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New aurantiamarin synthesizing technique

A new hesperidin and synthetic process technology, applied in the direction of organic compound/hydride/coordination complex catalyst, preparation of sugar derivatives, sugar derivatives, etc., can solve complex operation, loss of industrial production, and long production cycle and other problems, to achieve the effect of simple synthesis conditions, low production cost, and fast reaction speed

Active Publication Date: 2010-10-20
成都华康生物工程有限公司
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Problems solved by technology

In patent No. US3375242, US3522236, foreign patents of ES545276 and articles titled "Synthesis of various fiavanone7-neohesperidosides." (Sciences Chimiques (1966), 262 (24), 1712-14.) and "Dihydrochalcone sweeteners: preparation of neohesperidin dihydrochalcone." (Industrial & Engineering Chemistry Product Research and Development (1974), 13(2), 125-9.) In the literature, either naringin is directly mixed with a large excess of isovanillin (12 times in excess) After reaction in alkaline aqueous solution or alcohol solution, acidify to obtain neohesperidin, or hydrolyze naringin in alkaline aqueous solution to obtain root bark acetophenone-4'-β-neohesperidin, and then mix with a large excess Neohesperidin is obtained by acidifying isovanillin after reaction in alkaline aqueous solution or alcohol solution. These methods all have the problems of low yield, large amount of raw material isovanillin, and high cost, because the possibility of industrial production has been lost. sex
Patent No. is in the foreign patent of US3947405, by using tetrahydropyrrole and acetic acid as catalyzer, with root bark acetophenone-4'-B-neohesperidoside and isovanillin in dehydrated alcohol by the molar ratio of 1:1 Neohesperidin can be synthesized by reacting under the protection of argon for 12 hours, which is the most suitable production process for industrialization in the past, but it still has the following disadvantages: 1. It needs protection of argon; 2. It needs to use absolute ethanol, recovered Anhydrous ethanol needs to be dried before it can be recycled; 3. It is necessary to use liquid tetrahydropyrrole, which is more expensive and has a strong odor, as a catalyst; 4. The reaction time is longer; 5. The yield is not too high
Because of the existence of these shortcomings, this process has problems such as strict process, complex operation, long production cycle, and high cost. Therefore, it is necessary to find a new way to synthesize neohesperidin

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0018] The operating method of this example synthetic neohesperidin is carried out according to the following two steps:

[0019] Synthesis of root bark acetophenone-4′-β-neohesperidoside: Dissolve 6.0g of sodium hydroxide in 50mL of tap water with stirring, then slowly add 4.5g of naringin into the alkaline solution with stirring , after stirring completely to dissolve, start to heat up to reflux at 100°C, count from the start of reflux, stop heating after reflux and stirring for 1.5 hours, cool to below 30°C, slowly add concentrated hydrochloric acid to neutralize to a pH value of about 6.5, and a yellow solid precipitates. Heat again to above 70°C to dissolve all the solids, stop heating, cool naturally, let stand for 2 hours, then filter through the Buchner funnel, vacuum dry at 60°C to obtain 2.5g of yellow root bark acetophenone-4'- β-Neohesperidoside, yield 68%.

[0020] Synthesis of neohesperidin: Add 2.0g root bark acetophenone-4'-β-neohesperidoside into 12mL85% etha...

Embodiment 2

[0022] The operating method of this example synthetic neohesperidin is carried out according to the following two steps:

[0023] Synthesis of root bark acetophenone-4′-β-neohesperidoside: 3.5kg of sodium hydroxide was dissolved in 30L of tap water under stirring, and then 2.8kg of naringin was slowly added to the alkaline solution under stirring , after stirring to dissolve completely, start heating and heating to 100°C to reflux, count from the start of reflux, reflux at 100°C and stir for 2 hours, then stop heating, cool to below 30°C, slowly add concentrated hydrochloric acid to neutralize to a pH value of about 6.5, and yellow precipitates solid. Heating again to above 70°C to dissolve all the solids, then stop heating, cool naturally, let stand for 2 hours, then filter through Buchner funnel, vacuum dry at 60°C to obtain 1.6kg of yellow root bark acetophenone-4'- β-Neohesperidoside, the yield is 70%.

[0024] Synthesis of neohesperidin: Add 1.5kg root bark acetophenone...

Embodiment 3

[0026] The operating method of this example synthetic neohesperidin is carried out according to the following two steps:

[0027] Synthesis of root bark acetophenone-4'-β-neohesperidoside: 200kg of sodium hydroxide was dissolved in 1700L tap water under stirring, then 150kg of naringin was slowly added to the alkaline solution under stirring, and stirred After completely dissolving, start heating to reflux at 100°C, count from the beginning of reflux, reflux at 100°C and stir for 2 hours, then stop heating, cool to below 30°C, slowly add concentrated hydrochloric acid to neutralize to a pH value of about 6.5, and a yellow solid precipitates. Heat again to above 70°C to dissolve all the solids, stop heating, cool naturally, let stand for 2 hours, then centrifuge and filter, and vacuum dry at 60°C to obtain 85.5kg of yellow root bark acetophenone-4'-β- Neohesperidoside, yield 69%.

[0028] Synthesis of neohesperidin: Add 85kg root bark acetophenone-4'-β-neohesperidoside into 620L...

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Abstract

A new aurantiamarin synthesizing technique relates to a method for synthesizing new aurantiamarin by using naturally abstracted naringin as raw materials. The traditional aurantiamarin synthesizing technique has the problems of low efficiency and high cost or the problems of hard condition, complex operation and long production period. The synthesizing method of the invention using naringin as raw materials comprises the steps of: a. synthesizing acetophenone-4'-beta-new flavedo glucoside and b. synthesizing new aurantiamarin. The synthesizing technique of the invention needs no hard condition, has simple operation, short period, and stable and easily controlled synthesizing condition, and is easy to separate and purify. The product yield of new aurantiamarin is equal to or more than 95% and the purity is equal to or more than 96% by using proline as an efficient catalyst for synthesizing new aurantiamarin, the production cost is low, the environmental pollution is small and the technique is suitable for industrializing production of the new aurantiamarin.

Description

technical field [0001] The invention belongs to the synthesis process of plant raw materials, and mainly relates to a method for synthesizing another more important plant raw material with a plant raw material as a basic raw material, in particular to a method for synthesizing neohesperidin with naringin as a basic raw material synthesis process. Background technique [0002] Neohesperidin belongs to dihydroflavonoids in flavonoids. It was first discovered in plants, usually distributed in limes, citrus aurantium, citrus aurantium, and immature pomelo. The molecular formula of neohesperidin is C 28 h 34 o 15 , the molecular weight is 610.56, and its structural formula is: [0003] [0004] Pharmacological studies have shown that flavonoids such as neohesperidin in Citrus aurantium and Citrus aurantium have inhibitory effects on the non-physiological contraction of smooth muscle in rats, and can resist the spasmodic contraction caused by barium chloride and acetylcholi...

Claims

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Application Information

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IPC IPC(8): C07H17/07C07H1/00B01J31/04
Inventor 夏时川陈宁吴尚全黄清东
Owner 成都华康生物工程有限公司
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