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6-O-acyl raffinose monoester and synthesis method thereof

A technology of acyl raffinose monoester and acyl raffinose, which is applied in the field of 6-O-acyl raffinose monoester and its synthesis, and can solve the practical application of raffinose monoester synthesis route. Research and other issues to achieve the effect of shortening time-consuming, optimizing process conditions and convenient operation

Inactive Publication Date: 2019-09-24
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although raffinose has a potential that cannot be ignored, only a small amount of raffinose fatty acid ester derivatives have been successfully prepared, and most of the work is still in theoretical research, and most studies focus on the region of the fatty acid chain during the esterification process selectivity, while little research has been done on the synthetic pathways of raffinose monoesters and their practical applications in the food industry

Method used

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  • 6-O-acyl raffinose monoester and synthesis method thereof
  • 6-O-acyl raffinose monoester and synthesis method thereof
  • 6-O-acyl raffinose monoester and synthesis method thereof

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Experimental program
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Effect test

Embodiment 1

[0035] 6-O-hexanoyl raffinose monoester (RH) synthesis method such as figure 2 That is, the synthesis method of 6-O-acyl raffinose monoester of the present invention is shown in the flow chart. The synthesis method selects vinyl caproate as the reactant, and is separated by enzymatic reaction and fast chromatography to change the molecular weight and structure of the sugar ester. , Specifically including the following steps and process conditions:

[0036] Step 1: Enzymatic reaction

[0037] (1) After adding 45 mL of pyridine, 55 mL of tert-butanol (9:11, v / v) and magnets in turn, treat the mixture obtained with 1 g of lipase TLIM and 4 mmol of D-raffinose, and magnetically stir at 50°C for 5 minutes , Treat the mixture with vinyl caproate, the molar mass ratio of the raffinose to vinyl caproate is 1:5, that is, add 20 mmol of vinyl caproate;

[0038] (2) The resulting mixture was magnetically stirred at 50°C for 14 hours, until all D-raffinose had been consumed by TLC analysis, co...

Embodiment 2

[0047] The synthesis method of 6-O-myristoyl raffinose ester (RM) is as figure 2 That is to say, as shown in the flow chart of the 6-O-acyl raffinose monoester synthesis method of the present invention, the synthesis method selects vinyl myristate as the reactant, and undergoes enzymatic reaction and fast chromatographic elution separation to change the molecular weight of the sugar ester And structure, specifically including the following steps and process conditions:

[0048] Step 1: Enzymatic reaction

[0049] (1) After adding 45 mL of pyridine, 55 mL of tert-butanol (9:11, v / v) and magnets in sequence, treat the mixture obtained with 1 g of lipase TLIM and 4 mmol of D-raffinose, and magnetically stir at 55°C for 8 minutes The molar mass ratio of the raffinose to vinyl myristate is 1:6, that is, 24 mmol of vinyl myristate is added, and the resulting mixture is magnetically stirred at 55°C for 14 hours, until all D is determined by TLC analysis. -Raffinose has been consumed, co...

Embodiment 3

[0057] 6-O-palmitoyl raffinose monoester (RP) synthesis method such as figure 2 That is, as shown in the flow chart of the 6-O-acyl raffinose monoester synthesis method of the present invention, the synthesis method selects vinyl palmitate as the reactant, and undergoes enzymatic reaction and fast chromatographic elution separation to change the molecular weight and structure of the sugar ester. Specifically include the following steps and process conditions:

[0058] Step 1: Enzymatic reaction

[0059] After adding 45 mL of pyridine, 55 mL of tert-butanol (9:11, v / v) and magnets in sequence, the mixture obtained by treating with 1 g of lipase TLIM and 4 mmol of D-raffinose was magnetically stirred at 55° C. for 5 minutes. The molar mass ratio of raffinose to vinyl palmitate is 1:5, that is, 20 mmol of vinyl palmitate is added, and the resulting mixture is magnetically stirred at 55°C for 14 hours, until all D-raffinose has been determined by TLC analysis. After being consumed, c...

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Abstract

The invention provides a 6-O-acyl raffinose monoester and a synthesis method thereof. On the basis of designing a novel structural model of a raffinose monoester, four kinds of 6-O-acyl raffinose monoesters with different carbon chain lengths are successfully synthesized for the first time. In the synthesis method, reactants with fatty chains of different lengths are selected, through enzymatic reaction, the structure of a glycosyl ester can be accurately formed a reaction site can be controlled, and the molecular weight and structure of the glycosyl ester are changed by continuously forming new fatty chains; and then, the 6-O-acyl raffinose monoester with the required molecular weight and structure is obtained by rapid chromatography elution separation. According to the 6-O-acyl raffinose monoester and the synthesis method thereof, products of different properties are obtained to meet different product requirements, and the synthesis method has simple steps, convenient to operate, significantly shortened in time consumption and environment-friendly; the produced raffinose glycosyl ester has good performance and can be used as an excellent foaming agent and emulsifier; and the monoester output is high and the cost is low, and the 6-O-acyl raffinose monoester is suitable for large-scale industrial production.

Description

Technical field [0001] The invention belongs to the research field of food additives, and specifically relates to 6-O-acyl raffinose monoester and a synthesis method thereof. Background technique [0002] With the increasing living standards of today's society, people are no longer satisfied with ordinary foods that provide nutrients to the human body, but have a higher pursuit of foods that can promote health. This trend has stimulated the research and development of new food additives by scientific researchers, especially those food additives with additional health benefits have become a hot spot in the food industry. In this regard, short-chain carbohydrates (also known as "prebiotics") are favored for their unique properties. In addition to being non-cariogenic and low in calories, they can effectively stimulate the growth of beneficial bacteria in the colon. Therefore, the production of certain non-digestible oligosaccharides into their corresponding fatty acid esters can m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P19/00C12P7/64C07H13/06A23L29/10
CPCA23L29/10A23V2002/00C07H13/06C12P7/6436C12P19/00A23V2200/222
Inventor 蓝平海耀文李璇
Owner JINAN UNIVERSITY
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