CN111892491A - High-efficiency curcumin extraction method - Google Patents

High-efficiency curcumin extraction method Download PDF

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Publication number
CN111892491A
CN111892491A CN202010803266.5A CN202010803266A CN111892491A CN 111892491 A CN111892491 A CN 111892491A CN 202010803266 A CN202010803266 A CN 202010803266A CN 111892491 A CN111892491 A CN 111892491A
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curcumin
solvent
extracting
extractant
filtering
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郑秋芳
方丽金
颜才健
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Fuzhou Forint Biotechnology Co ltd
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Fuzhou Forint Biotechnology Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives

Abstract

A high-efficiency curcumin extraction method comprises the following steps: the method comprises the following steps: adding an extracting agent A into the crushed turmeric powder, and filtering to obtain a solid material I; step two: adding an extracting agent B into the obtained solid material I, and filtering to remove residues to obtain an extracting solution II; step three: centrifuging the extracting solution II, and filtering to obtain a solid material III; step four: cleaning and drying the solid material III to obtain curcumin; the extractant A comprises a solvent a, and the solvent a has the following structure:
Figure 100004_DEST_PATH_IMAGE001
(1) in the formula (1), the reaction mixture is,
Figure 100004_DEST_PATH_IMAGE003
is composed of
Figure 100004_DEST_PATH_IMAGE004
、
Figure 100004_DEST_PATH_IMAGE006
、
Figure 100004_DEST_PATH_IMAGE007
、
Figure 100004_DEST_PATH_IMAGE009
、
Figure 100004_DEST_PATH_IMAGE011
One of (1); the extractant B comprises a solvent B, and the solvent B comprises the following components:
Figure 100004_DEST_PATH_IMAGE012
(2) in the formula (2), the reaction mixture is,

Description

High-efficiency curcumin extraction method
Technical Field
The invention belongs to the technical field of plant extraction and separation, and particularly relates to a high-efficiency extraction method of curcumin.
Background
Turmeric (Curcuma longa L.) is a perennial herb of Zingiberaceae, also known as Curcuma longa L, and is a traditional medicinal material with homology of medicine and food. The medicinal material value of turmeric means that dried rhizome thereof is widely cultivated in tropical and subtropical regions, particularly in southeast Asia and northern Australia, and is mainly distributed in China, Africa, USA, Japan, etc. The areas for planting the turmeric in China are more, and the method mainly focuses on Sichuan, Fujian, Hunan, Guangdong, Yunnan, Tibet, Guizhou, Taiwan and the like.
The turmeric has pungent, bitter and mild taste, enters heart, liver and spleen, has the effects of breaking blood and promoting qi circulation and stimulating the menstrual flow to stop bleeding, has a long medicinal history, is commonly used for treating chest pain, amenorrhea, abdominal mass, rheumatic pain, traumatic injury and other symptoms in ancient Chinese pharmacology, has the effects of antisepsis and sterilization, and can also be used for treating incised wound, burn and bruise. In addition, turmeric has a good health-care effect, and is also used for assisting in treating diseases such as stomachache, dyspepsia and the like. In the field of modern Chinese medicine, the preparation method is mainly used for producing Chinese medicine preparations.
The Curcuma rhizome mainly contains curcumin and Curcuma rhizome volatile oil, and also contains resins, saccharides, sterols, polypeptides, fatty acids, monoenoic acid, dienoic acid, alkaloids, trace elements, etc. In recent years, research on turmeric at home and abroad mainly focuses on the extraction and purification of active ingredients curcumin and curcuma oil and research on corresponding effects, and the aspects of separating and exploring new drugs from turmeric active ingredients, identifying structures, chemically synthesizing, modifying and the like are the key points of research of broad scholars.
Curcumin is a natural pigment, and is widely applied to foods such as cakes, candies, beverages, sausage products, cans and the like due to high colorability. Most of the existing artificial pigments can cause certain harm to human bodies, while curcumin serving as a natural pigment is almost non-toxic and harmless, and gradually replaces the artificial pigments. Curcumin is a slightly acidic diphenyl heptahydrocarbon substance, is an extremely rare diketone colored substance, and is a compound with a special structure of polyphenols. Commonly referred to curcumin generally refers to the collective name of curcumin (C21H 20O 6) monomer, demethoxycurcumin (C20H 18O 5) monomer and bisdemethoxycurcumin (C19H 16O 4) monomer. Curcumin is an orange crystalline powder, slightly bitter in taste, insoluble in water, soluble in ethanol, propylene glycol, glacial acetic acid and alkali solution. Therefore, by utilizing the characteristics of curcumin, the existing extraction method for turquoise generally comprises the following steps: ethanol reflux method, percolation method, sodium salicylate method, enzyme method, ultrasonic wave method, microwave extraction method, supercritical CO2 method, etc. Further purification is required to obtain a purer curcumin product, and methods for purifying curcumin generally include: organic solvent extraction, column chromatography, etc.
The ionic liquid is a salt which is in a liquid state at or near room temperature and completely consists of anions and cations, and is also called low-temperature molten salt. Compared with the traditional organic solvent, the ionic liquid has the advantages of low vapor pressure, wide viscosity range, good conductivity, strong dissolving capacity, high thermal stability and the like. Meanwhile, the ionic liquid has good designability, namely the polarity, the solubility, the hydrophobicity, the hydrophilicity and other physical and chemical properties of the ionic liquid can be adjusted through anion and cation combination or group modification. Since the ionic liquid has the above-mentioned advantages, it has attracted the attention of many researchers. For example, the document with the application number of 201711237710.6 discloses a method for extracting and preparing bamboo leaf flavone by using ionic liquid, which comprises the following process steps: adding crushed and sieved bamboo leaf powder into an ionic liquid aqueous solution A, performing ultrasonic-assisted extraction to obtain an extracting solution, and filtering the extracting solution to obtain a filtrate A and a solid material A; adding the solid material A into an ionic liquid aqueous solution B, performing ultrasonic-assisted extraction to obtain an extracting solution, and filtering the extracting solution to obtain a filtrate B; and adding an organic solvent into the filtrate B for extraction, standing for layering to obtain an upper organic phase extract and a lower raffinate, and concentrating the upper organic phase extract under reduced pressure to obtain the bamboo leaf total flavonoids. The method is a new process for extracting and preparing bamboo leaf flavone, the obtained bamboo leaf flavone has high extraction rate, high purity and quality, the ionic liquid can be recycled, the operation is convenient, and the method has good popularization and application prospects.
However, the ionic liquid is not suitable for curcumin extraction, the inventor researches and obtains an extraction method suitable for curcumin according to the property of the curcumin, researches the optimal process parameters of the curcumin extraction method by taking the curcumin yield as an investigation index, and determines the optimal purification process conditions.
Disclosure of Invention
Aiming at the problems, the invention aims to provide a high-efficiency extraction method of curcumin, which designs a set of specific extraction and purification method aiming at the characteristics of curcumin, has higher yield of the curcumin, greatly reduces the use of organic reagents and meets the requirement of environmental protection.
In order to achieve the purpose, the technical scheme of the invention is as follows:
a high-efficiency curcumin extraction method comprises the following steps: the method comprises the following steps: adding an extracting agent A into the crushed turmeric powder, and filtering to obtain a solid material I; step two: adding an extracting agent B into the obtained solid material I, and filtering to remove residues to obtain an extracting solution II; step three: centrifuging the extracting solution II, and filtering to obtain a solid material III; step four: cleaning and drying the solid material III to obtain curcumin; the extractant A comprises a solvent a, and the solvent a has the following structure:
Figure 100002_DEST_PATH_IMAGE001
（1）
in the formula (1), the reaction mixture is,
Figure 100002_DEST_PATH_IMAGE003
is composed of
Figure 100002_DEST_PATH_IMAGE004
、
Figure 100002_DEST_PATH_IMAGE006
、
Figure 100002_DEST_PATH_IMAGE007
、
Figure 100002_DEST_PATH_IMAGE009
、
Figure 100002_DEST_PATH_IMAGE011
One of (1);
the extractant B comprises a solvent B, and the solvent B comprises the following components:
Figure 100002_DEST_PATH_IMAGE012
（2）
in the formula (2), the reaction mixture is,
Figure 100002_DEST_PATH_IMAGE014
is metal chelating anion.
In the design of the scheme, a large number of hydrogen bonds exist in cell walls composed of cellulose and hemicellulose, the hydrogen bonds enable molecular chains to be mutually associated to form a highly crystallized crystalline region with a large density and an amorphous region with a small density, and a compact crystalline structure formed by a huge hydrogen bond network leads to good chemical and mechanical stability and hinders the dissolution of active ingredients such as curcumin and the like. Extraction adopted in the inventionThe solvent a contained in the agent A is imidazole ionic liquid: (1) firstly, the substituent on N at 3-position of imidazole ring adopts propenyl which has the advantage that propenyl is an unsaturated carbon chain consisting of three carbon atoms and one double bond, compared with commonly used C4The chain volume is smaller, so the ion mobility is better, the combination with cellulose is facilitated, the electron deficiency degree of cations is increased due to the existence of unsaturated bonds, the attack of the cations on hydroxyl atoms on cellulose and hemicellulose in the dissolving process is facilitated, and meanwhile, the liquid concentration of the ions is reduced due to the unsaturated chain structure, so that the extraction efficiency of the ionic liquid is increased. (2) Anion is taken
Figure 476147DEST_PATH_IMAGE004
、
Figure 862129DEST_PATH_IMAGE006
、
Figure 845128DEST_PATH_IMAGE007
、
Figure 961376DEST_PATH_IMAGE009
、
Figure 100002_DEST_PATH_IMAGE015
The anion groups have strong hydrogen bond accepting capacity and can form hydrogen bonds with hydrogen protons of hydroxyl groups on cellulose molecules, so that the hydrogen bonds between cellulose and hemicellulose are broken, and dissolution is further caused.
The solvent B contained in the extractant B is sulfonic acid modified metal chelating ionic liquid, and is functionalized ionic liquid based on imidazole ionic liquid, and the introduction of sulfonic acid groups can improve the selectivity and extraction capacity of aromatic hydrocarbon substances, so that the extraction rate of curcumin can be greatly improved; simultaneously, anions containing metal ions are introduced, and the advantages are that: (1) the metal-chelating anion has high structural stability and therefore does not change when reacting with a cation; (2) the ionic liquid has a structure similar to that of a surfactant, namely, the ionic liquid has a polar head and a non-polar tail at the same time, has a solubilization effect on curcumin, and is beneficial to improving the extraction rate of the curcumin; (3) meanwhile, the chelating metal anions can reduce the lattice energy of the ionic liquid, so that the ionic liquid is in a stable liquid state at room temperature; (4) meanwhile, the solvent B can be mixed with ethanol to obtain the extractant B, so that the extraction and purification of curcumin are realized in one step, and the subsequent separation process of ethanol can realize separation only by heating, distilling and recovering ethanol, so that the curcumin can be recycled.
According to a further preferable aspect of the invention, the extractant A is composed of the solvent a and deionized water, wherein the molar ratio of the solvent a to the deionized water is 1-4: 1.
As a further optimization of the invention, in the step one, the solid-to-liquid ratio of the turmeric powder to the extractant A is 1: 10-20 g/mL.
In a further preferred embodiment of the present invention, the extractant B is composed of the solvent B and absolute ethyl alcohol, wherein the volume ratio of the solvent B to the absolute ethyl alcohol is 1-4: 1.
As a further optimization of the invention, the solid-liquid ratio of the solid material I to the extracting agent B is 1: 10-15 g/mL.
In the design of the scheme, the extraction parameters are process optimization parameters obtained by the inventor through experimental design.
As a further preferred aspect of the present invention, the above-mentioned
Figure DEST_PATH_IMAGE016
Is composed of
Figure DEST_PATH_IMAGE018
Chelate compounds, preparation of
Figure 182273DEST_PATH_IMAGE018
The chelating agent used in the chelate is one of IDA, DTPA, EDTA, NTA, HFAC and IDS.
In the design of the scheme, the method comprises the following steps of,choose to use
Figure 722845DEST_PATH_IMAGE018
The obtained ionic liquid has stable property, can make the ionic liquid show a certain blue color, and is helpful for distinguishing, and iron ions with similar property are not selected because the iron ions can cause the activity of the curcumin to be damaged.
As a further preferred aspect of the present invention, the chelating agent is one of IDA and HFAC, and the chelating performance of the two chelating agents on copper ions is better than that of the other chelating agents.
As a further preferred embodiment of the present invention, the preparation process of the solvent b comprises: dissolving a chelating agent into acetonitrile, adding ammonia water, sealing, stirring at room temperature, and performing primary rotary evaporation to obtain a solid; and dissolving the obtained solid in ethanol, adding copper chloride, stirring at sealed room temperature, filtering, and performing secondary rotary evaporation to obtain a first metal chelate product.
As a further preferred embodiment of the present invention, the preparation process of the solvent b further comprises: mixing R-imidazole and 1, 3-propane sultone, adding acetone, stirring at 30-50 ℃, reacting to obtain a solid, acidifying the solid with concentrated acid, and washing and drying to obtain a second sulfonated ionic liquid product. The R-imidazole may be-CH3、-CH2=CH、-C2H5Etc., preferably-CH with a short chain length3。
As a further preferred embodiment of the present invention, the preparation process of the solvent b further comprises: and mixing the first metal chelate product and the second sulfonated ionic liquid product, reacting at sealed room temperature, filtering, performing third rotary evaporation, adding diethyl ether for dissolving, purifying, washing, performing fourth rotary evaporation, and drying to obtain a solvent b.
The invention has the following beneficial effects:
the extracting agent A adopted by the invention has excellent dissolving capacity on the cellulose and hemicellulose contained in the turmeric, so that the dissolution amount and dissolution rate of the curcumin can be improved, and the curcumin is selectively extracted by combining the extracting agent B, the extraction effect on the curcumin is further improved, and the extracting agent A and the extracting agent B have the characteristics of stability and easiness in separation and recovery, so that the use of organic solvents is reduced, and the requirements of environmental protection are met.
Detailed Description
Material preparation
Reagent: hexafluoroacetylacetone (HFAC, more than or equal to 99 percent), copper chloride dihydrate (more than or equal to 99 percent), ammonia water (25-28 percent), acetonitrile (more than or equal to 99 percent), ethanol (more than or equal to 99 percent), chloropropene (analytically pure), 1-vinyl imidazole (analytically pure), N-methyl imidazole (99 percent), formic acid (analytically pure), 1, 3-propane sultone (analytically pure), acetone (analytically pure), ethyl acetate (analytically pure), concentrated sulfuric acid (more than or equal to 99 percent), deionized water and the like.
Second, Experimental methods
1. Preparation of solvent a
N-methylimidazole (82.1 g/mol) and chloropropene (76.5 g/mol) in a mass ratio of 1:1 are weighed and added into a 250ml round-bottom flask, the mixture is refluxed for 24 hours under a water bath at 75 ℃ by electromagnetic stirring to stop the reaction, the mixture is transferred into a separating funnel and is kept stand for a while, the solution is divided into an upper layer and a lower layer, the lower layer is collected, then the substance is washed for 3 times by ethyl acetate, and impurities such as N-methylimidazole, chloropropene, ethyl acetate and the like are removed by a rotary evaporator under the condition of vacuumizing at 90 ℃. The reaction process is as follows:
Figure DEST_PATH_IMAGE020
the anion in the solvent a is selected from
Figure 927561DEST_PATH_IMAGE006
Are synthesized by a similar method, but taking into account
Figure 595303DEST_PATH_IMAGE006
And
Figure 998603DEST_PATH_IMAGE004
belonging to halogen atoms, of similar nature but
Figure 710075DEST_PATH_IMAGE006
It has color, and can influence curcumin extraction discrimination, so it is preferable
Figure 198826DEST_PATH_IMAGE004
。
The anion in the solvent a is selected from
Figure 404679DEST_PATH_IMAGE007
、
Figure 396906DEST_PATH_IMAGE009
、
Figure 561171DEST_PATH_IMAGE015
The preparation method is similar to that
Figure 786485DEST_PATH_IMAGE009
For example, [ Amim]Adding the Cl aqueous solution into an ion exchange column filled with strongly basic anion exchange resin at a proper flow rate to obtain [ Amim]An aqueous OH solution, then equimolar [ Amim]OH and formic acid are mixed for neutralization reaction, water is removed through reduced pressure distillation after full reaction, vacuum drying is carried out for 48 hours at 70 ℃, and the ionic liquid is obtained.
2. Preparation of solvent b
(1) Adding 10mmol hexafluoroacetylacetone (liquid) into a 250ml single-neck round-bottom flask, adding 50ml acetonitrile as a solvent, finally adding equimolar ammonia water, sealing, and reacting for 24 hours under magnetic stirring at room temperature. After the reaction is finished, 3.33mmol of copper chloride dihydrate is added, 20-30ml of ethanol is added for dissolution, and the mixture is stirred and reacted for 10-12h at room temperature. After the reaction is finished, a by-product ammonium chloride is filtered, and acetonitrile and ethanol are distilled off by a rotary evaporator to obtain a first metal chelate product. The reaction process is as follows:
Figure DEST_PATH_IMAGE021
the preparation process is similar to hexafluoroacetylacetone by using IDA as a chelating agent, and the reaction process of the obtained metal chelating product is as follows:
Figure DEST_PATH_IMAGE022
(2) methyl imidazole and 1, 3-propane sultone are weighed according to the molar ratio of 1:1, are added into a 250ml round-bottom flask, acetone is used as a solvent, and are electromagnetically stirred for 17 hours at the temperature of 40 ℃, so that the methyl imidazole and the 1, 3-propane sultone are subjected to condensation reaction. Stopping stirring, carrying out suction filtration to obtain a white solid, washing the sub-white solid with acetone and ethanol again, filtering to obtain white powder, drying the white powder in a vacuum drying oven at 80 ℃ for 4 hours, taking out and weighing the white powder, then acidifying the white powder with equal mass of concentrated sulfuric acid at 80 ℃ for 6 hours to obtain a transparent solution, washing the solution with a proper amount of ethyl acetate for three times, and then drying the solution for a certain time to obtain a second sulfonated ionic liquid product.
(3) Adding the obtained first metal chelate product and the second sulfonated ionic liquid product into a 250ml round-bottom flask according to the amount of the substances, reacting for 10-12h, filtering out a by-product ammonium chloride after the reaction is finished, and evaporating residual acetone, ethanol and ethyl acetate by a rotary evaporator to obtain green liquid.
(4) Dissolving the obtained green liquid in diethyl ether, filtering out residual ammonium chloride, transferring the filtrate to a separating funnel, washing for 4-6 times by using ultrapure water, detecting that no halogen ion remains, then evaporating diethyl ether by using a rotary evaporator, and drying the obtained product in vacuum for 24 hours to obtain purified ionic liquid, namely the solvent b.
The inventors have prepared several ionic liquids as shown in the following table:
Figure DEST_PATH_IMAGE023
thirdly, extracting curcumin
The components and contents of the extractants a and B used in examples 1 to 10 are shown in the following table:
Figure DEST_PATH_IMAGE024
the extraction process comprises the following steps:
(1) selecting high-quality turmeric rhizome, drying, crushing, sieving with a 80-mesh sieve, weighing a certain amount of turmeric powder, mixing with an extracting agent A in a ratio of 1 g: mixing 10ml of solid-liquid ratio, extracting for 10 hours, centrifuging at 3000-5000 rpm, using the upper filtrate for subsequent recovery, and drying the lower precipitate to obtain yellowish powder;
(2) to the obtained yellowish powder was added a 1 g: adding an extractant B into 15ml of solid-to-liquid ratio, extracting for more than 12h, filtering to obtain an extracting solution, extracting the extracting solution for 15min by using a volatile oil extraction device, centrifuging the rest extracting solution at 3000-5000 rpm, using the upper-layer filtrate for subsequent recovery, washing the lower-layer precipitate for 3 times by using deionized water, and drying to obtain the curcumin extract.
In the extraction process, the extractant A is aqueous extracting solution, and the curcumin is insoluble in water, so that the curcumin can be separated out in a precipitation form by utilizing the characteristic on the basis of fully dissolving cellulose and hemicellulose, and the separation process is simple; the extractant B is a nonpolar extracting solution, can fully extract curcumin, contains a part of ester impurities, can remove the ester impurities through distillation in the subsequent separation process, and can realize the separation of the curcumin and the ionic liquid by adopting a centrifugal method. In the process, the stability and density of the ionic liquid are high, and the ionic liquid can be separated from water or ethanol in the subsequent separation process by a simple distillation method, so that the ionic liquid can be recycled, and the requirements of environmental protection are met.
The invention adopts boron color development spectrophotometry, and the method is simple and stable and is not interfered by other yellow pigments.
Establishment of curcumin standard curve
Precisely weighing 1mg of curcumin standard substance in a 25ml measuring flask, and fixing the volume with methanol to obtain a standard solution. Accurately weighing 0.2ml, 0.3ml, 0.4ml, 0.5ml and 0.6ml of standard solution into a 10ml colorimetric cylinder, adding 3.00ml of concentrated sulfuric acid-acetic acid (1: 1), adding 1.00ml of 1.2mol/L boric acid methanol solution, shaking up, standing at room temperature for 5min, adding methanol to dilute to 10ml, carrying out colorimetric determination at 512nm respectively, and taking methanol as blank. Regression equation y =0.1269x +0.1587, r = 0.9988.
Determination of total curcumin content in curcumin
3.9994g of turmeric powder is accurately weighed in a Soxhlet extractor, and methanol extraction is carried out until turmeric is colorless. The extracting solution is added into a 100ml measuring flask to be constant volume by methanol, thus obtaining the extracting solution. Precisely measuring 0.01ml of the extract in a 10ml test tube with a plug scale, adding 3.00ml of concentrated sulfuric acid-glacial acetic acid (1: 1), adding 1.00ml of 1.2mol/L boric acid methanol solution, shaking uniformly, standing at room temperature for 5min, adding methanol to dilute to 8ml, performing colorimetric determination at 512nm respectively, and taking methanol as a blank. The curcumin content is 2.58 percent, which is the total curcumin content in the turmeric.
Determination of extraction Rate
Accurately weighing 5.00g of turmeric powder, placing the turmeric powder in an iodine measuring flask, accurately adding the schemes of the extracting agent A and the extracting agent B selected in the embodiments 1-10, and adding the curcumin extracts obtained respectively into concentrated sulfuric acid: glacial acetic acid (1: 1) 12.00ml, adding 1.2mol/L boric acid methanol solution 4.00ml, shaking, standing at room temperature for 5min, adding methanol to dilute to 32ml, performing colorimetric determination at 512nm respectively with methanol as blank, and determining curcumin extraction rate, as shown in the following table:
Figure DEST_PATH_IMAGE025
as shown in the table above, the extraction rate of curcumin finally obtained by adopting the combination of the extracting agent A and the extracting agent B can reach 84.9 percent, which is higher than about 50-70 percent in the literature, and the extraction rate of curcumin is higher. Under the extraction process, the extraction effect of the extractant A adopting the No. 1 is slightly larger than that of the extractant A adopting the No. 2 to the No. 4, and the extraction effect of the extractant B adopting the No. 5 is better than that of the extractant B adopting the No. 6; further, the reason why the extraction ratio is low in example 3 may be that the use of the ionic liquid as a whole increases the viscosity of the extractant, and the fluidity of the extractant is poor, which is disadvantageous for sufficient contact with turmeric powder.
Based on the results of the tests of examples 1 to 10, example 11 was created, which is different from example 1 in that the solid-to-liquid ratio of turmeric powder to extractant a was 1 g: 20ml of the solution; example 12 was set up, differing from example 1 in that the solid to liquid ratio of yellowish powder to extractant B was 1 g: 10ml, the curcumin extraction rates were found to be 84.5% and 84.2%, respectively, which is comparable to example 1.
Based on the detection results of the above examples 1-10, a comparative example 1 is established, which is different from example 1 in that an equal amount of ethanol is used to replace the extractant a, and the relevant extraction process is adjusted (the extraction process of ethanol is mature and is not described again); a comparative example 2 is established, and the difference from the example 1 is that the same amount of ethanol is used for replacing the extractant B, and the related extraction process is adjusted (the extraction process of ethanol is mature and is not described again); a comparative example 3 was established, which is different from example 1 in that the same amount of ethanol was used to replace the extractant a and the extractant B, respectively, and the ethanol extraction process was adjusted to be mature, and will not be described again).
The same detection method is used for detecting the comparative examples 1-3, the obtained curcumin extraction rates are 69.7%, 74.6% and 60.2% respectively, the extraction rate of the comparative example 2 is the highest, the dissolving capacity of the extractant A to cellulose is proved to be capable of fully improving the curcumin dissolution rate, the effect on improving the curcumin extraction rate is strongest, the comparative example 1 is slightly lower than the comparative example 2 but higher than the comparative example 3, and the effect on improving the curcumin extraction rate is proved to be achieved by adopting the extractant B.
The specific embodiments described herein are merely illustrative of the spirit of the invention. Various modifications or additions may be made to the described embodiments or alternatives may be employed by those skilled in the art without departing from the spirit or ambit of the invention as defined in the appended claims.

Claims (10)

1. The method for efficiently extracting curcumin is characterized by comprising the following steps of:
the method comprises the following steps: adding an extracting agent A into the crushed turmeric powder, and filtering to obtain a solid material I;
step two: adding an extracting agent B into the obtained solid material I, and filtering to remove residues to obtain an extracting solution II;
step three: centrifuging the extracting solution II, and filtering to obtain a solid material III;
step four: cleaning and drying the solid material III to obtain curcumin;
the extractant A comprises a solvent a, and the solvent a has the following structure:
Figure DEST_PATH_IMAGE001
（1）
in the formula (1), the reaction mixture is,
Figure DEST_PATH_IMAGE003
is composed of
Figure DEST_PATH_IMAGE004
、
Figure DEST_PATH_IMAGE006
、
Figure DEST_PATH_IMAGE007
、
Figure DEST_PATH_IMAGE009
、
Figure DEST_PATH_IMAGE011
One of (1);
the extractant B comprises a solvent B, and the solvent B comprises the following components:
Figure DEST_PATH_IMAGE012
（2）
in the formula (2), the reaction mixture is,
Figure DEST_PATH_IMAGE014
is metal chelating anion.
2. The method for efficiently extracting curcumin as claimed in claim 1, wherein said extractant a comprises said solvent a and deionized water, wherein the molar ratio of said solvent a to deionized water is 1-4: 1.
3. The method for efficiently extracting curcumin as claimed in claim 2, wherein the solid-to-liquid ratio of the turmeric powder to the extractant A in the first step is 1: 10-20 g/mL.
4. The method for efficiently extracting curcumin as claimed in claim 1, wherein said extractant B consists of said solvent B and absolute ethyl alcohol, wherein the volume ratio of said solvent B to said absolute ethyl alcohol is 1-4: 1.
5. The method for efficiently extracting curcumin as claimed in claim 4, wherein the solid-to-liquid ratio of the solid material I to the extractant B is 1: 10-15 g/mL.
6. The method for extracting curcumin with high efficiency as claimed in claim 1, wherein said method comprises
Figure DEST_PATH_IMAGE015
Is composed of
Figure DEST_PATH_IMAGE017
Chelate compounds, preparation of
Figure 111736DEST_PATH_IMAGE017
The chelating agent used in the chelate is one of IDA, DTPA, EDTA, NTA, HFAC and IDS.
7. The method for extracting curcumin with high efficiency as claimed in claim 6, wherein said chelating agent is one of IDA and HFAC.
8. The method for extracting curcumin with high efficiency as claimed in claim 7, wherein the preparation process of the solvent b comprises the following steps: dissolving a chelating agent into acetonitrile, adding ammonia water, sealing, stirring at room temperature, and performing primary rotary evaporation to obtain a solid; and dissolving the obtained solid in ethanol, adding copper chloride, stirring at sealed room temperature, filtering, and performing secondary rotary evaporation to obtain a first metal chelate product.
9. The method for extracting curcumin with high efficiency as claimed in claim 8, wherein the preparation process of the solvent b further comprises: mixing R-imidazole and 1, 3-propane sultone, adding acetone, stirring at 30-50 ℃, reacting to obtain a solid, acidifying the solid with concentrated acid, and washing and drying to obtain a second sulfonated ionic liquid product.
10. The method for extracting curcumin with high efficiency as claimed in claim 9, wherein the preparation process of the solvent b further comprises: and mixing the first metal chelate product and the second sulfonated ionic liquid product, reacting at sealed room temperature, filtering, performing third rotary evaporation, adding diethyl ether for dissolving, purifying, washing, performing fourth rotary evaporation, and drying to obtain a solvent b.
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CN113264817A (en) * 2021-05-26 2021-08-17 晨光生物科技集团股份有限公司 Curcumin crystallization method and application thereof
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Application publication date: 20201106