CN113214332A - Water-soluble compound based on naringin and preparation method thereof - Google Patents
Water-soluble compound based on naringin and preparation method thereof Download PDFInfo
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Abstract
The invention provides a water-soluble compound based on naringin and a preparation method thereof, belonging to the technical field of compound synthesis. The compound has a structure shown in a formula (1). The invention also provides a preparation method of the water-soluble compound based on naringin, which comprises the steps of taking allyl bromide as a double-bond modifier, taking phenolic hydroxyl in a molecular structure of the biologically-based material naringin as a modification site, carrying out double-bond modification under an alkaline condition to prepare a double-bond modified naringin compound, and then taking the double-bond modified naringin compound as a raw material, and epoxidizing double bonds by using peroxide to prepare the water-soluble epoxidized naringin. The compound has the advantages of low preparation cost and simple operation due to excellent water solubility, and has good industrial application value.
Description
Technical Field
The invention belongs to the technical field of compound synthesis, and particularly relates to a water-soluble compound based on naringin and a preparation method thereof.
Background
The flavonoid compounds are plant secondary metabolites, widely exist in natural plants, exist in free states or are combined with sugar into glycoside forms, and are not only numerous, but also complex and various in chemical structure. Flavonoid glycosides are generally readily soluble in solvents with strong polarity such as water, ethanol, and methanol, and the longer the sugar chain, the better the water solubility. The flavonoid glycoside compounds mostly contain phenolic hydroxyl groups, so that the flavonoid glycoside compounds have wide application prospects in the field of material science.
The main compound in pericarpium Citri Grandis is naringin, which is a natural flavanone compound existing in Rutaceae Citrus plants such as semen Lepidii, and has pharmacological effects of resisting bacteria, diminishing inflammation, resisting cancer, resisting mutation, lowering blood pressure, reducing blood cholesterol and thrombosis. The naringin has a structure comprising phenolic hydroxyl and disaccharide, so that the naringin has a good application prospect in the fields of food, medicine and industry, but the naringin is difficult to apply industrially due to low solubility in water.
Disclosure of Invention
The invention aims to provide a water-soluble compound based on naringin and a preparation method thereof, wherein the compound has good water solubility.
In order to achieve the purpose, the technical scheme adopted by the invention comprises the following steps:
the invention firstly provides a water-soluble compound based on naringin, which has a structure shown in a formula (1):
the invention also provides a preparation method of the water-soluble compound based on naringin, which comprises the following steps:
the method comprises the following steps: preparation of double bond modified naringin
Dissolving naringin, alkali, a modifier and a phase transfer catalyst in a solvent for reaction to obtain double-bond modified naringin;
step two: preparation of water-soluble compounds
And (3) reacting the double-bond modified naringin obtained in the step one with peroxide in an ice bath, and then heating for reaction to obtain the water-soluble compound based on naringin.
Preferably, the molar ratio of the phenolic hydroxyl group of the naringin to the modifier in the first step is 1: (1-3), the molar ratio of the alkali to the modifier is 1: (1-2), the molar ratio of the phase transfer catalyst to the base is 1: (20-30).
Preferably, the reaction temperature of the first step is 30-60 ℃, and the reaction time is 12-48 h.
Preferably, the modifier in the first step is allyl chloride or allyl bromide;
preferably, the alkali in the first step is K2CO3,Na2CO3,BaCO3Or MgCO3。
Preferably, the phase transfer catalyst in the first step is at least one of benzyltriethylammonium chloride (TEBAC), tetrabutylammonium bromide (TBAB), tetrabutylammonium chloride, tetrabutylammonium hydrogen sulfate, trioctylmethylammonium chloride, dodecyltrimethylammonium chloride or tetradecyltrimethylammonium chloride.
Preferably, in the second step, the molar ratio of the double-bond modified naringin to the peroxide is 1: (1-3).
Preferably, the heating reaction temperature of the second step is 10-40 ℃, and the reaction time is 24-96 h.
Preferably, in the second step, the peroxide is one or more of hydrogen peroxide, peracetic acid and m-chloroperoxybenzoic acid.
The invention has the advantages of
The invention provides a water-soluble compound based on naringin and a preparation method thereof, wherein the water-soluble compound has a structure shown in a formula (1); the compound takes allyl bromide as a double-bond modifier, takes phenolic hydroxyl in a bio-based material naringin molecular structure as a modification site, carries out double-bond modification under an alkaline condition to prepare a double-bond modified naringin compound, and then takes the double-bond modified naringin compound as a raw material to prepare water-soluble epoxidized naringin by epoxidizing double bonds with peroxide. According to the invention, epoxy chloropropane is avoided by means of peroxide epoxidation after double bonds are grafted, in order to keep the original glycoside structure from being damaged, when the double bonds are grafted, the hydroxyl in the glycoside is protected by using weak base, and meanwhile, the original phenolic hydroxyl is grafted with double bonds and epoxidized to obtain a compound with excellent water solubility.
Drawings
FIG. 1 is an infrared spectrum of a water-soluble naringin-based epoxy resin of formula (1) prepared in example 1 of the present invention.
FIG. 2 is the nuclear magnetic resonance hydrogen spectrum of the water-soluble epoxy resin based on naringin shown in formula (1) prepared in example 1 of the present invention.
Detailed Description
The invention firstly provides a water-soluble compound based on naringin, which has a structure shown in a formula (1):
the invention also provides a preparation method of the water-soluble compound based on naringin, which comprises the following steps:
the method comprises the following steps: preparation of double bond modified naringin
Dissolving naringin, alkali, a modifier and a phase transfer catalyst in a solvent for reaction to obtain double-bond modified naringin;
according to the invention, the molar ratio of the phenolic hydroxyl group of the naringin to the modifier is preferably 1: (1-3), the ratio of the molar mass of base to the molar mass of modifier is preferably 1: (1-2), the molar mass ratio of the phase transfer catalyst to the base is preferably 1: (20-30). The reaction time is preferably 12h-48 h; the reaction temperature is preferably 30-60 ℃; after the reaction is finished, preferably filtering to remove solid precipitate, performing rotary evaporation on the filtrate to remove the solvent to obtain a dry solid, washing with anhydrous ethanol for 1-3 times, and finally drying to obtain double-bond modified naringin;
according to the invention, the modifier is preferably allyl chloride or allyl bromide; the alkali is preferably K2CO3,Na2CO3,BaCO3Or MgCO3(ii) a The phase transfer catalyst is preferably at least one of benzyltriethylammonium chloride (TEBAC), tetrabutylammonium bromide (TBAB), tetrabutylammonium chloride, tetrabutylammonium hydrogen sulfate, trioctylmethylammonium chloride, dodecyltrimethylammonium chloride or tetradecyltrimethylammonium chloride. The solvent used is preferably one or more of acetone, N Dimethylformamide (DMF), water, methanol, ethanol, dichloromethane, chloroform, ethyl acetate, and dimethyl sulfoxide, and more preferably a mixed solvent of ethanol and water or a mixed solvent of DMF and water.
Step two: preparation of water-soluble compounds
And (3) reacting the double-bond modified naringin obtained in the step one with peroxide in an ice bath, and then heating for reaction to obtain the water-soluble compound based on naringin.
According to the invention, the double bond modified naringin obtained in the first step and peroxide are dissolved in a solvent, firstly reacted in an ice bath, the ice bath reaction temperature is preferably 0 ℃, the reaction time is preferably 1-3h, then the reaction is carried out by heating, the reaction temperature is preferably 10-40 ℃, the reaction time is preferably 24-96 h, and the molar ratio of the double bond and the peroxide of the product in the first step is preferably 1: (1-3), after the reaction is finished, preferably filtering to remove solid precipitate, performing rotary evaporation on the filtrate to remove the solvent to obtain a dry solid, washing with pure water, collecting an aqueous phase, performing rotary evaporation on the aqueous phase to remove the solvent to obtain the dry solid, dissolving the product in water, removing insoluble substances, drying, repeating for 1-3 times, and finally drying the filtrate to obtain the water-soluble compound.
According to the invention, the peroxide is preferably one or more of hydrogen peroxide, peracetic acid and m-chloroperoxybenzoic acid. The solvent is preferably one or more of acetone, N-Dimethylformamide (DMF), water, methanol, ethanol, dichloromethane, chloroform, ethyl acetate, and dimethyl sulfoxide.
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto.
Example 1
(1)40g of naringin, 37.6g of potassium carbonate, 2.164g of benzyltriethylammonium chloride and 23.6ml of allyl bromide were charged into 400ml of ethanol: water 9: 1, heating to 50 ℃, and reacting for 24 hours to obtain the double-bond modified naringin solution. After the reaction is finished, filtering to remove solid precipitate, removing the solvent from the filtrate to obtain dry solid, washing with anhydrous ethanol for 3 times, repeatedly filtering to remove the solid precipitate, and finally drying the filtrate to obtain the double-bond modified naringin.
(2) And (2) putting 40g of the product obtained in the step (1) and 31.36g of m-chloroperoxybenzoic acid into 400ml of ethanol solvent together, reacting in an ice-water bath at 0 ℃ for 2 hours, and then heating to room temperature for reacting for 46 hours to obtain a solution of the water-soluble compound based on the naringin. After the reaction was completed, the solid precipitate was removed by filtration, the solvent was removed from the filtrate to obtain a dry solid, which was washed 3 times with 400ml of pure water, the aqueous phase was collected, and the aqueous phase was rotary-evaporated to obtain a dry solid. Dissolving with 100ml water, filtering to remove insoluble substances, repeating for 3 times, and drying the filtrate to obtain naringin-based water-soluble compound solid. The yield was 94.5%
FIG. 1 is a NMR spectrum of a product prepared in example 1 of the present invention. FIG. 2 is an infrared spectrum of the product produced in example 1 of the present invention. Fig. 1 and fig. 2 illustrate that the present invention successfully synthesized naringin-based water-soluble compounds.
The product obtained in example 1 was tested and measured for solubility of 1.399g/ml at 20 ℃ and naringin solubility of 1mg/ml according to GB/T21845-2008 flask method.
Example 2
(1)40g of naringin, 18.8g of potassium carbonate, 1.08g of benzyltriethylammonium chloride and 11.8ml of allyl bromide were charged into 400ml of ethanol: water 9: 1, heating to 50 ℃, and reacting for 24 hours to obtain the double-bond modified naringin solution. After the reaction is finished, filtering to remove solid precipitate, removing the solvent from the filtrate to obtain dry solid, washing with anhydrous ethanol for 3 times, repeatedly filtering to remove the solid precipitate, and finally drying the filtrate to obtain the double-bond modified naringin.
(2) And (2) putting 40g of the product obtained in the step (1) and 31.36g of m-chloroperoxybenzoic acid into 400ml of ethanol solvent together, reacting in an ice-water bath at 0 ℃ for 2 hours, and then heating to room temperature for reacting for 46 hours to obtain a solution of the water-soluble compound based on the naringin. After the reaction was completed, the solid precipitate was removed by filtration, the solvent was removed from the filtrate to obtain a dry solid, which was washed 3 times with 400ml of pure water, the aqueous phase was collected, and the aqueous phase was rotary-evaporated to obtain a dry solid. Dissolving with 100ml water, filtering to remove insoluble substances, repeating for 3 times, and drying the filtrate to obtain naringin-based water-soluble compound solid. The yield is 90.3 percent
The product obtained in example 2 was tested according to the method of example 1, having a solubility of 1.155g/ml at 20 ℃.
Example 3
(1)40g of naringin, 37.6g of potassium carbonate, 2.164g of benzyltriethylammonium chloride and 23.6ml of allyl bromide were charged into 400ml of ethanol: water-8: 2, heating to 50 ℃, and reacting for 24 hours to obtain the double-bond modified naringin solution. After the reaction is finished, filtering to remove solid precipitate, removing the solvent from the filtrate to obtain dry solid, washing with anhydrous ethanol for 3 times, repeatedly filtering to remove the solid precipitate, and finally drying the filtrate to obtain the double-bond modified naringin.
(2) And (2) putting 40g of the product obtained in the step (1) and 62.75g of m-chloroperoxybenzoic acid into 400ml of ethanol solvent together, reacting in an ice-water bath at 0 ℃ for 2 hours, and then heating to room temperature for reacting for 46 hours to obtain a solution of the water-soluble compound based on the naringin. After the reaction was completed, the solid precipitate was removed by filtration, the solvent was removed from the filtrate to obtain a dry solid, which was washed 3 times with 400ml of pure water, the aqueous phase was collected, and the aqueous phase was rotary-evaporated to obtain a dry solid. Dissolving with 100ml water, filtering to remove insoluble substances, repeating for 3 times, and drying the filtrate to obtain naringin-based water-soluble compound solid. The yield was 91.2%
The product obtained in example 3 was tested according to the procedure in example 1 and had a solubility of 1.289g/ml at 20 ℃.
Example 4
(1)40g of naringin, 37.6g of potassium carbonate, 2.164g of benzyltriethylammonium chloride and 23.6ml of allyl bromide are charged into 400ml of ethanol: water 7: 3, heating to 50 ℃, and reacting for 24 hours to obtain the double-bond modified naringin solution. After the reaction is finished, filtering to remove solid precipitate, removing the solvent from the filtrate to obtain dry solid, washing with anhydrous methanol for 3 times, repeatedly filtering to remove the solid precipitate, and finally drying the filtrate to obtain the double-bond modified naringin.
(2) And (2) putting 40g of the product obtained in the step (1) and 31.36g of m-chloroperoxybenzoic acid into 400ml of methanol solvent together, reacting in an ice-water bath at 0 ℃ for 2 hours, and then heating to room temperature for reacting for 46 hours to obtain a solution of the water-soluble compound based on the naringin. After the reaction was completed, the solid precipitate was removed by filtration, the solvent was removed from the filtrate to obtain a dry solid, which was washed 3 times with 400ml of pure water, the aqueous phase was collected, and the aqueous phase was rotary-evaporated to obtain a dry solid. Dissolving with 100ml water, filtering to remove insoluble substances, repeating for 3 times, and drying the filtrate to obtain naringin-based water-soluble compound solid. The yield was 93.3%
The product obtained in example 4 was tested according to the method of example 1, having a solubility of 1.325g/ml at 20 ℃.
Example 5
(1)40g of naringin, 37.6g of potassium carbonate, 2.164g of benzyltriethylammonium chloride and 23.6ml of allyl bromide are charged into 400ml of ethanol: water 7: 3, heating to 50 ℃, and reacting for 24 hours to obtain the double-bond modified naringin solution. After the reaction is finished, filtering to remove solid precipitate, removing the solvent from the filtrate to obtain dry solid, washing with anhydrous methanol for 3 times, repeatedly filtering to remove the solid precipitate, and finally drying the filtrate to obtain the double-bond modified naringin.
(2) And (2) putting 40g of the product obtained in the step (1) and 31.36g of m-chloroperoxybenzoic acid into 400ml of methanol solvent together, reacting in an ice-water bath at 0 ℃ for 2 hours, and then heating to room temperature for reacting for 70 hours to obtain a solution of the water-soluble compound based on the naringin. After the reaction was completed, the solid precipitate was removed by filtration, the solvent was removed from the filtrate to obtain a dry solid, which was washed 3 times with 400ml of pure water, the aqueous phase was collected, and the aqueous phase was rotary-evaporated to obtain a dry solid. Dissolving with 100ml water, filtering to remove insoluble substances, repeating for 3 times, and drying the filtrate to obtain naringin-based water-soluble compound solid. The yield was 91.7%
The product obtained in example 5 was tested according to the method of example 1, having a solubility of 1.226g/ml at 20 ℃.
Example 6
(1)40g of naringin, 37.6g of potassium carbonate, 2.164g of benzyltriethylammonium chloride and 23.6ml of allyl bromide are charged into 400ml of ethanol: water 7: 3, heating to 50 ℃, and reacting for 48 hours to obtain the double-bond modified naringin solution. After the reaction is finished, filtering to remove solid precipitate, removing the solvent from the filtrate to obtain dry solid, washing with anhydrous methanol for 3 times, repeatedly filtering to remove the solid precipitate, and finally drying the filtrate to obtain the double-bond modified naringin.
(2) And (2) putting 40g of the product obtained in the step (1) and 31.36g of m-chloroperoxybenzoic acid into 400ml of methanol solvent together, reacting in an ice-water bath at 0 ℃ for 2 hours, and then heating to room temperature for reacting for 70 hours to obtain a solution of the water-soluble compound based on the naringin. After the reaction was completed, the solid precipitate was removed by filtration, the solvent was removed from the filtrate to obtain a dry solid, which was washed 3 times with 400ml of pure water, the aqueous phase was collected, and the aqueous phase was rotary-evaporated to obtain a dry solid. Dissolving with 100ml water, filtering to remove insoluble substances, repeating for 3 times, and drying the filtrate to obtain naringin-based water-soluble compound solid. The yield was 93.8%
The product obtained in example 6 was tested according to the method of example 1, with a solubility of 1.319g/ml at 20 ℃.
Example 7
(1)40g of naringin, 37.6g of potassium carbonate, 2.164g of benzyltriethylammonium chloride and 23.6ml of allyl bromide are charged to 400ml of DMF: water 7: 3, heating to 50 ℃, and reacting for 48 hours to obtain the double-bond modified naringin solution. After the reaction is finished, filtering to remove solid precipitate, removing the solvent from the filtrate to obtain dry solid, washing with DMF for 3 times, repeatedly filtering to remove solid precipitate, and finally drying the filtrate to obtain the double-bond modified naringin.
(2) And (2) putting 40g of the product obtained in the step (1) and 31.36g of m-chloroperoxybenzoic acid into 400ml of methanol solvent together, reacting in an ice-water bath at 0 ℃ for 2 hours, and then heating to room temperature for reacting for 70 hours to obtain a solution of the water-soluble compound based on the naringin. After the reaction was completed, the solid precipitate was removed by filtration, the solvent was removed from the filtrate to obtain a dry solid, which was washed 3 times with 400ml of pure water, the aqueous phase was collected, and the aqueous phase was rotary-evaporated to obtain a dry solid. Dissolving with 100ml water, filtering to remove insoluble substances, repeating for 3 times, and drying the filtrate to obtain naringin-based water-soluble compound solid. The yield was 94.2%
The product obtained in example 7 was tested according to the method of example 1 and had a solubility of 1.343g/ml at 20 ℃.
Although the present invention has been described with reference to a few preferred embodiments, it should be understood that various changes and modifications can be made therein by those skilled in the art without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (10)
1. A naringin-based water-soluble compound, characterized by having a structure represented by formula (1):
2. the preparation method of the water-soluble naringin-based compound as claimed in claim 1, comprising the steps of:
the method comprises the following steps: preparation of double bond modified naringin
Dissolving naringin, alkali, a modifier and a phase transfer catalyst in a solvent for reaction to obtain double-bond modified naringin;
step two: preparation of water-soluble compounds
And (3) reacting the double-bond modified naringin obtained in the step one with peroxide in an ice bath, and then heating for reaction to obtain the water-soluble compound based on naringin.
3. The preparation method of the water-soluble compound based on the naringin, according to the claim 2, wherein the molar ratio of the phenolic hydroxyl group of the naringin to the modifier in the first step is 1: (1-3), the molar ratio of the alkali to the modifier is 1: (1-2), the molar ratio of the phase transfer catalyst to the base is 1: (20-30).
4. The preparation method of the water-soluble naringin-based compound as claimed in claim 2, wherein the reaction temperature in the first step is 30-60 ℃ and the reaction time is 12-48 h.
5. The method for preparing the water-soluble naringin-based compound as claimed in claim 2, wherein the modifier is allyl chloride or allyl bromide in the first step.
6. The method for preparing a water-soluble naringin-based compound as claimed in claim 2, wherein the base in the first step is K2CO3,Na2CO3,BaCO3Or MgCO3。
7. The method of claim 2, wherein the phase transfer catalyst is at least one selected from the group consisting of benzyltriethylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium chloride, tetrabutylammonium hydrogen sulfate, trioctylmethylammonium chloride, dodecyltrimethylammonium chloride, and tetradecyltrimethylammonium chloride.
8. The method for preparing the water-soluble compound based on naringin according to claim 2, wherein in the second step, the molar ratio of the double bond modified naringin to the peroxide is 1: (1-3).
9. The method for preparing the water-soluble compound based on naringin according to claim 2, wherein the reaction temperature in the second step is 10-40 ℃ and the reaction time is 24-96 h.
10. The method for preparing the water-soluble compound based on naringin according to claim 2, wherein the peroxide in the second step is one or more of hydrogen peroxide, peracetic acid and m-chloroperoxybenzoic acid.
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