CN112876354B - 2- (4-methoxyphenoxy) propionic acid derivative with sweet taste inhibiting effect and industrial production method thereof - Google Patents
2- (4-methoxyphenoxy) propionic acid derivative with sweet taste inhibiting effect and industrial production method thereof Download PDFInfo
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- CN112876354B CN112876354B CN202110181948.1A CN202110181948A CN112876354B CN 112876354 B CN112876354 B CN 112876354B CN 202110181948 A CN202110181948 A CN 202110181948A CN 112876354 B CN112876354 B CN 112876354B
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- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
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- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/39—Addition of sweetness inhibitors
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- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
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Abstract
The invention discloses a 2- (4-methoxyphenoxy) propionic acid derivative with a sweet taste inhibiting effect and an industrial production method thereof. The structural general formula is as follows, wherein R represents C1‑C4Alkyl of (C)1‑C4Alkoxy, nitro or halogen atom of (A), X represents a hydrogen atom or C1‑C3Alkyl group of (1). Mixing p-methoxy substituted phenol, 2-ethyl 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 the organic phase to obtain an ester compound; adding the obtained ester and sodium hydroxide into ethanol, carrying out reflux reaction, and carrying out acidification, extraction, recrystallization and other steps to obtain the 2- (4-methoxyphenoxy) propionic acid derivative. The derivative is a brand-new sweet taste inhibiting compound, has a good sweet taste inhibiting effect on sucrose, and is mild in reaction condition, simple in separation and purification and high in product purity, and the temperature is not more than 100 ℃.
Description
Technical Field
The invention belongs to the technical field of food science, and particularly relates to a 2- (4-methoxyphenoxy) propionic acid derivative with a sweet taste inhibiting effect and an industrial production method thereof.
Background
Saccharides hold a great deal of importance in the food field. In addition to imparting sweetness and energy, carbohydrates improve product texture, providing flavor, color, and a slimy mouthfeel characteristic, as well as being a natural preservative and a sticking agent. To fully exploit these beneficial processing characteristics, the amount of sugars added is often very high, easily resulting in an unacceptably sweet, greasy mouthfeel. The emergence of a class of compounds with sweetness inhibiting effects has made the problem of "over-sweetness" in foods readily apparent. The sweet inhibitor can control sweetness without reducing saccharide consumption by blocking sweet receptor, and ensure important functional properties of saccharide in food.
2- (4-methoxyphenoxy) propionic acid, which is currently the most commonly used sweetness inhibitor, is a natural substance present in coffee beans and can also be synthesized chemically. 2- (4-methoxyphenoxy) propionic acid has high safety, has obvious sweet suppression effect on various natural or artificial sweeteners such as sucrose, fructose, glucose, sorbitol, saccharin sodium, aspartame and the like, and is usually used in an amount of one to five parts per million. It can effectively improve sweetness of high-sugar food such as moon cake, chocolate, candy, preserved fruit, etc., but has obvious sour taste at high addition amount.
The research on the sweet taste inhibition characteristic of the 2- (4-methoxyphenoxy) propionic acid derivative is relatively blank at present. It is known that the derivative obtained by structurally modifying 2- (4-methoxyphenoxy) propionic acid has a high-level sweet taste suppressing effect and is less likely to cause less sour taste stimulation. The applicant previously explored a series of different structurally modified 2- (4-methoxyphenoxy) propionic acid derivatives, and found that not all derivatives had sweet taste suppressing effects. For example, by modifying the carboxylic acid chain of 2- (4-methoxyphenoxy) propionic acid, the sweetness inhibitory effect of the derivative of interest is significantly lost.
The preparation of 2- (4-methoxyphenoxy) propionic acid has been studied for a long time at home and abroad, but the preparation of derivatives thereof is rarely reported. Yangyefeng et al (fine petrochemicals, 2016, 33 (02): 77-80) report a process for the synthesis of 2- (4-methoxyphenoxy) propionic acid from 2-chloropropionic acid and p-methoxyphenol under the action of sodium hydroxide and a reducing agent, with high yields, but at reaction temperatures as high as 135 ℃; chinese patents CN201410110984.9 and CN 200910273148.1 have performed the synthesis of 2- (4-methoxyphenoxy) propionic acid under relatively mild conditions using water or anhydrous ethanol as a reaction solvent, but the present applicant has found that the synthesis of 2- (4-methoxyphenoxy) propionic acid derivatives based on the existing patent methods is difficult to dissolve the reaction raw materials, has low yield or low purity of the reaction products, is mostly an oily mixture, and is inconvenient to separate and purify.
Disclosure of Invention
In view of the above-mentioned shortcomings of the prior art, the present invention provides a novel 2- (4-methoxyphenoxy) propionic acid derivative with sweet taste suppressing effect and its industrial production method. The derivative is a brand-new sweet taste inhibiting compound, partial compounds have weaker sour taste stimulation compared with 2- (4-methoxyphenoxy) propionic acid, the reaction conditions of the provided industrial production method are relatively mild, the reaction temperature is not more than 100 ℃, the separation and purification are simple, the product purity is higher, and the obtained derivative is expected to be used as a novel sweet taste inhibitor to improve the sweetness of high-sugar foods such as moon cakes, chocolates, candies, preserves and the like.
The specific technical scheme of the invention is as follows:
the 2- (4-methoxyphenoxy) propionic acid derivative with the sweet taste inhibiting effect has the following chemical general formula:
wherein R represents a group C1-C4Alkyl of (C)1-C4Alkoxy, nitro or halogen atoms;
the group represented by X is a hydrogen atom or C1-C3Alkyl group of (1).
An industrial production method of 2- (4-methoxyphenoxy) propionic acid derivatives having sweet taste inhibitory effect, comprising the steps of:
(1) mixing p-methoxy substituted phenol, 2-ethyl bromoalkanoate and potassium carbonate according to the molar ratio of 1 (1-1.3) to 1.1-1.5, stirring and heating in a solvent dimethylformamide for reacting for 8-15 h, cooling after the reaction is finished, and filtering; adding water and an organic phase into the filtrate, standing for layering to remove dimethylformamide, and distilling the collected organic layer to obtain an ester compound;
(2) mixing the ester compound and sodium hydroxide in the step (1) according to a molar ratio of 1 (1-1.8), adding the mixture into ethanol, performing reflux reaction for 3-8 h, distilling to remove the solvent, dissolving the obtained solid with water, and adding an acidic solution to adjust the pH value to 1-2; extracting the acidified mixture with diethyl ether, adding saturated Na2CO3Extracting and collectingAdjusting the pH value of the finally collected water layer to 1-2 by using an acidic solution in the organic layer, standing, separating out solids, and filtering to obtain a crude product;
(3) and recrystallizing the crude product, separating and crystallizing, and drying to obtain the target compound.
The reaction formula is as follows:
in order to further achieve the object of the present invention,
preferably, the volume ratio of the water to the organic phase in step (1) is 1: (1-1.5).
Preferably, the reaction temperature in the step (1) is preferably 50-80 ℃.
Preferably, the organic phase in step (1) is toluene, ethyl acetate, n-heptane, dichloromethane.
Preferably, the mass ratio of the ester compound to the ethanol in the step (2) is 1 (4-10).
Preferably, the reflux reaction temperature in the step (2) is preferably 80-90 ℃.
Preferably, the acidic solution in step (2) is a hydrochloric acid or sulfuric acid solution.
More preferably, the mass concentration of the hydrochloric acid or sulfuric acid solution is preferably 10-40%.
Preferably, the solvent for recrystallization in step (3) is methanol, ethanol, n-propanol or isopropanol.
Compared with the prior art, the invention has the following advantages:
1. the 2- (4-methoxyphenoxy) propionic acid derivative with the sweet taste inhibiting effect is provided, the target derivative is a brand new sweet taste inhibiting compound, and part of the compound has weaker sour stimulation compared with 2- (4-methoxyphenoxy) propionic acid and can be used as a novel sweet taste inhibitor for improving sweet and greasy taste caused by overhigh sweetness;
2. the industrial production method with relatively mild reaction conditions is provided, a polar aprotic solvent dimethylformamide is used for promoting the reaction, and the reaction temperature is not higher than 100 ℃;
3. the separation and purification steps are simple, multiple purification treatments such as extraction, recrystallization and the like are carried out, and the purity of the target product is higher (the purity is more than or equal to 95%).
Detailed Description
The present invention is further illustrated by the following examples, which should not be construed as limiting the scope of the invention.
Example 1
Preparation of 2- (3, 4-dimethoxyphenoxy) propionic acid
(1) 10kg of 3, 4-dimethoxyphenol, 14kg of ethyl 2-bromopropionate, 13kg of potassium carbonate and 150L of dimethylformamide were added to a reaction vessel, and the reaction was stirred at 70 ℃ for 11 hours. After the reaction, the mixture was cooled and filtered. Adding 400L of water and 500L of n-heptane into the filtrate, standing for layering, and distilling the collected organic layer to obtain ethyl 2- (3, 4-dimethoxyphenoxy) propionate;
(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 ℃ for 3 hours, the solvent was distilled off. The obtained solid was dissolved in water, and a hydrochloric acid solution having a mass concentration of 30% was added to adjust the pH to 2. Extracting the acidified mixture with diethyl ether, adding saturated Na2CO3The collected organic layer was extracted. And adjusting the pH value of the finally collected water layer to 2 by using a hydrochloric acid solution with the mass concentration of 30%, standing, separating out solids, and filtering to obtain a crude product of the 2- (3, 4-dimethoxyphenoxy) propionic acid.
(3) Recrystallizing the crude product with ethanol solution, separating crystal, and drying to obtain white solid 2- (3, 4-dimethoxyphenoxy) propionic acid with purity of not less than 95%.
(4)1H NMR(600MHz,CDCl3) δ 6.75(d,1H, J ═ 8.7Hz),6.58(d,1H, J ═ 2.8Hz),6.36(dd,1H, J ═ 8.7,2.9Hz),4.73(q,1H, J ═ 6.8Hz),3.84(d,6H, J ═ 9.7Hz),1.65(d,3H, J ═ 6.9 Hz). The sweetness inhibition rate of 0.15 per mill 2- (3, 4-dimethoxyphenoxy) propionic acid on 20 percent of sucrose solution is 30.5 percent, and the sour taste value is 5.0.
Example 2
Preparation of 2- (2-chloro-4-methoxyphenoxy) propionic acid
(1) 10kg of 2-chloro-4-methoxyphenol, 14kg of ethyl 2-bromopropionate, 13kg of potassium carbonate and 150L of dimethylformamide were added to a reaction vessel, and the reaction was stirred at 70 ℃ for 11 hours. After the reaction, the mixture was cooled and filtered. Adding 400L of water and 500L of n-heptane into the filtrate, standing for layering, and distilling the collected organic layer to obtain ethyl 2- (2-chloro-4-methoxyphenoxy) propionate;
(2) the obtained ethyl 2- (2-chloro-4-methoxyphenoxy) propionate and 3kg of sodium hydroxide were added to 90kg of ethanol, and after reflux reaction at 85 ℃ for 3 hours, the solvent was distilled off. The obtained solid was dissolved in water, and a hydrochloric acid solution having a mass concentration of 30% was added to adjust the pH to 2. Extracting the acidified mixture with diethyl ether, adding saturated Na2CO3The collected organic layer was extracted. Adjusting the pH value of the finally collected water layer to 2 by using a hydrochloric acid solution with the mass concentration of 30%, standing, separating out solids, and filtering to obtain a crude product of 2- (2-chloro-4-methoxyphenoxy) propionic acid;
(3) recrystallizing the crude product with ethanol solution, separating, crystallizing, and drying to obtain white solid 2- (2-chloro-4-methoxyphenoxy) propionic acid with purity of not less than 95%.
(4)1H NMR(600MHz,CDCl3) δ 6.97-6.92 (m,2H),6.74(dd,1H, J ═ 9.0,3.0Hz),4.69(q,1H, J ═ 6.9Hz),3.77(s,3H),1.68(d,3H, J ═ 6.9 Hz). The sweetness inhibition rate of 0.15 per mill 2- (2-chloro-4-methoxyphenoxy) propionic acid on 20 percent of sucrose solution is 32.7 percent, and the sour taste value is 3.4.
Example 3
2- (4-methoxy-2-methylphenoxy) acetic acid
(1) 10kg of 2-methyl-4-methoxyphenol, 14kg of ethyl 2-bromoacetate, 13kg of potassium carbonate and 150L of dimethylformamide were added to a reaction vessel, and the reaction was stirred at 70 ℃ for 11 hours. After the reaction, the mixture was cooled and filtered. Adding 400L of water and 500L of n-heptane into the filtrate, standing for layering, and distilling the collected organic layer to obtain ethyl 2- (4-methoxy-2-methylphenoxy) acetate;
(2) adding the obtained ethyl 2- (4-methoxy-2-methylphenoxy) acetate and 3kg sodium hydroxide into 90kg ethanol, refluxing at 85 deg.C for 3 hr, and distillingThe solvent was removed. The obtained solid was dissolved in water, and a hydrochloric acid solution having a mass concentration of 30% was added to adjust the pH to 2. Extracting the acidified mixture with diethyl ether, adding saturated Na2CO3The collected organic layer was extracted. Adjusting the pH value of the finally collected water layer to 2 by using a hydrochloric acid solution with the mass concentration of 30%, standing, separating out solids, and filtering to obtain a crude product of the ethyl 2- (4-methoxy-2-methylphenoxy) acetate;
(3) recrystallizing the crude product with ethanol solution, separating, crystallizing, and drying to obtain light yellow solid 2- (4-methoxy-2-methylphenoxy) acetic acid with purity not less than 95%.
(4)1H NMR(600MHz,CDCl3) δ 6.75(dd,1H, J ═ 3.0,0.9Hz),6.70(d,1H, J ═ 8.8Hz), 6.67-6.64 (m,1H),4.63(s,2H),3.76(s,3H),2.27(s, 3H). The sweetness inhibition rate of 0.15 per mill 2- (4-methoxy-2-methylphenoxy) acetic acid to 20 percent of sucrose solution is 32.3 percent, and the sour taste value is 3.5.
Comparative example
2- (4-methoxyphenoxy) propionic acid
2- (4-methoxyphenoxy) propionic acid was prepared according to patent CN 200910273148.1, example 2, and the sweetness inhibition ratio of 0.15 ‰ 2- (4-methoxyphenoxy) propionic acid on 20% sucrose solution was 34.1%, and the sour taste value was 5.1.
The compounds described in the examples have a similar sweetness-inhibiting effect as 2- (4-methoxyphenoxy) propionic acid, but a less sour taste stimulus than 2- (4-methoxyphenoxy) propionic acid.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (10)
1. The application of the 2- (4-methoxyphenoxy) propionic acid derivative with sweet taste inhibition effect in serving as a sweet taste inhibitor of weak sour taste is characterized in that the 2- (4-methoxyphenoxy) propionic acid derivative with sweet taste inhibition effect is 2- (2-chloro-4-methoxyphenoxy) propionic acid and 2- (4-methoxy-2-methylphenoxy) acetic acid.
2. The use according to claim 1, characterized in that the preparation process of the 2- (4-methoxyphenoxy) propionic acid derivative with sweet taste suppressing effect comprises the following steps:
(1) mixing p-methoxy substituted phenol, 2-ethyl bromoalkanoate and potassium carbonate according to the molar ratio of 1 (1-1.3) to 1.1-1.5, stirring and heating in a solvent dimethylformamide for reacting for 8-15 h, cooling after the reaction is finished, and filtering; adding water and an organic phase into the filtrate, standing for layering to remove dimethylformamide, and distilling the collected organic layer to obtain an ester compound;
(2) mixing the ester compound and sodium hydroxide in the step (1) according to a molar ratio of 1 (1-1.8), adding the mixture into ethanol, performing reflux reaction for 3-8 h, distilling to remove the solvent, dissolving the obtained solid with water, and adding an acidic solution to adjust the pH value to 1-2; extracting the acidified mixture with diethyl ether, adding saturated Na2CO3Extracting the collected organic layer, adjusting the pH of the finally collected water layer to 1-2 by using an acidic solution, standing, separating out solids, and filtering to obtain a crude product;
(3) and recrystallizing the crude product, separating and crystallizing, and drying to obtain the target compound.
3. Use according to claim 2, wherein the volume ratio of water to organic phase in step (1) is 1: (1-1.5).
4. The use according to claim 2, wherein the temperature of the reaction in step (1) is 50 to 80 ℃.
5. Use according to claim 2, wherein in step (1) the organic phase is toluene, ethyl acetate, n-heptane, dichloromethane.
6. The use of claim 2, wherein the mass ratio of the ester compound to the ethanol in the step (2) is 1 (4-10).
7. The use according to claim 2, wherein the temperature of the reflux reaction in step (2) is 80-90 ℃.
8. The use according to claim 2, wherein the acidic solution of step (2) is a hydrochloric acid or sulfuric acid solution.
9. The use according to claim 8, wherein the hydrochloric acid or sulfuric acid solution has a mass concentration of 10-40%.
10. Use according to any one of claims 2 to 9, wherein the solvent for recrystallization in step (3) is methanol, ethanol, n-propanol or isopropanol.
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