin-3-arabinoside and malvidin-3-arabinoside in blueberry pomace;
(2) the natural eutectic solvent provided by the invention obviously improves the stability of the extracted anthocyanin under the conditions of high temperature, different pH environments and different illumination conditions, inhibits the degradation of the anthocyanin, and can be used as a storage and protection scheme for extracting the anthocyanin on the basis of being used as an extraction scheme;
(3) the solvent used in the extraction method is the natural eutectic solvent which is subjected to optimized screening, so that the extraction efficiency is improved, the green and safe extraction is ensured, the environment is not polluted, the cost is low, and the method is suitable for large-scale amplification;
(4) compared with other methods, the method provided by the invention is simple to operate, easy to train and use, short in process time consumption and low in energy consumption.
Drawings
FIG. 1 is a comparison graph of the ratio of delphinidin-3-galactoside/arabinoside and malvidin-3-arabinoside to total anthocyanin extracted from blueberry anthocyanin by different extraction methods;
FIG. 2 is a comparison graph of the total amount of delphinidin-3-galactoside/arabinoside and malvidin-3-arabinoside extracted from blueberry anthocyanin by different extraction methods;
FIG. 3 is a graph showing the degradation of anthocyanin in a solvent at various temperatures for different extraction methods;
FIG. 4 is a graph of the degradation of anthocyanin in a solvent at various extraction methods in a single pH environment;
FIG. 5 is a graph of the degradation of anthocyanin in solvents of different extraction methods under different light environments.
Detailed Description
Example 1
The embodiment provides a method for extracting delphinidin-3-galactoside/arabinoside and malvidin-3-arabinoside from blueberry pomace with high selectivity and simultaneously protecting the stability of the delphinidin-3-arabinoside, which comprises the following steps of:
step (1): freezing the fresh blueberry pomace at-20 ℃ for 24 hours, then carrying out vacuum freeze drying in a large freeze dryer for 36 hours, crushing and grinding, and keeping the whole process away from light;
step (2): choline chloride is used as a hydrogen bond receptor, oxalic acid is used as a hydrogen bond donor, the two are in a molar ratio of 2:1, water bath heating is adopted for 80 ℃ and stirring is not stopped, local denaturation is avoided, clear, transparent and uniform liquid (natural eutectic solvent) is obtained, water is added in an amount of 30% (w/w, mass ratio of water to the natural eutectic solvent), the clear, transparent and uniform liquid and the natural eutectic solvent are mixed with the sample powder in the step (1), the liquid-solid ratio is 50mL/g, and the sample powder is preheated in water bath at 45 ℃ for 5min, so that the sample powder is uniformly diffused in the natural eutectic solvent;
and (3): extracting with the assistance of a pulse type ultrasonic crusher, wherein the ultrasonic power is 300W, the ultrasonic extraction time is 3min, the temperature of a circulating water bath is controlled at 73 ℃, centrifuging and collecting supernatant to obtain a crude extract taking target anthocyanin delphinidin-3-galactoside/arabinoside and malvidin-3-arabinoside as main anthocyanins, and simultaneously, the crude extract can also be directly used as an in-situ storage means of the anthocyanins;
and (4): adsorbing with C18 solid phase extraction column, desorbing, purifying the crude extractive solution to obtain anthocyanin purified solution containing delphinidin-3-galactoside/arabinoside and malvidin-3-arabinoside as main ingredients, concentrating, and drying to obtain the final product.
Example 2
The embodiment provides a technical scheme for extracting delphinidin-3-galactoside/arabinoside and malvidin-3-arabinoside from blueberry pomace with high selectivity and simultaneously protecting the stability of the delphinidin-3-arabinoside, which comprises the following steps:
step (1): freezing the fresh fruit residues at-40 deg.C for 24 hr, vacuum freeze-drying in large freeze-dryer for 36 hr, crushing, grinding, and keeping away from light;
step (2): choline chloride is used as a hydrogen bond receptor, oxalic acid is used as a hydrogen bond donor, the molar ratio is 1:1, the mixture is heated by water bath at 80 ℃ and stirred continuously to avoid local denaturation, clear, transparent and uniform liquid is obtained, the water is added in an amount of 30% (w/w), the mixture is mixed with the sample powder in the step (1), the liquid-solid ratio is 60mL/g, and the mixture is preheated at 45 ℃ for 5min to ensure that the sample powder is uniformly diffused in a natural eutectic solvent;
and (3): extracting with the assistance of a pulse type ultrasonic crusher, wherein the ultrasonic power is 325W, the ultrasonic extraction time is 3min, the temperature of a circulating water bath is controlled at 76 ℃, and centrifuging and collecting supernatant to obtain a crude extract taking target anthocyanin delphinidin-3-galactoside/arabinoside and malvidin-3-arabinoside as main anthocyanins, and simultaneously, the crude extract can also be directly used as an in-situ storage means of the anthocyanins;
and (4): adsorbing with C18 solid phase extraction column, desorbing, purifying the crude extractive solution to obtain anthocyanin purified solution containing delphinidin-3-galactoside/arabinoside and malvidin-3-arabinoside as main ingredients, concentrating, and drying to obtain the final product.
Example 3
The embodiment provides a technical scheme for extracting delphinidin-3-galactoside/arabinoside and malvidin-3-arabinoside from blueberry pomace with high selectivity and simultaneously protecting the stability of the delphinidin-3-arabinoside, which comprises the following steps:
step (1): freezing the fresh fruit residues at-60 deg.C for 24 hr, vacuum freeze-drying in large freeze-dryer for 24 hr, crushing, grinding, and keeping away from light;
step (2): choline chloride is used as a hydrogen bond receptor, oxalic acid is used as a hydrogen bond donor, the molar ratio is 1:2, the mixture is heated by water bath at 80 ℃ and stirred continuously to avoid local denaturation, clear, transparent and uniform liquid is obtained, the water is added in an amount of 30% (w/w), the mixture is mixed with the sample powder in the step (1), the liquid-solid ratio is 60mL/g, and the mixture is preheated at 40 ℃ for 8min to ensure that the sample powder is uniformly diffused in a natural eutectic solvent;
and (3): extracting with the aid of a pulse type ultrasonic crusher, controlling the ultrasonic power at 340W, the ultrasonic extraction time at 4min, controlling the temperature of a circulating water bath at 78 ℃, centrifuging, and collecting supernatant to obtain a crude extract taking target anthocyanin delphinidin-3-galactoside/arabinoside and malvidin-3-arabinoside as main anthocyanins, and simultaneously, the crude extract can also be directly used as an in-situ storage means of the anthocyanins;
and (4): adsorbing with C18 solid phase extraction column, desorbing, purifying the crude extractive solution to obtain anthocyanin purified solution containing delphinidin-3-galactoside/arabinoside and malvidin-3-arabinoside as main ingredients, concentrating, and drying to obtain the final product.
Example 4
The embodiment provides a technical scheme for extracting delphinidin-3-galactoside/arabinoside and malvidin-3-arabinoside from blueberry pomace with high selectivity and simultaneously protecting the stability of the delphinidin-3-arabinoside, which comprises the following steps:
step (1): freezing the fresh fruit residues at-60 deg.C for 24 hr, vacuum freeze-drying in large freeze-dryer for 24 hr, crushing, grinding, and keeping away from light;
step (2): choline chloride is used as a hydrogen bond receptor, oxalic acid is used as a hydrogen bond donor, the molar ratio is 1:1, the mixture is heated by water bath at 80 ℃ and stirred continuously to avoid local denaturation, clear, transparent and uniform liquid is obtained, 35% (w/w) of water is added to be mixed with the sample powder in the step (1), the liquid-solid ratio is 65mL/g, and the mixture is preheated at 45 ℃ for 6min to ensure that the sample powder is uniformly diffused in a natural eutectic solvent;
and (3): extracting with the assistance of a pulse type ultrasonic crusher, wherein the ultrasonic power is 350W, the ultrasonic extraction time is 4min, the temperature of a circulating water bath is controlled at 80 ℃, centrifuging and collecting supernatant to obtain a crude extract taking target anthocyanin delphinidin-3-galactoside/arabinoside and malvidin-3-arabinoside as main anthocyanins, and simultaneously, the crude extract can also be directly used as an in-situ storage means of the anthocyanins;
and (4): adsorbing with C18 solid phase extraction column, desorbing, purifying the crude extractive solution to obtain anthocyanin purified solution containing delphinidin-3-galactoside/arabinoside and malvidin-3-arabinoside as main ingredients, concentrating, and drying to obtain the final product.
To verify the technical effects of the present invention, the following experiments are described as examples:
1. the extraction effects of delphinidin-3-galactoside/arabinoside and malvidin-3-arabinoside (three anthocyanins for short, the same below) were compared under different extraction conditions.
The same blueberry pomace sample is extracted by a conventional extraction method (solvent is 0.1% acidified ethanol (abbreviated as ethanol), extraction temperature is 70 ℃, ultrasonic power is 325W, extraction time is 4min, liquid-solid ratio is 60mL/g) and the extraction method of the invention (solvent is 30% water content (W/W) and choline chloride-oxalic acid natural eutectic solvent (short for Choa) with molar ratio of 1:1, extraction temperature is 70 ℃, ultrasonic power is 325W, extraction time is 4min, and liquid-solid ratio is 60mL/g), and the result is shown in figure 1 and figure 2.
As can be seen from fig. 1 and fig. 2, the extraction method of the invention can greatly improve the specific gravity of the three target anthocyanins in the total anthocyanins, and the content of the three target anthocyanins is more than three times of that of the conventional ultrasonic-assisted extraction method.
2. And (3) comparing the degradation of anthocyanin in the solvents of different extraction methods under different temperature, pH and illumination environments.
Respectively extracting the same blueberry pomace sample by a conventional extraction method (the solvent is 0.1% acidified ethanol (abbreviated as ethanol), the extraction temperature is 76 ℃, the ultrasonic power is 325W, the extraction time is 3min, and the liquid-solid ratio is 60mL/g) and the extraction method (the solvent is 30% choline chloride-oxalic acid natural eutectic solvent (abbreviated as Choa) with the water content (W/W) and the molar ratio of 1: 1), the extraction temperature is 76 ℃, the ultrasonic power is 325W, the extraction time is 3min, and the liquid-solid ratio is 60mL/g) to obtain extracting solutions, and then respectively carrying out stability tests under different temperatures (-4-80 ℃), different pH values (pH 1-6), different illumination conditions (light shielding, indoor fluorescent lamp tube natural illumination, summer sunlight), and the results are shown in fig. 3, fig. 4 and fig. 5.
As can be seen from the fig. 3, 4 and 5, the solvent adopted in the extraction method of the invention can effectively protect the stability of anthocyanin in high temperature, different pH environments and illumination environments, and the degradation rate under the same condition is greatly reduced compared with that of the traditional acidified ethanol solution. Therefore, the solvent adopted in the extraction method can effectively reduce the loss of anthocyanin caused by local high temperature of the ultrasonic probe in the extraction process, and meanwhile, the solvent has great advantages as a preservation solution of the extracted anthocyanin.
The above-mentioned embodiments are intended to illustrate the technical solutions and advantages of the present invention, and it should be understood that the above-mentioned embodiments are only specific embodiments of the present invention, and are not intended to limit the present invention, and any modifications, additions, equivalents, etc. made within the scope of the principles of the present invention should be included in the scope of the present invention.
Claims (8)
1. The application of the natural eutectic solvent in selective extraction of anthocyanin is characterized by comprising the following steps:
(1) freezing, freeze-drying, crushing and grinding the freshly squeezed blueberry pomace to obtain blueberry pomace powder;
(2) uniformly mixing an aqueous solution of a natural eutectic solvent and blueberry pomace powder, extracting anthocyanin in the blueberry pomace powder under the heating conditions of ultrasound and water bath, centrifuging, and collecting supernatant to obtain a crude anthocyanin extracting solution;
the natural eutectic solvent contains choline chloride and oxalic acid, the choline chloride is used as a hydrogen bond acceptor, and the oxalic acid is used as a hydrogen bond donor; the mol ratio of choline chloride to oxalic acid is 1: 0.5 to 2;
in the water solution of the natural eutectic solvent, the mass ratio of water to the natural eutectic solvent is 10-50%;
(3) the anthocyanin crude extract is subjected to solid phase extraction to obtain an anthocyanin purified solution, and the anthocyanin with delphinidin-3-galactoside, delphinidin-3-arabinoside and malvidin-3-arabinoside as main components can be obtained after concentration and drying.
2. The use of the natural eutectic solvent in the selective extraction of anthocyanin according to claim 1, wherein the mass ratio of water to the natural eutectic solvent in the aqueous solution of the natural eutectic solvent is 30-35%.
3. The use of the natural eutectic solvent in the selective extraction of anthocyanin according to claim 1, wherein in the preparation of the aqueous solution of the natural eutectic solvent, the natural eutectic solvent is heated in a water bath at 75-85 ℃ and is continuously stirred.
4. The application of the natural eutectic solvent in selective extraction of anthocyanin according to claim 1, wherein in the step (1), blueberry pomace is frozen under a dark condition, pre-frozen at-15 to-60 ℃ for 12 to 24 hours, and then vacuum freeze-dried for 24 to 36 hours.
5. The application of the natural eutectic solvent in selective extraction of anthocyanin according to claim 1, wherein in the step (2), the liquid-solid ratio of the water solution of the natural eutectic solvent to the blueberry pomace powder is 50-70 mL/g.
6. The use of the natural eutectic solvent in the selective extraction of anthocyanin according to claim 1, wherein in the step (2), the water solution of the natural eutectic solvent is preheated for 3-10min in a water bath at 30-50 ℃ when being mixed with the blueberry pomace powder.
7. The application of the natural eutectic solvent in selective extraction of anthocyanin according to claim 1, wherein in the step (2), the ultrasonic power is 240-360W, and the ultrasonic extraction time is 1-9 min; the heating temperature of the water bath is 65-85 ℃.
8. The application of a natural eutectic solvent in anthocyanin preservation is characterized in that anthocyanin is dissolved in an aqueous solution of the natural eutectic solvent;
the natural eutectic solvent contains choline chloride and oxalic acid, the choline chloride is used as a hydrogen bond acceptor, and the oxalic acid is used as a hydrogen bond donor; the mol ratio of choline chloride to oxalic acid is 1: 0.5 to 2;
in the water solution of the natural eutectic solvent, the mass ratio of water to the natural eutectic solvent is 10-50%;
the anthocyanin mainly comprises delphinidin-3-galactoside, delphinidin-3-arabinoside and malvidin-3-arabinoside.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6780442B2 (en) * | 2000-08-31 | 2004-08-24 | Hauser, Inc. | Efficient method for producing compositions enriched in anthocyanins |
| CN105622564A (en) * | 2016-03-21 | 2016-06-01 | 吉林大学 | Preparation method of blueberry anthocyanin aglycone |
| CN107936072A (en) * | 2017-12-12 | 2018-04-20 | 江苏省农业科学院 | A kind of method using eutectic solvent extraction blackberry anthocyanin |
| CN108078872A (en) * | 2018-02-07 | 2018-05-29 | 广东省农业科学院蚕业与农产品加工研究所 | Natural application of the eutectic solvent as preservative |
| WO2019219774A2 (en) * | 2018-05-16 | 2019-11-21 | Naturex S.A. | Eutectic extract formation and purification |
| CN110643196A (en) * | 2019-09-11 | 2020-01-03 | 暨南大学 | Extraction and separation method of anthocyanin |
-
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Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6780442B2 (en) * | 2000-08-31 | 2004-08-24 | Hauser, Inc. | Efficient method for producing compositions enriched in anthocyanins |
| CN105622564A (en) * | 2016-03-21 | 2016-06-01 | 吉林大学 | Preparation method of blueberry anthocyanin aglycone |
| CN107936072A (en) * | 2017-12-12 | 2018-04-20 | 江苏省农业科学院 | A kind of method using eutectic solvent extraction blackberry anthocyanin |
| CN108078872A (en) * | 2018-02-07 | 2018-05-29 | 广东省农业科学院蚕业与农产品加工研究所 | Natural application of the eutectic solvent as preservative |
| WO2019219774A2 (en) * | 2018-05-16 | 2019-11-21 | Naturex S.A. | Eutectic extract formation and purification |
| CN110643196A (en) * | 2019-09-11 | 2020-01-03 | 暨南大学 | Extraction and separation method of anthocyanin |
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