Synthesis method of Robtein

A synthesis method and alkaline technology, applied in the field of Robtein synthesis, can solve the problems of difficult purification, high production cost, single source, etc., and achieve the effects of time-saving and labor-saving synthesis process, short reaction time and low production cost.

Active Publication Date: 2019-04-19
SHAANXI SCI TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the current market supply of Robtein is very small, and commercial Robtein is mainly used as a standard product for content determination, qualitative and quantitative analysis, and pharmacological experimental research of related products. The reason is that Robtein has a single source, mainly extracted from plants. However, there are not many types of plants containing Robtein, and the content is low, and the resources are limited; and to extract high-purity Robtein from plants with low content, it is necessary to overcome many problems such as solvent recovery, decolorization and degreasing, residue treatment, separation and enrichment, etc. and difficult, the purification is very difficult, the yield is very low, and the production cost is very high

Method used

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  • Synthesis method of Robtein
  • Synthesis method of Robtein

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] (1) Preparation of basic catalyst

[0031] Weigh 30 parts of sodium hydroxide by weight, dissolve it in distilled water, then weigh 70 parts of aluminum oxide, add aluminum oxide to the above sodium hydroxide solution, stir evenly, evaporate the water under reduced pressure to dryness, and put the The obtained powder was dried in a drying oven at 105 °C for 3 hours, then placed in a muffle furnace for calcination at 600 °C for 5 hours, taken out from the muffle furnace and cooled in a desiccator to obtain a sodium hydroxide / alumina basic catalyst ,spare.

[0032] (2) Synthesis of Robtein

[0033] Weigh 3.5kg of syringaldehyde, dissolve with 88.5L of absolute ethanol, for subsequent use;

[0034] Weigh 3.2 kg of paeonol, dissolve it in 123 L of dehydrated alcohol in the reaction kettle; add 1.11 kg of standby alkaline catalyst at room temperature of 5 ° C, stir evenly, under continuous stirring, slowly add standby cloves in 35min Aldehyde ethanol solution; the reactio...

Embodiment 2

[0036] (1) Preparation of basic catalyst

[0037] Same as Example 1;

[0038] (2) Synthesis of Robtein

[0039] Weigh 6.5kg of syringaldehyde, dissolve it with 150L of absolute ethanol, for subsequent use;

[0040] Weigh 5.93kg of paeonol, dissolve with 200L of dehydrated alcohol in the reaction kettle; add 1.8kg of standby alkaline catalyst at room temperature of 18°C, stir evenly, under continuous stirring, slowly add standby cloves in 33min Aldehyde ethanol solution; the reaction solution gradually turned into a brownish-yellow turbid solution, and after continuing to stir for 13h, the reaction solution became turbid and brown, and the degree of reaction was detected by TLC method, and then stirred for 3h to ensure a sufficient reaction; after the reaction was completed, Add absolute ethanol to dissolve the organic matter as much as possible, quickly suction filtration to remove the basic catalyst; distill the suction filtrate under reduced pressure to recover ethanol, an...

Embodiment 3

[0042] (1) Preparation of basic catalyst

[0043] Same as Example 1;

[0044] (2) Synthesis of Robtein

[0045] Weigh 9.1kg of syringaldehyde, dissolve with 180L of absolute ethanol, for subsequent use;

[0046]Weigh 8.3 kg of paeonol, dissolve it in 260 L of absolute ethanol in the reaction kettle; add 2.3 kg of standby alkaline catalyst at room temperature of 26 ° C, stir evenly, under continuous stirring, slowly add standby cloves in 30 min Aldehyde ethanol solution; the reaction solution gradually turned into a brownish-yellow turbid solution, and after continuing to stir for 13h, the reaction solution became turbid and tan, the degree of reaction progress was detected by TLC method, and then stirred for 2h to ensure a sufficient reaction; after the reaction was completed, Add anhydrous ethanol to dissolve the organic matter as much as possible, quickly suction filtration to remove the basic catalyst; distill the suction filtrate under reduced pressure to recover ethanol...

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Abstract

The invention discloses a synthesis method of Robtein. The method comprises the steps that syringaldehyde and paeonol serve as raw materials, under the action of a basic catalyst, by means of a Claisen-Schmidt condensation reaction, 2',4-dihydroxy-3,4',5-trimethoxy chalcone is directly synthesized, and under the action of hydrobromic acid, ether linkages in molecules are broken and transformed into 2',3,4,4',5-pentahydroxy chalcone which is Robtein, recrystallization is conducted, and then Robtein high in purity can be obtained. The feeding ratio of syringaldehyde to paeonol is syringaldehyde(mol):paeonol(mol)=1:1. Accordingly, synthesis of Robtein is carried out at room temperature and atmospheric pressure, fewer steps are adopted, the reaction time is short, and continuous synthesis canbe conducted without complex separation, and the method is suitable for industrialized production; the total yield exceeds 78%, and the purity of the product is 95% or above. The synthetic process isenvironmental friendly.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a Robtein synthesis method. Background technique [0002] The chemical name of Robtein is (E)-1-(2,4-dihydroxyphenyl)-3-(3,4,5-trihydroxyphenyl)-2-propen-1-one, also known as 2' ,3,4,4',5-Pentahydroxychalcone is a natural chalcone compound that exists in a very small amount in medicinal plants such as Acacia, Robinia pseudoacacia, and Wangjiangnan. Its molecular structure is: [0003] [0004] Studies have found that chalcone compounds have significant biological activities, such as anti-tumor, anti-inflammatory, anti-fungal, anti-viral, and diabetes treatment. Studies suggest that chalcone compounds can inhibit tumor cell proliferation by inducing tumor cell apoptosis and blocking tumor cell division, while increasing the expression of p53 protein, cyclin A, B and cyclin-dependent kinase 1 (CDK1) The expression of the molecule is reduced. Some studies also believe ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/64C07C49/835C07C45/74C07C49/84
CPCC07C45/64C07C45/74C07C49/835C07C49/84
Inventor 田光辉刘存芳史娟刘全庞海霞孙志锋刘军海
Owner SHAANXI SCI TECH UNIV
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