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Method for catalytic hydrogenolysis of cinnamon proanthocyanidins high polymer to oligomer

A technology of proanthocyanidins and catalytic hydrogenolysis, applied in the direction of organic chemistry, etc., can solve the problems such as the degradation method of cinnamon high-polymer procyanidins, etc., and achieve the effect of improving the yield

Inactive Publication Date: 2008-08-13
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there has been no report on the degradation method of cinnamon high-polymeric proanthocyanidins

Method used

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  • Method for catalytic hydrogenolysis of cinnamon proanthocyanidins high polymer to oligomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Get 2.63g of cinnamon proanthocyanidin high polymer and dissolve it in 150ml volume percent concentration of 70% ethanol solution, put it into a reaction kettle, add 0.45g 10% palladium / carbon catalyst, and feed high-purity H 2 , under the condition of temperature of 100°C, pressure of 3.5MPa and stirring speed of 400rpm, the catalytic reaction was carried out for 200min. After the reaction is over, reduce the temperature of the reactor to room temperature, and slowly empty the H 2 , take out the reaction solution, filter, and recover the catalyst. The filtrate was concentrated under reduced pressure, ethanol was evaporated, and vacuum-dried to obtain 2.36 g of crude product with a yield of 89.7% and an average degree of polymerization of 2.82.

[0021] Dissolve the above crude product in water, put it on the LSA-21 macroporous resin column, wash it with 3 column volumes of distilled water, then elute with 3 column volumes of 50% ethanol solution, and concen...

Embodiment 2

[0022] Embodiment 2: Get 3.15 g of cinnamon proanthocyanidin high polymer and dissolve it in 150 ml volume percent concentration of 70% ethanol solution, put it into a reaction kettle, add 0.30 g of 10% palladium / carbon catalyst, and pass into high-purity H 2 , under the condition of temperature of 90°C, pressure of 3.0MPa and stirring speed of 400rpm, the catalytic reaction was carried out for 200min. After the reaction is over, reduce the temperature of the reactor to room temperature, and slowly empty the H 2 , take out the reaction solution, filter, and recover the catalyst. The filtrate was concentrated under reduced pressure, ethanol was evaporated, and vacuum-dried to obtain 2.75 g of product with a yield of 87.3% and an average degree of polymerization of 3.32.

[0023] Take the above dried crude product and dissolve it in water, put it on the LSA-21 macroporous resin column, wash it with 2 column volumes of distilled water, then elute with 3 column volumes of 60% eth...

Embodiment 3

[0024] Embodiment three: get cinnamon proanthocyanidin high polymer 4.50g and be dissolved in 150ml volume percentage concentration and be in the ethanol solution of 70%, pack in the reactor, add 0.60g 10% palladium / carbon catalyst, pass into high-purity H 2 , under the condition of temperature of 100°C, pressure of 3.5MPa and stirring speed of 400rpm, the catalytic reaction was carried out for 240min. After the reaction is over, reduce the temperature of the reactor to room temperature, and slowly empty the H 2 , take out the reaction solution, filter, and recover the catalyst. The filtrate was concentrated under reduced pressure, ethanol was evaporated, and vacuum-dried to obtain 4.17 g of crude product with a yield of 92.7% and an average degree of polymerization of 2.72.

[0025] Take the above dry crude product and dissolve it in water, put it on the LSA-21 macroporous resin column, wash it with 3 column volumes of distilled water, then elute with 4 column volumes of 70%...

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Abstract

The invention relates to a method for catalyzing and hydrogenolysis of cinnamon procyanidine high polymers to procyanidine low polymers. The method comprises: extracting cinnamon procyanidine high polymers; hydrogenation catalyzing and degradating cinnamon procyanidine high polymers to obtain crude products; separating crude products LSA-21 macroporous resin column to obtain procyanidine low polymers. The invention uses Pd / C catalyst and hydrogen to catalyze and hydrogenize cinnamon high poly-procyanidine to procyanidine low polymers, solves activity problems of the products, and maintains the bioactivity of procyanidine. The method of the invention can not only open C4-C8 keys, but also open C2-O-C7 keys, thereby realizing depolymerization of high polymers. In the reaction, reagents such as acid or alkali, which have pollution on environment, are avoided to be use, ethanol aqueous sollution can be recycled. The low poly-procyanidine obtained by catalyzing and hydrogenolysis, improves the rate of low poly-procyanidine in cinnamon, widens the application range in food and cosmetic fields.

Description

technical field [0001] The invention relates to a method for degrading cinnamon proanthocyanidin high polymers into proanthocyanidin oligomers. In particular, a method for degrading cinnamon proanthocyanidin high polymers into proanthocyanidin oligomers by catalytic hydrogenolysis. 2. Technical background [0002] Proanthocyanidins are a class of polyphenolic substances condensed from flavan-3-ols. They are secondary products of plant metabolism and widely exist in the flowers, leaves and bark of most plants. Oligomeric proanthocyanidins have significant physiological functions in anti-cancer, anti-oxidation, anti-mutation, hypoglycemic, anti-inflammation, pain relief, hemostasis, prevention of arteriosclerosis and skin allergies, etc., which are beneficial to human health. Studies have shown that the biological activity of proanthocyanidins is related to the composition of monomers, the form of linkages between monomers and the degree of polymerization. Its biological act...

Claims

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Application Information

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IPC IPC(8): C07D311/62C07D493/08
Inventor 雍克岚吕敬慈李长运陈旭魏莎莎马颖清
Owner SHANGHAI UNIV
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