Method for preparing phloretin

A technology of phloretin and naringenin, which is applied in skin care preparations, preparation of organic compounds, food preparation, etc., can solve the problems of high cost, difficult content control, complicated process, etc., and achieve high product quality and low cost , the effect of simple operation

Active Publication Date: 2013-08-07
FOSHAN GOLDEN HEALTH TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the high price of phlorizin, the cost of these methods is high, and because the process is complicated and the process route is too long, there are many types of unknown impurities and the content is difficult to control, which is very unfavorable for the wide application of industrialization

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Dissolve 20 grams of naringin in 200 ml of 10% NaOH aqueous solution at room temperature, add 3 grams of commercial Raney nickel as a catalyst, vacuumize and replace with nitrogen, repeat 3 times and then introduce hydrogen, the pressure of hydrogen is 1 atmosphere. Then hydrogenate at room temperature for 20 hours. Filtration, the filtrate is adjusted to neutrality with 10% hydrochloric acid, and the solid is collected by filtration to obtain 26 grams of wet naringin dihydrochalcone, with a moisture content of 20% and a yield of 92%. 。 M.P.: 170~171℃;1H NMR (D2O-d6, 300 Hz 7.07 (d, J = 6, 2H), 6.75 (d, J = 6, 2H), 6.01 (s, 1H), 5.17 (d, J = 6.0, 1H ), 5.07 (s, 1H), 3.86 (d, J = 8.4, 1H), 3.34 (m, 10H), 3.22 (t, 2H), 2.87 (t, 2H),; ESI-MS m / z 581 [M-H]-.

Embodiment 2

[0026] 20 grams of naringin dihydrochalcone, 250 ml of 10% dilute hydrochloric acid, heated to reflux for 3 hours. Cool and collect the solid by filtration. The solid was recrystallized with 30% ethanol to obtain 8 grams of pure phloretin, with a yield of 90% and a content of 99.2%. M.P.: 257~258℃; 1H NMR (CD3Cl, 300 Hz): 6.97 (d, J = 6.0, 2H), 6.56 (d, J = 7.0, 2H), 5.84 (s, 2H), 3.21 (t, J = 6.0, 2H), 2.73 (d, J = 6.0, 2H), ESI-MS m / z 273 [M-H]-. Characteristic impurity A, content 0.3% M.P.: 170~171℃; 1H NMR (D2O-d6, 300 Hz 7.07 (d, J = 6, 2H), 6.75 (d, J = 6, 2H), 6.01 (s, 1H ), 5.17 (d, J = 6.0, 1H ), 5.07 (s, 1H), 3.86 (d, J = 8.4, 1H), 3.34 (m, 10H), 3.22 (t, 2H), 2.87 (t, 2H ),; ESI-MS m / z 581 [M-H]-. Characteristic impurity B, content 0.2%, ESI-MS m / z 434 [M-H]-.

Embodiment 3

[0028] Other conditions are the same as in Example 1, only the catalyst is replaced with 5% Pd / C. Yield 95%.

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PUM

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Abstract

The invention provides a method for preparing phloretin. The method comprises the following steps of: heating, hydrolyzing and purifying to obtain the phloretin under the action of dilute acid by using naringin dihydrochalcone. The naringin dihydrochalcone is prepared by the following method: performing catalytic hydrogenation on naringin under the medium pressure, normal temperature or heating action by using hydrogen in the presence of alkali liquor and rare metal catalyst, and collecting the naringin dihydrochalcone from the reaction system. The method is easy to operate, low in cost and high in product quality, and large-scale application of phloretin on the medicine, food and cosmetics can be well met.

Description

technical field [0001] The invention relates to a preparation method of phloretin. Background technique [0002] Phloretin is a dihydrochalcone compound, which is a natural active substance present in apples, pears and other fruits and various vegetables. estrogen-like activity. Dihydrochalcones have unique biological activities. Foreign researchers have long begun to study their role in health care, food additives and functional cosmetics, and have developed them by studying the relationship between compound structure and curative effect. The development of new drugs and the study of their mechanism of action and metabolic process in vivo are also in progress. [0003] Described in the patent of Setala Kai etc. that phloretin can activate cellular protein kinase, has curative effect to cell hyperplasia, is the antimutagenic factor in food, can be used for the treatment of skin cancer and other tumors (US4565806 Composition and method for rational treatment of cancer). Z...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/7048A23L1/30A61K8/60A61K8/35C07C49/83C07C45/65A61P35/00A61P3/10A61P25/16A61P17/14A61Q19/02A61Q19/08A61K31/7034A61K31/12
Inventor 周金林黄宝华卢宇靖
Owner FOSHAN GOLDEN HEALTH TECH CO LTD
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