P-aminobenzoic acid derivatives and their compositions and uses

A technology of p-aminobenzoic acid and its derivatives, which is applied in the fields of application, animal feed, sulfonate preparation, etc. It can solve the bottlenecks of the stability of feed biobiotics and production, sales, and management, and affect human reproductive performance and sexuality. symptoms, carcinogenicity, etc.

Active Publication Date: 2017-06-06
GUANGZHOU INSIGHER BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the stability, production, sales, and management of feed biobiotics are still bottlenecks and difficulties in promotion.
The long-term use of hormone feed additives not only damages the immune system of the animal itself, but also may affect the reproductive performance and sexual characteristics of humans and cause cancer.

Method used

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  • P-aminobenzoic acid derivatives and their compositions and uses
  • P-aminobenzoic acid derivatives and their compositions and uses
  • P-aminobenzoic acid derivatives and their compositions and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0115] Example 1 4-((E)-phenyleneimino)benzoic acid sodium salt

[0116]

[0117] In a 1L three-necked round-bottom flask, add 220 mL of 95% ethanol and 4.2 g of sodium hydroxide (96%, 100 mmol, 1 eq) in sequence, and stir mechanically until the sodium hydroxide dissolves. After the above sodium hydroxide solution was cooled to room temperature, 13.7g (100mmol, 1eq) of p-aminobenzoic acid was added, stirred and dissolved, and 13.2g (100mmol, 1eq) of 3-phenylacrolein was added, stirred overnight at room temperature to obtain a yellow suspension, TLC Monitor until the end of the reaction, filter with suction, wash the filter cake with 95% ethanol (30mL×3), and dry under reduced pressure at 55°C to obtain 12.6g of (4-((E)-phenyleneimino)benzoic acid sodium salt as a yellow powder solid ), yield 46.2%.

[0118] The NMR data of 4-((E)-phenyleneimino)benzoic acid sodium salt are as follows:

[0119] 1 H NMR (500MHz, DMSO-d 6 ): δ(ppm)8.39(d,J=9.0Hz,1H),7.83(d,J=8.0Hz,1H),7.67(d...

Embodiment 2

[0120] Example 2 4-(1,3-disulfonic acid phenylpropylamino)benzoic acid sodium salt (1:3)

[0121]

[0122] Add 200mL of water and 273.1g (100mmol, 1eq) of 4-((E)-phenylpropyleneimino)benzoic acid sodium salt into a 1L three-necked round-bottomed flask in turn, stir mechanically to disperse evenly, and add sodium bisulfite to the reaction solution 20.8g (200mmol, 2eq), stirred and reacted at room temperature for 8h to obtain a clear reaction solution. Add 200 mL of 95% ethanol to the obtained clarified reaction solution and stir at room temperature to obtain a white suspension, filter under reduced pressure, wash the filter cake with 95% ethanol (30 mL×3), and dry under reduced pressure at 55°C to obtain the target product as a white powder Solid (4-(1,3-disulfonic acid phenylpropylamino) benzoic acid sodium salt) 31.6g, yield 65.7%.

[0123] 1 H NMR (500MHz, DMSO-d 6 ): δ (ppm) 7.47 (d, J = 8.0Hz, 2H), 7.17 (m, 5H), 6.22 (d, J = 8.5Hz, 2H), 5.21 (d, J = 10.0Hz, 1H), 3.62...

Embodiment 3

[0124] Example 3 Potassium salt of 4-(1,3-disulfonic acid phenylpropylamino)benzoate (1:3)

[0125]

[0126] In a 1L three-necked round-bottomed flask, 220 mL of ethanol and 5.8 g of potassium hydroxide (96%, 100 mmol, 1 eq) were sequentially added, and mechanically stirred until the potassium hydroxide was dissolved. Add 13.7g (100mmol, 1eq) of p-aminobenzoic acid to the above potassium hydroxide solution, stir to dissolve, add 13.2g (100mmol, 1eq) of cinnamaldehyde, stir overnight at room temperature, a large amount of solids in the reaction solution precipitate to form a suspension, pump Filter and dry under vacuum at 40°C. The obtained product was dissolved in 200 mL of water, 24.0 g (200 mmol, 2 eq) of potassium bisulfite was added, and the reaction was stirred at room temperature for 8 h to obtain a clear reaction liquid. Add 1L of ethanol to the obtained clarified reaction solution and stir at room temperature to obtain a white suspension, filter under reduced press...

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PUM

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Abstract

The invention discloses para aminobenzoic acid derivatives and a composition and application thereof. The structure of the para aminobenzoic acid derivatives is shown in the formula (I). According to animal experiments, it is shown that the para aminobenzoic acid derivatives or the composition has a significant effect on promoting the growth of animals, and particularly weight increment and feed conversion efficiency are obviously changed. The para aminobenzoic acid derivatives or solvate thereof or the composition thereof can be used as feed additives in animal husbandry and be particularly applied as animal feeding growth promoters.

Description

[0001] Technical field: [0002] The present invention belongs to the field of organic chemistry, and specifically relates to p-aminobenzoic acid derivatives, their solvates, compositions containing the aforementioned compounds and their preparation methods, and also relates to the use of these compounds and compositions as feed additives in animal husbandry Uses, specifically as a growth promoter for feeding animals. [0003] Background technique: [0004] Growth promoter is one of the feed additives; the most basic requirements are safety, stability, palatability, no effect on reproductive performance, effectiveness, economy and convenience; the main function is to stimulate animal growth, improve animal health, improve Improve feed utilization, improve animal production capacity, save feed expenses, and reduce production costs. [0005] Animal growth promoters currently used in production include antibiotics, synthetic antibacterial drugs, hormones, enzyme preparations, and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C303/32C07C309/24A23K20/111
Inventor 彭险峰覃宗华
Owner GUANGZHOU INSIGHER BIOTECHNOLOGY CO LTD
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