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Synthesis method of sweet taste inhibitor 2-(4- methoxyphenyl) sodium propionate

A methoxyphenoxy, sweet taste inhibitor technology, applied in the field of compound preparation, can solve the problem of low purity and the like

Inactive Publication Date: 2013-05-29
HUAZHONG AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

To overcome the large amount of impurities that exist in the 2-(4-methoxyphenoxy) sodium propionate prepared by existing methods, the defect that the purity is not high

Method used

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  • Synthesis method of sweet taste inhibitor 2-(4- methoxyphenyl) sodium propionate
  • Synthesis method of sweet taste inhibitor 2-(4- methoxyphenyl) sodium propionate
  • Synthesis method of sweet taste inhibitor 2-(4- methoxyphenyl) sodium propionate

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Embodiment 1 (control test)

[0015] Put 6.2g (50mmol) of p-methoxyphenol, 6.1g (55mmol) of 2-chloropropionic acid, 2.3g (58mmol) of sodium hydroxide, and 40mL of deionized water in a 100mL single-necked flask, heat and reflux for about 6h, and the reaction ends Afterwards, the pH was adjusted to 2.0 with food-grade hydrochloric acid to produce a large amount of viscous white solid, which was filtered to obtain 6.0 g of viscous white solid 2-(4-methoxyphenoxy)propionic acid. Productive rate 66.67%, product is mixture (see attached figure 1 shown). Then the resulting viscous 2-(4-methoxyphenoxy)propionic acid was dissolved in an equimolar sodium hydroxide aqueous solution, and after dissolution, the water was evaporated at 80°C to obtain the sweetness inhibitor 2-(4 -sodium methoxyphenoxy)propionate.

Embodiment 2

[0016] Embodiment 2 (the present invention)

[0017] 6.2g (50mmol) of p-methoxyphenol, 7.7g (55mmol) of ethyl 2-chloropropionate, and 8.0g (58mmol) of potassium carbonate. Catalyst potassium iodide 0.1g, absolute ethanol 40mL in a 100mL single-necked flask, heated to reflux for about 6 hours, until the reaction of ethyl 2-chloropropionate was basically complete by thin-layer chromatography, cooled, filtered, and the filtrate was distilled to recover ethanol. Add 50 mL of ethyl acetate and 60 mL of deionized water to the solid obtained from the above filtration, and statically separate the layers. Collect the water layer and adjust the water layer to a pH value of 2.0 with food-grade hydrochloric acid. A large amount of white solids are produced. Add ether to dissolve the Solid, 40 mL each time, extracted three times in total, then washed the collected ether layer twice with 20 mL of deionized water to remove residual potassium ions, evaporated the ether to obtain white solid 2...

Embodiment 3

[0018] Embodiment 3 (the present invention)

[0019] 6.2g (50mmol) of p-methoxyphenol, 7.7g (55mmol) of ethyl 2-chloropropionate, and 8.0g (58mmol) of potassium carbonate. Catalyst sodium iodide 0.1g, absolute ethanol 40mL in a 100mL single-necked flask, heated to reflux for about 6 hours, until the reaction of ethyl 2-chloropropionate was basically complete by thin-layer chromatography, cooled, filtered, and the filtrate was distilled to recover ethanol. Add 50 mL of ethyl acetate and 60 mL of deionized water to the solid obtained from the above filtration, and statically separate the layers. Collect the water layer and adjust the water layer to a pH value of 2.0 with food-grade hydrochloric acid. A large amount of white solids are produced. Add ether to dissolve the Solid, 40 mL each time, extracted three times in total, then washed the collected ether layer twice with 20 mL of deionized water to remove residual potassium ions, evaporated the ether to obtain white solid 2-(4...

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Abstract

The invention belongs to the field of compound preparation method, in particular relates to a synthesis method of sweet taste inhibitor 2-(4- methoxyphenoxy) sodium propionate. P-methoxyphenol and 2-Chloro Ethyl with the mol ratio of 1:1 to 1:1.2 are used as ingredients, and the potassium carbonate is used as aid-binding agent, and the mol ratio of potassium carbonate to P-methoxyphenol is 1:1-1:1.3. Potassium iodide or natriumiodide can be used as catalyst, with the mass thereof being 1%-5% that of the P-methoxyphenol. Absolute ethyl alcohol is used as solvent and the processes of reflex reaction, cooling, filtering, and filtrate distillation are conducted in sequence to reclaim ethyl alcohol. Thereafter, the obtained solid goes through the skimming treatment by Ethyl acetate and de-ionized water. The aqueous layer is collected and the PH thereof adjusted to 2.0 by food grade hydrochloric acid. Aether should be added to dissolve the solid in the queous layer, the aether layer then is distilled to obtain the white solid 2-(4- methoxyphenoxy) monoprop solid which is then dissolved into equimolar aqueous sodium hydroxide solution to be rotatably distilled to expluse water to obtain method of sweet taste inhibitor 2-(4- methoxyphenoxy) sodium propionate. The invention can effectively eliminate the impurities in the products to heighten the purity of the product.

Description

technical field [0001] The invention belongs to the technical field of compound preparation, in particular to a chemical synthesis method of 2-(4-methoxyphenoxy) sodium propionate, the compound 2-(4-methoxyphenoxy) sodium propionate is A sweet taste suppressant. Background technique [0002] On the one hand, sucrose can be used as a sweetener in food to increase the taste of food. At the same time, sucrose is also widely used as a food preservative, swelling agent, color enhancer, dispersant, etc. However, when sucrose is used as a food preservative, bulking agent, color enhancer, and dispersant, it is often too sweet due to the large amount added, resulting in an unpleasant taste. Therefore, the use of some sweet taste inhibitors that can reduce the sweetness without reducing the amount of sucrose is of great significance to alleviate the unpleasant taste caused by excessive use of sugar. [0003] Sodium 2-(4-methoxyphenoxy)propionate is a natural substance present in cof...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C59/64C07C51/41
Inventor 刘军安江洪张全魏晓磊
Owner HUAZHONG AGRI UNIV
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