Method for preparing secoisolariciresinol diglucoside and ferulic acid glucoside or ferulic acid glucoside ethyl ester

A technology of flax lignans and glucosides, which is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve the problems of no effective separation and large-scale production, and achieve low cost, The process is simple and easy, and the process is stable

Inactive Publication Date: 2009-09-23
SHANXI INST OF COAL CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Based on the above literature, most of the current research work is to obtain SDG and ferulic acid derivatives as a product, without effective separa...

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Weigh 200g of degummed dry linseed, add 400g of sodium hydroxide ethanol alkali solution with a pH value of 10, stir and extract in a 60°C water bath for 3 hours, filter, and repeatedly extract the filter residue with the above extract until the extract is colorless, and combine the filtrates . Adjust the filtrate to neutral with hydrochloric acid, concentrate the extract to a weight of 50 g, add 250 ml of water, and repeatedly extract with ethyl acetate until the ethyl acetate phase is colorless, separate the liquids, collect the water phase, and use X- 5 The macroporous resin completely adsorbs SDG and ethyl ferulic acid glucoside, and then adopts water and concentrations of 10v%, 20v%, 30v%, 40v%, 50v%, 60v%, 70v%, 80v%, respectively. 90v% ethanol solution was used as mobile phase for elution, 20v%, 30v% and 40v% ethanol eluents were collected, combined and evaporated to dryness to obtain flax lignans; 70v%, 80v%, 90v% ethanol eluents were collected, combined Evapor...

Embodiment 2

[0024] Weigh 400g of degummed dry linseed, add 1000g of potassium hydroxide ethanol alkali solution with a pH value of 11, stir and extract in a water bath at 40°C for 2.5 hours, filter, and repeatedly extract the filter residue with the above extract until the extract is colorless, and combine the filtrates . Adjust the filtrate to neutral with sulfuric acid, concentrate the extract to a weight of 60g, add 120ml of water, and repeatedly extract with methyl acetate until the methyl acetate phase is colorless, separate the liquids, collect the water phase, and use the collected water phase with AB- 8 The macroporous resin completely adsorbs SDG and ethyl ferulic acid glucoside, and then uses water and concentrations of 10v%, 20v%, 30v%, 40v%, 50v%, 60v%, 70v%, 80v%, respectively. 90v% ethanol solution was used as mobile phase for elution, 20v%, 30v% and 40v% ethanol eluents were collected, combined and evaporated to dryness to obtain flax lignans; 70v%, 80v%, 90v% ethanol eluen...

Embodiment 3

[0026] Weigh 200g of degummed dry linseed, add 1600g of ethanol solution of sodium hydroxide with a pH value of 12, stir and extract in a water bath at 50°C for 2 hours, filter, and repeatedly extract the filter residue with the above extract until the extract is colorless, and combine the filtrates. Adjust the filtrate to neutral with acetic acid, concentrate the extract to a weight of 70g, add 300ml of water, and repeatedly extract with toluene until the toluene phase is colorless, separate the liquids, collect the water phase, and use the collected water phase with AB-8 macroporous resin Completely adsorb SDG and ethyl ferulic acid glucoside, and then use water and ethanol with concentrations of 10v%, 20v%, 30v%, 40v%, 50v%, 60v%, 70v%, 80v%, and 90v% respectively The solution is used as the mobile phase to elute, collect 20v%, 30v% and 40v% ethanol eluents, combine and evaporate to dryness to obtain flax lignans; collect 70v%, 80v%, 90v% ethanol eluents, combine and evapora...

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Abstract

The invention relates to a method for preparing secoisolariciresinol diglucoside and ferulic acid glucoside or ferulic acid glucoside ethyl ester. The method comprises the following steps: after the impurity removal and the degumming are performed to the flax seeds, the flax seeds are mixed with alcoholic-alkaline solution, extracted for 2-5 h at the temperature of 40-60 DEG C and filtered, then the filter residue is extracted until the alcoholic-alkaline solution is achromatous, and then the merging is performed; the filtrate is added with acid to be adjusted to be neutral and concentrated until the weight is one sixth-one second of that of the original filtrate, then the water with volume 2-5 times of that of the concentrated solution is added in, the extraction is carried out through the organic solvent until the organic phase is achromatous and then the aqueous phase is collected; the secoisolariciresinol diglucoside and the ferulic acid glucoside ethyl ester in the aqueous phase are fully absorbed through macroporous resin, then the water and the alcohol solution are respectively taken as the mobile phases for elution, then the 20v percent, the 30v percent and the 40v percent of alcohol eluent are collected, merged and distilled to dryness to obtain secoisolariciresinol diglucoside; and the 70v percent, the 80v percent and the 90v percent of alcohol eluent are collected, merged and distilled to dryness to obtain ferulic acid glucoside ethyl ester. The invention has the advantages of entire simple and feasible process, stable process and low cost; and the secoisolariciresinol diglucoside and the ferulic acid glucoside ethyl ester or the ferulic acid glucoside can be obtained at the same time and the product reaches the higher purity.

Description

technical field [0001] The invention relates to a method for simultaneously preparing flax lignans and ferulic acid glucoside or ferulic acid glucoside ethyl ester by using flax seeds as raw materials. technical background [0002] Flaxseed (Flaxseed) is an important economic oil crop, rich in lignans, among which secoisolarix resinol diglucoside (SDG) has the highest content. In addition, flaxseed also contains other phenolic glycosides, such as coumaric acid glucoside and ferulic acid glucoside (see WO9630468A2). [0003] Secoisolaricoresinol diglucoside (SDG) is synthesized by bimolecular polymerization of phenylpropanoid, which is a compound with antioxidant and phytoestrogen activity, mainly derived from grains and other fiber-rich products, especially The content is as high as 1-3% in flaxseed. SDG has the effects of anti-tumor, lowering serum cholesterol, immune regulation, delaying aging, and protecting cardiovascular system, especially in inhibiting the growth of ...

Claims

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Application Information

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IPC IPC(8): C07H15/18C07H15/20C07H1/08A61P35/00A61P3/10A61P37/02A61P9/00A61P39/06A61P31/00
Inventor 侯相林葛晓静邓天昇
Owner SHANXI INST OF COAL CHEM CHINESE ACAD OF SCI
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