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Preparation method of S-2-(4-methoxyphenoxy) sodium propionate

A technology of methoxyphenoxy and p-methoxyphenol, which is applied in the field of preparation of sweetness inhibitors, can solve problems such as food sweetness, and achieve the effects of eliminating potential hazards, good sweetness suppression effect, and reducing metabolic burden

Inactive Publication Date: 2015-06-24
HUAZHONG AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But when sugar is added in a large amount in food, it will cause the food to be too sweet and too greasy

Method used

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  • Preparation method of S-2-(4-methoxyphenoxy) sodium propionate
  • Preparation method of S-2-(4-methoxyphenoxy) sodium propionate
  • Preparation method of S-2-(4-methoxyphenoxy) sodium propionate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] 1) Add 13.70 g (0.072 mol) of p-toluenesulfonyl chloride, 7.80 g (0.075 mol) of methyl D-lactate, and 30 mL of toluene into a 150 mL two-necked flask, add 11.4 g of triethylamine dropwise, and react for 12 hours to complete the reaction. Filter, wash with water (30mL×2), dry the organic phase with anhydrous sodium sulfate, evaporate the solvent to obtain methyl R-2-(4-methylbenzenesulfonate)propionate.

[0028] 2) Add 30g of dichloromethane, 4.380g (0.03mol) of sodium p-methoxyphenate, 0.32g (0.001mol) of tetra-n-butylammonium bromide into a 250mL two-necked flask, and then dropwise add the resulting R- 7.74 g (0.03 mol) of methyl 2-(4-methylbenzenesulfonate) propionate and 20 g of dichloromethane mixed solution were heated and refluxed for 20 hours.

[0029] 3) Then add 1.5g of sodium hydroxide and 15mL of water to the solution, reflux for hydrolysis, point the plate to follow the reaction, after the hydrolysis is complete, separate the liquid to collect the water phas...

Embodiment 2

[0031] 1) Add 12.72 g (0.072 mol) of benzenesulfonyl chloride, 8.85 g (0.075 mol) of D-ethyl lactate, and 30 mL of toluene into a 150 mL two-necked flask, add 11.4 g of triethylamine dropwise, and react for 12 hours to complete the reaction. Filter, wash with water (30mL×2), dry the organic phase with anhydrous sodium sulfate, evaporate the solvent to obtain R-2-ethyl benzenesulfonate propionate.

[0032] 2) Add 30g of ether, 4.38g (0.03mol) of sodium p-methoxyphenate, 0.32g (0.001mol) of tetra-n-butylammonium bromide into a 250mL two-necked flask, and then add R-2-benzenesulfonate dropwise into the flask A mixture of 7.74 g (0.03 mol) of ethyl propionate and 20 g of diethyl ether was refluxed for 20 hours.

[0033] 3) Then add 1.5g of sodium hydroxide and 15mL of water to the solution, reflux for hydrolysis, spot the plate to track the reaction, after the hydrolysis is complete, distill off ether at 30°C, collect the water phase and adjust the pH of the water phase to about 2...

Embodiment 3

[0035] 1) Add 14.69g (0.072mol) of p-ethylbenzenesulfonyl chloride, 9.90g (0.075mol) of D-n-propyl lactate, and 30mL of toluene into a 150mL two-necked flask, add 11.4g of triethylamine dropwise, and react for 12 hours to complete the reaction . Filter, wash with water (30mL×2), dry the organic phase with anhydrous sodium sulfate, and distill off the solvent to obtain R-2-(4-ethylbenzenesulfonate)propyl propionate.

[0036] 2) Add 30g of dichloromethane, 4.38g (0.03mol) of sodium p-methoxyphenate, 0.32g (0.001mol) of tetra-n-butylammonium bromide into a 250mL two-necked flask, and then add R-2- 9.00 g (0.03 mol) of (4-ethylbenzenesulfonate) propyl propionate, and 20 g of dichloromethane. Heated and refluxed for 20 hours.

[0037]3) Then add 1.5g sodium hydroxide to the solution, reflux for hydrolysis, spot the plate to track the reaction, after the hydrolysis is complete, adjust the pH of the solution to about 2 with dilute hydrochloric acid solution, separate the liquids, a...

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Abstract

The invention discloses a preparation method of S-2-(4-methoxyphenoxy) sodium propionate serving as a high optically-active sweet inhibitor. The preparation method comprises the steps of reacting D-substituted lactate with substituted benzene sulfonyl chloride to generate a corresponding R-substituted sulfonyl lactate; then reacting the obtained R-substituted sulfonyl lactate with p-methoxy phenate in a solvent to generate S-2-(4-methoxyphenoxy) propionate; and hydrolyzing and acidifying the obtained ester, and then reacting with an alkali containing sodium ions, thus obtaining the S-2-(4-methoxyphenoxy) sodium propionate. The preparation method of the S-2-(4-methoxyphenoxy) sodium propionate is developed for the first time. The obtained S-2-(4-methoxyphenoxy) sodium propionate has high optical purity; and when being measured by a sense method, the S-2-(4-methoxyphenoxy) sodium propionate has a better sweet inhibiting effect on sucrose compared with raceme, and can reduce the metabolic burden of R-type non-active ingredients of the raceme in human bodies and eliminate potential harm to the human bodies.

Description

technical field [0001] The invention relates to a method for preparing a sweetness inhibitor, in particular to a method for preparing a highly optically active sweetness inhibitor S-2-(4-methoxyphenoxy)sodium propionate. Background technique [0002] As an important basic raw material in food, sugar not only provides sweet taste, but also has other functions such as antisepsis, color enhancement, dispersion, bonding and shaping. However, when sugar is added in a large amount in food, it will cause the food to be too sweet and too greasy. The emergence of sweet taste inhibitors has solved this problem. They can compete with sweeteners to bind to sweet taste receptors on taste bud cells, reducing the sweetness of food without affecting other functions of sugars. [0003] Sodium 2-(4-methoxyphenoxy)propionate (SPMP) was first discovered in coffee beans as a sweetness inhibitor, and is currently widely used in beverages, condiments, flavored foods, baked foods, and grain produc...

Claims

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Application Information

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IPC IPC(8): C07C59/68C07C51/41
CPCC07C51/412C07C59/68
Inventor 江洪梁春杰马济美曾贞刘彬
Owner HUAZHONG AGRI UNIV
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