CN109942395B - Curcumin ionic liquid and application thereof - Google Patents
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Abstract
The invention discloses a biomass curcumin-based functionalized ionic liquid and application thereof. The ionic liquid is composed of curcumin structure as anion. The ionic liquid can effectively remove H2O2Active oxygen free radicals, which inhibit lipid peroxidation; the sensor is used as a multimode sensor for detecting the prohibited additive benzoyl peroxide in food safety and the energetic compound 2,4, 6-trinitrophenol in public safety; meanwhile, the invention obviously improves the problems of low solubility, poor stability, low bioavailability, large dosage of medicine and the like of curcumin, is expected to be applied to health care products, cosmetics and washing and protecting products, and improves the absorption of curcumin by human bodies.
Description
Technical Field
The invention belongs to the field of material application, and relates to curcumin ionic liquid and application thereof.
Background
Curcuma longa is a plant of the genus Curcuma of the family Zingiberaceae, and has good medicinal value. The Chinese pharmacopoeia mentioned: turmeric root is pungent, bitter and warm. Has effects in removing blood stasis, activating qi-flowing, dredging channels, and relieving pain, and can be used for treating costalgia, thoracic obstruction, cardiodynia, amenorrhea, epilepsy, rheumatic shoulder and arm pain, and traumatic injury with swelling and pain. The main chemical components of the turmeric playing pharmacological action are curcumin compounds, including curcumin, demethoxycurcumin, bisdemethoxycurcumin and the like, wherein the curcumin is the most main active component. Curcumin extracted from rhizomes of plants of Zingiberaceae such as Curcuma longa is an acidic polyphenol compound composed of two o-methylated phenols and a beta-diketone, and exists mainly in enol form in solid and liquid states. Curcumin is a pure natural yellow pigment, and is widely used in the food industry as a coloring agent, a flavoring agent and an additive. For example, curry in Indian life and barbecue rolls in the middle east region can not be used as seasonings. In addition, curcumin itself has various pharmacological actions such as anti-inflammatory, antioxidation, blood fat reduction, free radical elimination, cancer resistance, atherosclerosis resistance, obesity inhibition, aging delay and the like, and is widely concerned by medical researchers. However, curcumin has a series of problems of low solubility, poor stability, low in-vivo bioavailability, large dosage of drugs and the like, and seriously hinders the popularization and application of curcumin in the fields of food and medicines. If the solubility and stability of curcumin can be effectively increased on the premise of keeping the effect of curcumin, the utilization rate of curcumin in a living body can be greatly improved, and the unique pharmacological activity of curcumin can be exerted.
The ionic liquid is a salt which is in a liquid state at room temperature or close to room temperature, has excellent physicochemical properties such as low melting point, low volatility, high thermal stability, adjustable molecular structure, wider electrochemical window and the like, and is widely concerned at home and abroad. The neutral compound curcumin is prepared into the ionic liquid with unique properties, so that the excellent effects of the curcumin can be exerted, the unique physicochemical properties of the ionic liquid can be combined, and the defects of low solubility, poor stability and the like of the neutral compound curcumin are overcome, so that the bioavailability of the curcumin is obviously improved. The curcumin ionic liquid has the advantages of simple and rapid synthesis process, low toxicity and green synthesized product, and wide application prospect.
Free radicals are a group of highly oxidatively activated radicals produced during the metabolism of organisms, which produce a large number of Reactive Oxygen Species (ROS). In general, free radical production contributes to the benefits of regulating cell growth, inhibiting bacteria and viruses, but if there is too much free radical accumulation in the body, these oxides (e.g., H)2O2) Significant damage to the cells can occur, leading to the development of many chronic diseases such as cancer, inflammation, and the like. The two benzene rings in the molecular structure of curcumin respectively contain a phenolic hydroxyl group and a methoxyl group, and researches show that the phenolic compound with the structure has strong oxidation resistance and can play a role in removing free radicals. The curcumin ionic liquid retains the physiological activity of curcumin and has high effect on H2O2The active oxygen free radicals have stronger oxidation resistance; on the other hand, the characteristics of low melting point, non-volatility, high stability and the like of the ionic liquid are combined, the solubility, the stability and the bioavailability of the curcumin are obviously improved, and the neutral compound curcumin is greatly improved.The green curcumin ionic liquid prepared by taking natural compound amino acid as cation has strong oxidation resistance, can replace curcumin to be used as an anti-inflammatory agent, an antibacterial agent, a skin conditioner and the like to be applied to health care products and cosmetics so as to overcome the damage of excessive free radicals to human bodies.
In recent years, the social food safety incidents of China are endless, ham containing dichlorvos, nests with overproof iodine content, pork containing clenbuterol, even infant milk powder containing melamine and the like, and none of the incidents can threaten human life. Especially food additives are disputed by the broad masses: on one hand, the food additive is not added, and the food is fresh but goes bad the next day, which brings great inconvenience to the daily life of people; on the other hand, the food additive is continuously free in food, and the personal safety of consumers is threatened due to improper use of the additive. In the face of the severe situation, if green pure natural food additives can be developed or components added in the food can be strictly monitored, the problem of food safety can be effectively solved.
Disclosure of Invention
The invention aims to provide curcumin ionic liquid and application thereof.
The anion of the curcumin ionic liquid provided by the invention is curcumin anion shown in formula I, and the cation is any one of formula II to formula IV:
in the formula I, R1Is hydrogen or methoxy; r2Is hydrogen or methoxy, n ═ 1, 2 or 3;
in the formula II-formula IV, R1And R2Is a hydrocarbon group with a carbon chain length of 1 to 20, A, B and C are hydrogen or a hydrocarbon group with a carbon chain length of not more than 3 andany one of amino groups; in the definition of A, B and C, the hydrocarbyl group is specifically an alkyl group;
R3、R4、R5and R6Is hydrogen, a hydrocarbon group with a carbon chain length of 1-20 or a hydrocarbon group with a carbon chain length of 1-20 containing a substituent; the substituent is at least one of hydroxyl, ester group, amino and carboxyl;
R7are variable groups of alpha-amino acids.
Specifically, in the hydrocarbyl with the carbon chain length of 1-20 containing the substituent, the substituent is at least one of hydroxyl, ester group, amino and carboxyl;
the R is1To R6In the definition of (1), the carbon chain length is specifically a hydrocarbon group of 1 to 10; more specifically 1 to 6 hydrocarbyl groups; the hydrocarbyl is specifically an alkyl or alkoxy group; more specifically, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy and ethoxy;
the formula II can be 1-methyl-3-ethylimidazole or 1-methyl-3-butylimidazole;
the alpha-amino acid is selected from at least one of glycine, alanine, valine, leucine, isoleucine, phenylalanine, proline, tryptophan, serine, tyrosine, cysteine, methionine, asparagine, glutamine, threonine, aspartic acid, glutamic acid, lysine, arginine and histidine.
The R is7In particular to-C4H10N3、-C4H5N2、-C4H10N、-C4H11N3or-C4H6N2；
The method for preparing the curcumin ionic liquid comprises the following steps:
the curcumin and the compound corresponding to the cation are subjected to acid-base neutralization reaction to obtain the curcumin-modified cationic polymer.
Specifically, the method may include: mixing corresponding imidazolium, quaternary ammonium hydroxide or amino acid compound and curcumin in a solvent according to a certain molar ratio, stirring uniformly, and removing the solvent by rotary evaporation to obtain the final product.
In the above method, the cation corresponding compound is a hydroxide corresponding to formula II or formula III or a corresponding alpha-amino acid represented by formula IV; concretely tetraethylammonium hydroxide or tetrapropylammonium hydroxide;
the feeding molar ratio of the curcumin to the cation corresponding compound is 1: 0.5-1: 3; specifically 1: 1;
in the acid-base neutralization reaction step, the temperature is 25-80 ℃; the time is 2-36 h; in particular 8 h.
The acid-base neutralization reaction is carried out in a solvent;
the solvent is at least one selected from water, ethanol, methanol, isopropanol, acetone, acetonitrile, dichloromethane, dimethyl sulfoxide and N, N-dimethylformamide.
In addition, the application of the curcumin ionic liquid in antioxidation or antioxidant preparation, the application in at least one of curcumin health-care products, cosmetics and hair washing and caring products preparation and the application as a visual sensor also belong to the protection scope of the invention.
In addition, the application of the curcumin ionic liquid in detecting prohibited additives or benzoyl peroxide or energetic compounds or 2,4, 6-trinitrophenol also belongs to the protection scope of the invention.
The invention has the following outstanding advantages and effects:
the preparation method synthesizes curcumin ionic liquid from pure natural compound curcumin, has the advantages of low cost, green process, no pollution, pure product, simple purification, high yield, no byproduct generation and complete accordance with atom economy. The curcumin ionic liquid has the excellent properties of both curcumin and the ionic liquid, on one hand, the defects of low solubility, poor stability and the like of the curcumin are obviously improved by utilizing the characteristics of the ionic liquid, on the other hand, the ionic liquid has the pharmacological activity of the curcumin, good biocompatibility, high degradability and low biotoxicity, is expected to replace the curcumin to be applied to various fields of foods, medicines, cosmetics and the like, and improves the effect of a human body on the curcuminAbsorption of the element. The curcumin ionic liquid has strong oxidation resistance and can effectively remove H2O2Active oxygen free radicals, etc., and can be used in various fields such as food, medicine, and cosmetic; meanwhile, a choice is provided for the research and development of the natural spice type antioxidant additive. In addition, the curcumin ionic liquid has great potential application value in the field of sensors: firstly, the method can be used as a visual sensor to be applied to food safety to quickly detect the benzoyl peroxide as a banned additive; secondly, the fluorescent sensor can be used as a fluorescent sensor to be applied to specific recognition and detection of the energetic compound 2,4, 6-trinitrophenol in public safety. The sensor has the advantages of simple and convenient operation, good selectivity, high response speed and high sensitivity, and can realize the real-time detection of the benzoyl peroxide and the 2,4, 6-trinitrophenol without expensive instruments and equipment.
Detailed Description
The present invention will be further illustrated with reference to the following specific examples, but the present invention is not limited to the following examples. The method is a conventional method unless otherwise specified. The starting materials are commercially available from the open literature unless otherwise specified.
Example 1:
synthesis of tetraethyl curcumin ammonium salt ionic liquid [ N ]2222][Cur](cation: R in formula III)3、R4、R5And R6Are all-C2H5(ii) a Anion: wherein n is 1).
Adding 0.50g of curcumin into a 50mL round-bottom flask, adding 10mL of ethanol to completely dissolve the raw materials, then adding 0.80g of tetraethylammonium hydroxide aqueous solution (25%) according to the molar ratio of 1:1 of the curcumin to the tetraethylammonium hydroxide, carrying out acid-base neutralization reaction for 8h under vigorous stirring at 25 ℃, and then carrying out rotary evaporation to remove the solvent, thus obtaining the reddish brown tetraethylcurcumin ammonium salt ionic liquid.
Example 2:
synthesis of tetrapropyl curcumin ammonium salt ionic liquid [ N ]3333][Cur](cation: R in formula III)3、R4、R5And R6Are all-C3H7(ii) a Anion(s): wherein n is 1).
Adding 0.50g of curcumin into a 50mL round-bottom flask, adding 10mL of ethanol to completely dissolve the raw materials, then adding 1.3g of tetrapropyl ammonium hydroxide aqueous solution (25%) according to the molar ratio of 1:1 of curcumin to tetrapropyl ammonium hydroxide, carrying out acid-base neutralization reaction for 8h under vigorous stirring at 25 ℃, and then removing the solvent by rotary evaporation to obtain the reddish brown tetrapropyl curcumin ammonium salt ionic liquid.
Example 3:
synthesis of tetrabutylcurcumin ammonium salt ionic liquid [ N ]4444][Cur](cation: R in formula III)3、R4、R5And R6Are all-C4H9(ii) a Anion: wherein n is 1).
Dissolving 0.50g of tetrabutyl bromide salt in a round-bottom flask containing about 20mL of ethanol or isopropanol, adding 0.12g of potassium hydroxide according to the molar ratio of 1:1.05, mixing and stirring for 1 hour, filtering to remove white precipitated potassium bromide, slowly adding 0.57g of curcumin, violently stirring at 25 ℃ for acid-base neutralization reaction for 8 hours, and removing the solvent by rotary evaporation to obtain the reddish brown tetrabutyl curcumin ammonium salt ionic liquid.
Example 4:
synthesis of 1-methyl-3-ethylimidazole curcumin salt ionic liquid [ C ]2mim][Cur](cation: R in formula II)1is-CH3，R2is-C2H5(ii) a A. B and C are hydrogen; anion: wherein n is 1).
Dissolving 0.34g of 1-methyl-3-ethylimidazole bromine salt in a round-bottom flask with 15mL of ethanol or isopropanol, adding 0.12g of potassium hydroxide according to the molar ratio of 1:1.05, mixing and stirring for 1h, removing white precipitated potassium bromide by suction filtration, slowly adding 0.57g of curcumin, carrying out acid-base neutralization reaction at 25 ℃ under vigorous stirring for 16h, and removing the solvent by rotary evaporation to obtain the dark green 1-methyl-3-ethylimidazole curcumin salt ionic liquid.
Example 5:
synthesis of 1-methyl-3-butylimidazole curcumin salt Ionic liquid [ C4mim][Cur](cation: R in formula II)1is-CH3，R2is-C4H9(ii) a A. B and C are hydrogen; anion: wherein n is 1).
Dissolving 0.35g of 1-methyl-3-ethylimidazole bromine salt in a round-bottom flask with 15mL of ethanol or isopropanol, adding 0.13g of potassium hydroxide according to the molar ratio of 1:1.05, mixing and stirring for 1 hour, removing white precipitated potassium bromide by suction filtration, slowly adding 0.59g of curcumin, carrying out acid-base neutralization reaction at 25 ℃ under vigorous stirring for 16 hours, and removing the solvent by rotary evaporation to obtain the dark green 1-methyl-3-butylimidazole curcumin salt ionic liquid.
Example 6:
synthesis of choline-based curcumin salt ionic liquids [ Ch][Cur](cation: R in formula III)3、R4And R5Are all-CH3，R6is-C2H5O; anion: wherein n is 1).
Adding 0.50g of curcumin into a 50mL round-bottom flask, adding 10mL of ethanol to completely dissolve the raw materials, adding 0.33g of choline aqueous solution (50%) according to the molar ratio of the curcumin to the choline of 1:1, carrying out acid-base neutralization reaction for 8h under vigorous stirring at 25 ℃, and then removing the solvent by rotary evaporation to obtain the reddish-brown choline curcumin salt ionic liquid.
Example 7:
synthesis of arginine-based curcumin salt ionic liquid [ Arg ]][Cur](cation: R in formula IV)7is-C4H10N3(ii) a Anion: wherein n is 1).
Adding 0.50g of curcumin into a 50mL round-bottom flask, adding 10mL of ethanol to completely dissolve the raw materials, adding 0.24g of arginine according to the molar ratio of the curcumin to the arginine of 1:1, carrying out acid-base neutralization reaction for 8h under vigorous stirring at 25 ℃, and then carrying out rotary evaporation to remove the solvent to obtain brick-red arginine curcumin salt ionic liquid.
Example 8:
synthesis of histidine-based curcumin salt ionic liquid [ His][Cur](cation: R in formula IV)7is-C4H5N2(ii) a Anion: wherein n is 1).
Adding 0.50g of curcumin into a 50mL round-bottom flask, adding 10mL of ethanol to completely dissolve the raw materials, adding 0.22g of histidine according to the molar ratio of the curcumin to the histidine of 1:1, carrying out acid-base neutralization reaction at 25 ℃ by vigorous stirring for 8h, and then carrying out rotary evaporation to remove the solvent, thus obtaining the brick-red histidine curcumin salt ionic liquid.
Example 9:
synthesis of lysine-based curcumin salt Ionic liquids [ Lys][Cur](cation: R in formula IV)7is-C4H10N; anion: wherein n is 1).
Adding 0.50g of curcumin into a 50mL round-bottom flask, adding 10mL of ethanol to completely dissolve the raw materials, adding 0.20g of histidine according to the molar ratio of the curcumin to the lysine of 1:1, carrying out acid-base neutralization reaction for 8h under vigorous stirring at 25 ℃, and then carrying out rotary evaporation to remove the solvent to obtain brick-red lysine curcumin salt ionic liquid.
Example 10:
synthesis of arginine-based curcumin salt ionic liquid [ Arg ]][Cur]2(cation: R in formula IV)7is-C4H11N3(ii) a Anion: wherein n is 1).
Adding 0.50g of curcumin into a 50mL round-bottom flask, adding 10mL of ethanol to completely dissolve the raw materials, adding 0.48g of arginine according to the molar ratio of the curcumin to the arginine of 2:1, carrying out acid-base neutralization reaction at 25 ℃ by vigorous stirring for 24h, and then carrying out rotary evaporation to remove the solvent to obtain brick-red arginine curcumin salt ionic liquid.
Example 11:
synthesis of histidine-based curcumin salt ionic liquid [ His][Cur]2(cation: R in formula IV)7is-C4H6N2(ii) a Anion: wherein n is 1).
Adding 0.50g of curcumin into a 50mL round-bottom flask, adding 10mL of ethanol to completely dissolve the raw materials, adding 0.44g of histidine according to the molar ratio of the curcumin to the histidine of 2:1, carrying out acid-base neutralization reaction at 25 ℃ under vigorous stirring for 24h, and then carrying out rotary evaporation to remove the solvent, thus obtaining the brick-red histidine curcumin salt ionic liquid.
Example 12:
example 6 Choline curcumin salt Ionic liquid obtained scavenges H2O2Experiment of free radicals.
Ak, et al, analytical and radial sampling properties of current, chemical-Biological Interactions 174(2008) 27-37]Removing H from curcumin2O2Introduction method of free radical, ultraviolet-visible spectrophotometry for determining curcumin ionic liquid scavenging H2O2The ability of free radicals.
In 5mL of H with a concentration of 50mmol/L2O2Adding 20uL of choline curcumin salt ionic liquid with mass concentration of 0.50mg/mL into the solution (prepared by phosphoric acid buffer solution with pH of 6.86), and measuring the absorbance value A of the solution at 217nm by using the phosphoric acid buffer solution as references. Simultaneous assay of 20uL of solvent with 5mL of H2O2Absorbance value A ofc. And finally, the clearance rate of the ionic liquid to the free radicals is calculated according to the formula:
(1-A) in the form of a powders/Ac)×100
Wherein A iscIs H when no curcumin ionic liquid is added2O2Absorbance value of AsFor adding curcumin ionic liquid H2O2The absorbance value of (a).
The choline curcumin salt ionic liquid pair H is obtained by calculation2O2The clearance rate of free radicals is 50 percent and is much higher than that of vitamin C (29 percent), which indicates that the antioxidant capacity of the vitamin C is stronger than that of the vitamin C. It is thus seen that the choline curcumin salt ionic liquid can effectively eliminate H2O2Active oxygen free radicals have strong oxidation resistance, can be effectively used as a natural spice type oxidation resistance additive to be applied to the food industry, and promote the development of the green food industry.
Example 13:
example 7 shampoo experiments based on arginine curcumin salt ionic liquid.
The shampoo comprises the following components in percentage by weight: panthenol (0.2%), sodium lauryl sulfate (15%), sodium laureth sulfate (4%), cocamidopropyl betaine (5%), sodium citrate (1%), citric acid (1%), cocamide (8%), cocamido amine oxide (0.5%), polydimethylsiloxane (3%), sodium chloride (0.5%), ethylene glycol distearate (1%), curcumin ionic liquid (10%), essence (0.5%) and the balance of distilled water.
According to the raw material percentage, firstly, respectively and quantitatively weighing 0.040g of panthenol, 3.0g of sodium lauryl sulfate, 0.80g of sodium laureth sulfate, 1.0g of cocamidopropyl betaine, 0.20g of sodium citrate, 0.20g of citric acid, 1.6g of cocamide, 0.10g of cocamidoamine oxide, 0.60g of polydimethylsiloxane, 0.10g of sodium chloride and 0.20g of ethylene glycol distearate in two 50mL volumetric flasks marked with A, B numbers, adding 10mL of distilled water, heating and stirring at 60-70 ℃ until the materials are completely dissolved; then when the solution is cooled to 25 ℃, 0.10g of essence is added into the solution A, 2.0g of arginine curcumin salt ionic liquid and 0.10g of essence are added into the solution B, and the mixture is stirred and mixed evenly to obtain the simple shampoo; and (3) uniformly smearing A, B two shampoos on the surface of a dried hair sample at normal temperature, and performing SEM scanning test analysis after 3-5 min.
The analysis result shows that compared with the hair samples of the shampoo A without the amino acid curcumin salt ionic liquid, the hair samples of the shampoo B with the ionic liquid have wider film coverage area, lower hair quality surface roughness and no obvious wrinkles in SEM images.
Example 14:
the visual sensor of the tetrapropyl curcumin ammonium salt ionic liquid obtained in the example 2 is applied to an experiment for detecting benzoyl peroxide in food safety.
0.50g of benzoyl peroxide is quantitatively weighed and added into 10mL of ethanol solution of tetrapropyl curcumin ammonium salt ionic liquid with the concentration of 0.10mmol/L, the mixture is vigorously shaken and is placed for 20min at room temperature, and the color of the ionic liquid solution is observed to be changed from reddish brown to colorless. Simultaneously weighing the same amount of other interference substances such as glycine, glutamic acid, lysine, glucose and KCl、NaCl、CaCl2、NaNO3When the ionic liquid solution is added into 10mL of ionic liquid solution with the same concentration, the color of the ionic liquid solution is not obviously changed. These solutions were then placed under an ultraviolet lamp (365nm) for comparative observation and the solution with only benzoyl peroxide added was quenched for fluorescence, while the other interferent solutions were not evident. Therefore, the tetrapropyl curcumin ammonium salt ionic liquid can be directly used as a visual sensor for selectively detecting benzoyl peroxide.
Example 15:
a fluorescence sensor of 1-methyl-3-ethylimidazole curcumin salt ionic liquid is applied to an experiment for detecting 2,4, 6-trinitrophenol in public safety.
Quantitatively weighing 0.20g of trinitrophenol, adding the trinitrophenol into 10mL of ethanol solution of 1-methyl-3-ethylimidazole curcumin salt ionic liquid with the concentration of 0.10mmol/L, violently oscillating, standing for 5min at room temperature, and then placing the solution and 10mL of 1-methyl-3-ethylimidazole curcumin ammonium salt ionic liquid with the same concentration under an ultraviolet lamp (365nm) for comparative observation, wherein the fluorescence of the solution added with the trinitrophenol is obviously enhanced. As can be seen, the 1-methyl-3-ethylimidazole curcumin salt ionic liquid can be used as a fluorescence sensor for detecting the energetic compound 2,4, 6-trinitrophenol.
Claims (8)
1. The application of curcumin ionic liquid as a visual sensor;
the visual sensor is used for detecting benzoyl peroxide or 2,4, 6-trinitrophenol;
the anion of the curcumin ionic liquid is curcumin anion shown in formula I, and the cation is any one of formula II to formula III:
in the formula I, R1Is hydrogen or methoxy; r2Is hydrogen or methoxy, n ═ 1, 2 or 3;
in the formula II-formula III, R1And R2The alkyl or alkoxy with the carbon chain length of 1-10, A, B and C are hydrogen or any one of alkyl and amino with the carbon chain length of not more than 3;
R3、R4、R5and R6Is hydrogen, alkyl or alkoxy with carbon chain length of 1-10, or alkyl or alkoxy with carbon chain length of 1-10 containing substituent;
in the alkyl or alkoxy with the carbon chain length of 1-10, the substituent is at least one of hydroxyl, ester, amino and carboxyl.
2. An application of curcumin ionic liquid in detecting benzoyl peroxide or 2,4, 6-trinitrophenol;
the anion of the curcumin ionic liquid is curcumin anion shown in formula I, and the cation is any one of formula II to formula III:
in the formula I, R1Is hydrogen or methoxy; r2Is hydrogen or methoxy, n ═ 1, 2 or 3;
in the formula II-formula III, R1And R2The alkyl or alkoxy with the carbon chain length of 1-10, A, B and C are hydrogen or any one of alkyl and amino with the carbon chain length of not more than 3;
R3、R4、R5and R6Is hydrogen, alkyl or alkoxy with carbon chain length of 1-10, or alkyl or alkoxy with carbon chain length of 1-10 containing substituent；
In the alkyl or alkoxy with the carbon chain length of 1-10, the substituent is at least one of hydroxyl, ester, amino and carboxyl.
3. Use according to claim 1 or 2, characterized in that: the preparation method of the curcumin ionic liquid comprises the following steps:
the curcumin and the compound corresponding to the cation are subjected to acid-base neutralization reaction to obtain the curcumin-modified cationic polymer.
4. Use according to claim 3, characterized in that: the cation corresponding compound is hydroxide corresponding to formula II or formula III.
5. Use according to claim 3, characterized in that: the feeding molar ratio of the curcumin to the cation corresponding compound is 1: 0.5-1: 3;
in the acid-base neutralization reaction step, the temperature is 25-80 ℃; the time is 2-36 h.
6. Use according to claim 5, characterized in that: the feeding molar ratio of the curcumin to the cation corresponding compound is 1:1.
7. Use according to claim 3, characterized in that: the acid-base neutralization reaction is carried out in a solvent.
8. Use according to claim 7, characterized in that: the solvent is at least one selected from water, ethanol, methanol, isopropanol, acetone, acetonitrile, dichloromethane, dimethyl sulfoxide and N, N-dimethylformamide.
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Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009144220A1 (en) * | 2008-05-29 | 2009-12-03 | Universite Libre De Bruxelles | Water soluble curcumin compositions for use in anti-cancer and anti-inflammatory therapy |
| CN104371111A (en) * | 2014-10-20 | 2015-02-25 | 江南大学 | Fluorescence chemical sensor for detecting 2,4,6-trinitrophenol and preparation method of fluorescence chemical reactor |
| CN105287289A (en) * | 2015-11-17 | 2016-02-03 | 深圳市优源生物科技有限公司 | Hair-loss-preventing hair-growing curcumin shampoo |
| CN105311004A (en) * | 2015-05-06 | 2016-02-10 | 江苏靶标生物医药研究所有限公司 | Curcumin and application of pharmaceutical salt thereof |
| CN105348219A (en) * | 2014-08-22 | 2016-02-24 | 沈阳药科大学 | Curcumin analogues and preparation and application thereof |
| CN107200787A (en) * | 2017-05-23 | 2017-09-26 | 四川大学 | A kind of imidazoles alginate ionic liquid and its synthetic method |
| CN108697601A (en) * | 2017-09-05 | 2018-10-23 | 拉芳家化股份有限公司 | A kind of cosmetic composition containing antioxidant |
| CN108741050A (en) * | 2018-08-29 | 2018-11-06 | 李涛 | A kind of health products and preparation method thereof |
-
2019
- 2019-03-29 CN CN201910247553.XA patent/CN109942395B/en active Active
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009144220A1 (en) * | 2008-05-29 | 2009-12-03 | Universite Libre De Bruxelles | Water soluble curcumin compositions for use in anti-cancer and anti-inflammatory therapy |
| CN105348219A (en) * | 2014-08-22 | 2016-02-24 | 沈阳药科大学 | Curcumin analogues and preparation and application thereof |
| CN104371111A (en) * | 2014-10-20 | 2015-02-25 | 江南大学 | Fluorescence chemical sensor for detecting 2,4,6-trinitrophenol and preparation method of fluorescence chemical reactor |
| CN105311004A (en) * | 2015-05-06 | 2016-02-10 | 江苏靶标生物医药研究所有限公司 | Curcumin and application of pharmaceutical salt thereof |
| CN105287289A (en) * | 2015-11-17 | 2016-02-03 | 深圳市优源生物科技有限公司 | Hair-loss-preventing hair-growing curcumin shampoo |
| CN107200787A (en) * | 2017-05-23 | 2017-09-26 | 四川大学 | A kind of imidazoles alginate ionic liquid and its synthetic method |
| CN108697601A (en) * | 2017-09-05 | 2018-10-23 | 拉芳家化股份有限公司 | A kind of cosmetic composition containing antioxidant |
| CN108741050A (en) * | 2018-08-29 | 2018-11-06 | 李涛 | A kind of health products and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| 姜黄素类化合物的提纯及性能研究;孙鹏尧;《中国知网》;20161231 * |
| 高效液相色谱法测定保健品中姜黄素含量的研究;单胜艳等;《饮料工业》;20141231;第17卷(第2期);第24-26页 * |
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