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Glycoamine Amadori derivative as well as preparation method and application thereof

A technology of derivatives and sugar amines, applied in the field of sugar amine Amadori derivatives and their preparation, can solve the problems of high price of Amadori compounds, lack of means for regulating their degradation products, complex types of thermal degradation products and the like

Active Publication Date: 2021-06-08
HENAN AGRICULTURAL UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the current research on Amadori compounds still has the following problems: First, the synthesis and purification process of Amadori compounds is cumbersome, requiring multiple column chromatography, and the yield is low, resulting in high prices for pure Amadori compounds
Second, there are complex types of thermal degradation products of Amadori compounds, which produce both beneficial aroma substances and harmful substances. At present, there is a lack of means to regulate their degradation products.

Method used

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  • Glycoamine Amadori derivative as well as preparation method and application thereof
  • Glycoamine Amadori derivative as well as preparation method and application thereof
  • Glycoamine Amadori derivative as well as preparation method and application thereof

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preparation example Construction

[0026] The present invention provides a method for preparing the sugar amine Amadori derivative described in the above technical scheme, comprising the following steps:

[0027] (1) fructose, acetone and vitriol oil are mixed, carry out condensation reaction, obtain protected fructose;

[0028] (2) Mix the protected fructose obtained in the step (1) with trifluoromethanesulfonic anhydride, 2,6-di-tert-butyl-4-picoline and anhydrous dichloromethane, and carry out a substitution reaction to obtain intermediate body;

[0029] (3) mixing the intermediate obtained in the step (2) with amino acid ester, N,N-diisopropylethylamine and anhydrous dimethylformamide, and performing a substitution reaction to obtain sugar amine Amadori derivatives; The amino acid esters include proline esters, alanine esters or tryptophan esters.

[0030] The invention mixes fructose, acetone and concentrated sulfuric acid for condensation reaction to obtain protected fructose. In the present invention,...

Embodiment 1

[0084] (1) Mix 11.1mmol fructose, 39mL acetone and 36.4mmol concentrated sulfuric acid (the ratio of the amount of fructose, acetone and concentrated sulfuric acid is 1:47.7:3.28), stir in an ice-water bath for 4h to carry out condensation reaction, to the condensation reaction Add 27.8 mL of ice NaOH solution with a concentration of 5.5 mol / L to the final system, extract 8 times with 30 mL of anhydrous dichloromethane, dry the extract over anhydrous magnesium sulfate, filter and concentrate under reduced pressure to obtain protected fructose;

[0085] (2) Under nitrogen protection, 2.3mmol protected fructose, 2.3mmol trifluoromethanesulfonic anhydride and 1.5mmol 2,6-di-tert-butyl-4-picoline were added to 10mL of anhydrous dichloromethane (protected The ratio of the amount of fructose to trifluoromethanesulfonic anhydride, 2,6-di-tert-butyl-4-picoline and anhydrous dichloromethane is 1:1:0.65:67.8), reacted in ice-water bath for 1h , carry out the substitution reaction, after...

Embodiment 2

[0090] The difference from Example 1 is that the proline ester is replaced by alanine ester, and the remaining steps are the same as in Example 1, and the yield is 80%.

[0091] The sugar amine Amadori derivatives prepared in this example have the structure shown in formula (II).

[0092] The H NMR spectrum of the sugar amine Amadori derivatives prepared in this embodiment is: H NMR spectrum: 1 H NMR (400MHz, CDCl 3 , containing 0.03% TMS, 25°C): δ: 4.58 (dd, J = 7.9Hz, J = 2.6Hz, 1H, CH), 4.34 (d, J = 2.5Hz, 1H, CH), 4.22 (dd, J =7.9Hz,J=1.0Hz,1H,CH),4.16(q,J=6.8Hz,2H,CH 2 ),3.81(dd, 2 J=60.2Hz, 3 J=13.0Hz, 2H, CH 2 ), 3.49(q, J=7.0Hz, 1H, CH), 2.85(m, 2H, CH 2 ),1.53(s,3H,CH 3 ),1.47(s,3H,CH 3 ),1.43(s,3H,CH 3 ),1.34(s,3H,CH 3 ),1.29-1.25(m,6H,2CH 3 ).

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Abstract

The invention relates to the technical field of Amadori derivatives, provides a glycosamine Amadori derivative, and specifically defines the structural formula of the glycosamine Amadori derivative, and the structural formula of the glycosamine Amadori derivative comprises the glycosamine Amadori derivative with three structures obtained by reaction of three different amino-acid esters and fructose. The glycosamine Amadori derivative with the three structures can be subjected to pyrolysis under the heating condition, multiple products are obtained through pyrolysis, and the pyrolysis products are stable in chemical property, lasting in effect and high in aroma quality and can be used for improving the quality of cigarettes. Experimental results show that the glycosamine Amadori derivative provided by the invention can be pyrolyzed into various products with fragrance, and can bring more harmonious mouth feel during cigarette panel test, so that the smoking quality is improved.

Description

technical field [0001] The invention relates to the technical field of Amadori derivatives, in particular to a sugar amine Amadori derivative and its preparation method and application. Background technique [0002] Maillard reaction (Maillard reaction), also known as carbonyl ammonia reaction, refers to the complex reaction between carbonyl compounds (reducing sugars) and amino compounds (amino acids, proteins and peptides) in food. Amadori compounds are Maillard The key intermediate product in the German reaction. Amadori compounds can be degraded to produce a variety of aroma substances such as aldehyde esters, furans, pyrazines, and pyrroles, which play an important role in the color, flavor, and quality of substances. Studies have shown that Amadori compounds can be used as a class of flavor precursors and play an important role in the color, flavor and nutritional value of food. [0003] However, the current research on Amadori compounds still has the following probl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/12C07H19/044C07H1/00A24B3/12A24B15/40
CPCC07H19/044C07H15/12C07H1/00A24B15/406A24B3/12
Inventor 李瑞望运滔阴晓晴张士怡赵铭钦
Owner HENAN AGRICULTURAL UNIVERSITY
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