2-(4-methoxyphenoxy) propionic acid derivative with sweetness inhibiting effect and industrial production method of 2-(4-methoxyphenoxy) propionic acid derivative

A technology of methoxyphenoxy and propionic acid derivatives, applied in the field of food science, can solve the problems of high yield, high reaction temperature, low yield and the like, and achieve the effect of simple separation and purification steps

Active Publication Date: 2021-06-01
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 Syn...

Method used

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  • 2-(4-methoxyphenoxy) propionic acid derivative with sweetness inhibiting effect and industrial production method of 2-(4-methoxyphenoxy) propionic acid derivative
  • 2-(4-methoxyphenoxy) propionic acid derivative with sweetness inhibiting effect and industrial production method of 2-(4-methoxyphenoxy) propionic acid derivative
  • 2-(4-methoxyphenoxy) propionic acid derivative with sweetness inhibiting effect and industrial production method of 2-(4-methoxyphenoxy) propionic acid derivative

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 a sweetness inhibiting effect and an industrial production method of the 2-(4-methoxyphenoxy) propionic acid derivative. The structural general formula is shown in the specification, in the formula, R represents C1-C4 alkyl, C1-C4 alkoxy, nitryl or halogen atoms, and X represents hydrogen atoms or C1-C3 alkyl. The preparation method comprises the following steps: mixing p-methoxy substituted phenol, ethyl 2-bromoalkanoate and potassium carbonate, reacting in dimethylformamide, and filtering; adding water and an organic phase into the filtrate, carrying out liquid separation treatment, and evaporating to remove the organic phase to obtain an ester compound; and adding the obtained ester and sodium hydroxide into ethanol, carrying out reflux reaction, acidifying, extracting, recrystallizing and the like to obtain the 2-(4-methoxyphenoxy) propionic acid derivative. The derivative is a brand-new sweetness inhibiting compound and has a good sweetness inhibiting effect on cane sugar, the industrial method is mild in reaction condition, the temperature does not exceed 100 DEG C, separation and purification are simple, and the product purity is high.

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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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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