Method for preparing five ferulate single components by taking soapstock containing oryzanol as raw material

A technology of ferulic acid ester and oryzanol, applied in the field of plant extraction and separation, can solve the problems of high cost, difficult preparation and the like

Active Publication Date: 2020-04-14
HUNAN HUACHENG BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Prepared 5 kinds of monomers—24-methylene cycloartenyl ferulic acid ester, cycloartenyl ferulic acid ester, cycloartenyl ferulic acid ester, campesterol ferulic acid ester, β-

Method used

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  • Method for preparing five ferulate single components by taking soapstock containing oryzanol as raw material
  • Method for preparing five ferulate single components by taking soapstock containing oryzanol as raw material
  • Method for preparing five ferulate single components by taking soapstock containing oryzanol as raw material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] 1) Alkali alcohol hot melt and filter while hot. Put 100.3g of oryzanol-containing soapstock raw material into a 1000mL beaker, add 800mL of methanol, heat in a water bath at 52°C, and stir frequently until the temperature inside and outside the beaker is consistent. Then use 4% sodium hydroxide aqueous solution to adjust the pH of the system to 10.0, keep it warm at 52°C and keep stirring for 10 minutes, until the gluten soap base is dissolved and the insoluble matter is clearly separated, centrifuge while it is hot, and centrifuge at 3500 rpm for 5 minutes , collect the centrifugate to obtain the dissolved filtrate.

[0060] 2), acid precipitation and filtration. Adjust the pH of the dissolved filtrate to 7.0 with dilute hydrochloric acid with a concentration of 10%. After stirring for 5 minutes, let it stand still to precipitate a precipitate. Continue to stand still for 4 hours, filter with suction, and collect the precipitate to obtain 62.5 g of a yellow precipita...

Embodiment 2

[0078] 1) Alkali alcohol hot melt and filter while hot. Put 200.9g of oryzanol-containing soapstock raw material into a 2000mL beaker, add 1500mL of ethanol, heat in a water bath at 56°C, and stir frequently until the temperature inside and outside the beaker is consistent. Then use 5% potassium hydroxide aqueous solution to adjust the pH of the system to 9.5, keep it warm at 56°C and keep stirring for 12 minutes, until the gluten soap base is dissolved and the insoluble matter is separated obviously, suction filter while it is hot, and collect the filtrate to obtain the dissolved filtrate .

[0079] 2), acid precipitation and filtration. Adjust the pH of the dissolved filtrate to 6.8 with dilute sulfuric acid with a concentration of 5%. After stirring for 3 minutes, let it stand to precipitate the precipitate. Continue to stand for 5 hours, centrifuge at 3500 rpm for 5 minutes, and collect the precipitate to obtain 131.6 g of yellow precipitate.

[0080] 3), lipophilic orga...

Embodiment 3

[0098] Other operation is the same as embodiment 1, and difference is in step 4), cancels the development of the thin-layer chromatography of step 5. for the third time and the fourth time.

[0099] In step 4) of ⑦, the products of the high-purity group and the low-purity group were developed using thin-layer chromatography under three different conditions, methanol: isopropanol: n-hexane 1:2:2; acetone: ethyl acetate: petroleum ether 1 : 3: 4; Methanol: Ethyl Acetate: n-Hexane 1: 1: 1, spread distance 16cm, take it out to dry, and inspect with ultraviolet light, only 24-methylene cycloartenol ferulate and cycloarterol Pineapplenyl ferulic acid ester has a single spot under three different development conditions, and the other three ferulic acid ester products have multiple spots under a certain development condition, indicating that the purity of the obtained monomer has not reached 90%; The products of the low-purity group cannot all show a single spot under three different ...

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Abstract

The invention provides a method for preparing five ferulate single components by taking soapstock containing oryzanol as a raw material. The method comprises the following steps: 1) carrying out alkali-alcohol hot dissolution and filtering while the soapstock is hot; 2) carrying out acid precipitation and filtration; 3) degreasing and decoloring by using a lipophilic organic solvent; and (4) preparing thin-layer chromatography for separation; wherein the condition is that the content of the oryzanol in a precipitate crude product obtained after decoloring in the step (3) is 70-80wt%. The method is characterized in that soapstock with the oryzanol content of 10-20% is used as a raw material, a product with the oryzanol content of 70-80 wt% is obtained through a specific pretreatment purifying step, and then a monomer substance is separated and prepared through thin-layer chromatography; the purity of the five prepared monomers, namely 24-methylene cycloartanyl ferulate, cycloartenyl ferulate, cycloartanyl ferulate, campesterol ferulate and beta-sitosterol ferulate is greater than 90%; and the ferulate single components can be used as a reference substance for content determination,and can be used for external standard method content calculation and qualitative peak position calibration.

Description

technical field [0001] The invention belongs to the technical field of plant extraction and separation, and relates to a method for preparing five main ferulate monomers in oryzanol. Background technique [0002] Oryzanol exists in rice bran oil and is a mixture of ferulic acid esters mainly composed of triterpene (en) alcohols. Mainly homologues of cycloartenol (cycloartenol, cycloartenol, 2,4-methylenecycloartenol, cycloarpineol, etc.) and sterol homologues (sitosterol, stigmasterol Wait). The composition of various ferulic acid esters in the industrial product oryzanol is very complex, and their chemical structures and physical and chemical properties are very similar, so it is difficult to separate and purify by general chemical methods. [0003] Oryzanol is mainly composed of cycloartenol ferulate and sterol ferulate. [0004] 1. The content of cycloartenol ferulate in oryzanol is about 75% to 80%. Main composition and proportion: (1) 24-methylenecycloartenyl feruli...

Claims

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Application Information

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IPC IPC(8): C07J53/00C07J9/00G01N30/02G01N30/04G01N30/72
CPCC07J9/00C07J53/004G01N30/02G01N30/04G01N30/72G01N2030/047
Inventor 黄华学刘庚贵刘永胜
Owner HUNAN HUACHENG BIOTECH
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