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2-(4-methoxyphenoxy)propionic acid derivatives with sweet taste inhibitory effect and industrial production method thereof

A technology of methoxyphenoxy and propionic acid derivatives, which is applied in the field of food science, can solve the problems of high yield, difficult reaction raw materials, and low purity of reaction products, and achieve the effect of simple separation and purification steps

Active Publication Date: 2022-04-22
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Yang Yufeng et al. (Fine Petrochemical Industry, 2016, 33(02): 77-80) reported a synthesis of 2-(4- The method of methoxyphenoxy)propionic acid has high yield, but the reaction temperature is as high as 135°C; Chinese patent CN201410110984.9 and CN 200910273148.1 use water or absolute ethanol as the reaction solvent, and carry out under relatively mild conditions Synthesis of 2-(4-methoxyphenoxy)propionic acid, but the applicant found that, based on the existing patent method for the synthesis of 2-(4-methoxyphenoxy)propionic acid derivatives, the reaction The raw material is difficult to dissolve, the yield is low or the purity of the reaction product is low, mostly an oily mixture, which is inconvenient for separation and purification

Method used

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  • 2-(4-methoxyphenoxy)propionic acid derivatives with sweet taste inhibitory effect and industrial production method thereof
  • 2-(4-methoxyphenoxy)propionic acid derivatives with sweet taste inhibitory effect and industrial production method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Preparation of 2-(3,4-dimethoxyphenoxy)propionic acid

[0034] (1) Add 10kg of 3,4-dimethoxyphenol, 14kg of ethyl 2-bromopropionate, 13kg of potassium carbonate and 150L of dimethylformamide into the reaction vessel, and stir at 70°C for 11h. Cool and filter after the reaction. 400L of water and 500L of n-heptane were added to the filtrate, the layers were left to stand, and the collected organic layer was distilled to obtain ethyl 2-(3,4-dimethoxyphenoxy)propionate;

[0035] (2) The obtained ethyl 2-(3,4-dimethoxyphenoxy)propionate and 3kg of sodium hydroxide were added to 90kg of ethanol, and after reflux reaction at 85°C for 3h, the solvent was distilled off. The obtained solid was dissolved in water, and the pH was adjusted to 2 by adding hydrochloric acid solution with a mass concentration of 30%. The acidified mixture was extracted with ether, and saturated Na 2 CO 3 The collected organic layers were extracted. The pH of the finally collected water layer was ...

Embodiment 2

[0039] Preparation of 2-(2-chloro-4-methoxyphenoxy)propionic acid

[0040] (1) Add 10kg of 2-chloro-4-methoxyphenol, 14kg of ethyl 2-bromopropionate, 13kg of potassium carbonate and 150L of dimethylformamide into a reaction vessel, and stir at 70°C for 11 hours. Cool and filter after the reaction. 400L of water and 500L of n-heptane were added to the filtrate, the layers were left to stand, and the organic layer collected by distillation was obtained to obtain ethyl 2-(2-chloro-4-methoxyphenoxy)propionate;

[0041] (2) The obtained ethyl 2-(2-chloro-4-methoxyphenoxy)propionate and 3kg of sodium hydroxide were added to 90kg of ethanol, and after reflux at 85°C for 3h, the solvent was distilled off. The obtained solid was dissolved in water, and the pH was adjusted to 2 by adding hydrochloric acid solution with a mass concentration of 30%. The acidified mixture was extracted with ether, and saturated Na 2 CO 3 The collected organic layers were extracted. The final collected...

Embodiment 3

[0045] 2-(4-Methoxy-2-methylphenoxy)acetic acid

[0046] (1) Add 10kg of 2-methyl-4-methoxyphenol, 14kg of ethyl 2-bromoacetate, 13kg of potassium carbonate and 150L of dimethylformamide into a reaction vessel, and stir at 70°C for 11 hours. Cool and filter after the reaction. 400L of water and 500L of n-heptane were added to the filtrate, the layers were left to stand, and the collected organic layer was distilled to obtain ethyl 2-(4-methoxy-2-methylphenoxy)acetate;

[0047] (2) The obtained ethyl 2-(4-methoxy-2-methylphenoxy)acetate and 3kg of sodium hydroxide were added to 90kg of ethanol, and after reflux at 85°C for 3h, the solvent was distilled off. The obtained solid was dissolved in water, and the pH was adjusted to 2 by adding hydrochloric acid solution with a mass concentration of 30%. The acidified mixture was extracted with ether, and saturated Na 2 CO 3 The collected organic layers were extracted. Adjust the pH of the finally collected water layer to 2 with ...

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Abstract

The invention discloses a 2-(4-methoxyphenoxy) propionic acid derivative with sweetness inhibitory effect and an industrial production method thereof. Its structural formula is as follows, where R represents C 1 -C 4 Alkyl, C 1 -C 4 alkoxy, nitro or halogen atom, X represents a hydrogen atom or C 1 -C 3 of alkyl. Mix p-methoxy substituted phenol, ethyl 2-bromoalkanoate, and potassium carbonate, react in dimethylformamide, and filter; add water and organic phase to the filtrate, separate liquid, and evaporate the organic phase. Obtain an ester compound; add the obtained ester and sodium hydroxide to ethanol, reflux reaction, and obtain 2-(4-methoxyphenoxy)propionic acid derivatives through steps such as acidification, extraction, and recrystallization. The derivative of the present invention is a brand-new sweetness-inhibiting compound, which has good sweetness-inhibiting effect on sucrose. The industrial method has mild reaction conditions, the temperature does not exceed 100°C, simple separation and purification, and high product purity.

Description

technical field [0001] The invention belongs to the field of food science and technology, and in particular relates to a 2-(4-methoxyphenoxy)propionic acid derivative with a sweet taste inhibitory effect and an industrial production method thereof. Background technique [0002] Sugar occupies a pivotal position in the food field. In addition to imparting sweetness and energy, sugar can improve product texture, provide aroma, color and creamy mouthfeel characteristics, and is also a natural preservative and sticking agent. In order to give full play to these beneficial processing properties, the amount of sugar added is often very high, which can easily lead to an unacceptable sweet and greasy taste. The emergence of a class of compounds with sweetness inhibitory effect has solved the problem of "oversweetness" in food. Sweetness inhibitors can control the sweetness without reducing the amount of sugars by blocking the sweetness receptors, ensuring the important functional ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C59/68C07C59/70C07C51/09C07C51/42A23L27/30
CPCC07C59/68C07C59/70A23L27/39
Inventor 郑建仙邓雯婷
Owner SOUTH CHINA UNIV OF TECH
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