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Method for removing isonaringin from natural product hesperidin

A technology for isonaringin and hesperidin, which is applied in the field of purification of natural extraction product hesperidin, can solve the problems of difficulty in finding and dissolving hesperidin, impurity removal, solvent residue and the like

Active Publication Date: 2020-11-24
崔仁发
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Theoretically speaking, the impurity isonaringin can be separated by recrystallization, but the difficulty is that it is difficult to find a suitable solvent to dissolve hesperidin
At present, the solvents that can dissolve hesperidin, such as pyridine, N,N-dimethylformamide (DMF), morpholine, dimethyl sulfoxide (DMSO), etc., are all high-boiling solvents, which are not easy to separate from the product after recrystallization , causing solvent residue, which is disastrous for the natural product hesperidin as a food or drug
However, if it is dissolved in an alkaline water solvent such as NaOH water solvent and then acidified, the impurities and the main component of hesperidin will be precipitated together due to the similar pKa, and the purpose of removing impurities cannot be achieved.

Method used

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  • Method for removing isonaringin from natural product hesperidin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment example 1

[0026] Take a 500mL three-neck flask, respectively install a syringe with a needle (put it into the rubber stopper first), an electric stirrer, and a thermometer, and place it in a fume hood. Measure 150mL of pure water and add it to a three-necked flask. Add 3.0 g of solid NaOH and stir to dissolve. Then slowly add 20.0g hesperidin 1, stir, and dissolve completely. Put a lot of solid ice cubes directly into the three-necked flask, and the temperature dropped to 8°C. Slowly push 0.3mL of dimethyl sulfate into the syringe, and the dropwise addition is completed within 5 minutes. The temperature of the solution in the flask is between 8-10°C, and the volume is about 300mL. After the dropwise addition was completed overnight, the temperature of the solution was slowly returned to normal temperature, and the reaction was stirred for 10 hours.

[0027] The next morning, add 9.5 g of activated carbon and stir at 30°C for 2 hours to decolorize. Filter and clean the activated char...

Embodiment example 2

[0029] Pour 150 mL of pure water into the three-necked flask, add 3.5 g of solid NaOH, 20.0 g of hesperidin 1, and stir until completely dissolved. Ice cubes were put into the flask to cool down to 0°C, and 0.2 mL of dimethyl sulfate was slowly added dropwise, and the addition was completed within 3 minutes. After the dropwise addition was completed, wait for the solution to return to normal temperature slowly, and heat to 30° C. to react for 4 hours.

[0030] It was acidified to neutral with dilute hydrochloric acid, and a large amount of yellow precipitates precipitated out of the solution immediately. Let stand for 2 hours, and filter with suction. Dry at 60° to get 18.6g hesperidin. The isonaringin was reduced from 2.8% to 0.8%, and the yield was 93.0%.

Embodiment example 3

[0032] Pour 150mL of pure water and 4.0g of solid NaOH into the three-necked flask, and slowly add 20.0g of hesperidin 1 after dissolution, and stir until completely dissolved. Cool down to -8°C with ice cubes, slowly push in 0.4 mL of dimethyl sulfate with a syringe, and complete the addition within 7 minutes. The temperature in the flask rises slowly to about 0°C, and the volume of the solution is 350 mL. After the temperature of the solution returned to normal temperature slowly, the reaction was heated at 40°C for 3 hours. At the same time, weigh 200g of resin AB-8 and pack it into a column, and treat it with ethanol, dilute hydrochloric acid, and dilute NaOH respectively for use.

[0033] After the reaction is completed, the solution is passed through the pretreated AB-8 macroporous adsorption column. The passing solution was acidified to neutral with dilute hydrochloric acid, and a large amount of precipitates appeared in the solution immediately, which was allowed to sta...

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Abstract

The invention provides a method for removing an impurity isonaringin from a plant extract hesperidin. According to the method, a 4'-phenolic hydroxyl group of the isonaringin is subjected to a selective reaction by using a small amount of phenolic hydroxyl protecting groups so as to weaken polarity of the isonaringin, and then, adsorption is carried out through nonpolar or low-polarity macroporousresin so as to remove the isonaringin; and during the selective reaction of the 4'-phenolic hydroxyl group of the isonaringin, a 3'-phenolic hydroxyl group of the hesperidin also will participate inthe reaction, the polarity of obtained products is also weakened, and the obtained products will also be adsorbed and removed by the macroporous resin like the isonaringin. According to the method, through difference of reactivity of active phenolic hydroxyl groups of the isonaringin and the hesperidin, impurity removal is carried out by using chemical reactions and resin adsorption, a product with the isonaringin content of 0% and the hesperidin purity of 98% or more can be obtained through sacrificing a small amount of major components, and thus, the requirements on production of high-purityraw materials of diosmin are met.

Description

technical field [0001] The invention belongs to the technical field of plant extraction, and in particular relates to a purification method of a natural extraction product hesperidin. Background technique [0002] Hesperidin, also known as nobiletin, dihydroflavone glycoside. It is an active flavonoid extracted from the fruit or peel of citrus plants of Rutaceae, such as Citrus aurantium, orange peel, orange peel, etc. The pure product is pure white fine branch-like needle-like crystals. It has the functions of reducing the fragility of capillaries, protecting capillaries, preventing capillary rupture and bleeding (similar to vitamin P), inhibiting the increase of blood cholesterol and preventing arteriosclerosis. It is a drug for treating hypertension and myocardial infarction; Oxidation, blood sugar lowering, anti-inflammatory and analgesic, anti-tumor, anti-viral effects. In addition to being a drug, food and cosmetic additive, hesperidin is mainly used as a raw materia...

Claims

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Application Information

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IPC IPC(8): C07H17/07C07H1/06
CPCC07H17/07C07H1/06Y02P20/55
Inventor 崔仁发
Owner 崔仁发
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