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Efficient anti-bacterial hydroxy acid ester oligomer

a hydroxy acid ester and oligomer technology, applied in the field of biomedicine, can solve the problems of complicated post-treatment process, high cost of raw materials used in the synthesis process, narrow application range, etc., and achieve the effect of broadening the application range, good water solubility, and high antibacterial efficiency

Pending Publication Date: 2022-04-14
ZHEJIANG ENMAT BIOLOGICAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention is a bio-based anti-bacterial agent with a rationally designed molecular structure that maximizes its ability to penetrate bacteria and destroy their cell membrane, resulting in high efficiency. The invention also regulates its hydrophilicity and hydrophobicity to create a water-soluble or water-insoluble anti-bacterial agent that can be used in various fields. The raw materials used in the invention are all bio-based, easy to obtain, and the synthesis process avoids the use of toxic catalysts and solvents, which means no complicated post-processing is needed and the catalyst can be recycled. The invention is conducive to scaling up and producing and also conducive to meeting environmental protection requirements and reducing production costs.

Problems solved by technology

The anti-bacterial activity of the above-mentioned oligomers is not high enough to meet the growing performance requirements for anti-bacterial products; and water solubility of the above-mentioned oligomers is not adjustable, resulting in a narrow application range.
In addition, the raw materials used in the synthesis process are expensive and are not biological-based material butyrolactone.
Toxic catalysts and solvents are also used, resulting in complicated post-treatment processes.

Method used

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  • Efficient anti-bacterial hydroxy acid ester oligomer
  • Efficient anti-bacterial hydroxy acid ester oligomer
  • Efficient anti-bacterial hydroxy acid ester oligomer

Examples

Experimental program
Comparison scheme
Effect test

embodiment 1

R-(−)-3-hydroxybutyrate Ethyl Ester Oligomer

embodiment 1-1

[0028]Adding 10 g of 3-hydroxybutyrate ethyl ester and 0.01 g of zinc acetate (i.e. a mass ratio of 3-hydroxybutyrate ethyl ester is 0.1%) in a three-necked flask with mechanical stirring, a thermometer and a distillation device, wherein a stirring speed is approximately 150 revolutions; under an environment with a trace of nitrogen, increasing a temperature to 150° C. with a speed of 0.5-3° C. / min to react for 1 hour, then stopping reaction to obtain a 3-HB oligomer; detecting a degree of polymerization by a mass spectrometry, wherein an anti-bacterial experiment refers to GB / T 20944.3-2008 Textiles—Evaluation for anti-bacterial activity—Part 3: Shake flask method, a strain used is Escherichia coli ATCC 25922.

embodiments 1-2 and 1-3

[0029]According to Table 1, catalyst types and reaction temperatures are changed on the basis of the embodiment 1-1, while other conditions are the same as those of the embodiment 1-1 to obtain the R-(−)-3-hydroxybutyrate ethyl ester oligomers with different polymerization degrees.

TABLE 1Experimental conditions and product parameters of embodiments 1-1, 1-2 and 1-3ReactionDegree ofAnti-temperatureReactionpolymerizationbacterialCatalyst(° C.)time (h)(n)SolubilityPurityrate (%)1-10.1% zinc15012-3water-100%99acetatesoluble1-20.1% zinc20024-8water-100%99acetateinsoluble1-30.1%15012-3water-100%99tetrabutylsolubletitanate

[0030]FIG. 1 is a mass spectrometry result of a water-soluble R-(−)-3-hydroxybutyrate ethyl ester oligomer according to embodiment 1-1.

[0031]FIG. 2 is a mass spectrometry result of a water-insoluble R-(−)-3-hydroxybutyrate ethyl ester oligomer embodiment 1-2.

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Abstract

An efficient anti-bacterial hydroxy acid ester oligomer of the present invention has a general structural formula (I). Starting from the design of molecular structure, the present invention rationally designs the end group and chain length structure of the substance of formula (I), and controls its clogP value, so that the substance of formula (I) of the present invention reaches an appropriate size, which maximizes the ability of the substance of formula (I) to penetrate into the bacteria and destroy the bacterial cell membrane, thereby achieving high anti-bacterial efficiency. By precisely designing the molecular structure, the present invention regulates the hydrophilicity and hydrophobicity of the hydroxy acid ester oligomer to obtain a bio-based anti-bacterial agent with controllable water solubility.

Description

CROSS REFERENCE OF RELATED APPLICATION[0001]The present invention claims priority under 35 U.S.C. 119(a-d) to CN 202111137059.1, filed Sep. 27, 2021; and CN202011155869.5, filed Oct. 26, 2020.BACKGROUND OF THE PRESENT INVENTIONField of Invention[0002]The present invention relates to a technical field of biomedicine, and more particularly to an efficient anti-bacterial hydroxy acid ester oligomer.Description of Related Arts[0003]Anti-bacterial agents refer to substances which keep the growth or reproduction of certain microorganisms (bacteria, fungi, yeasts, algae, viruses, etc.) below a certain level within a certain period of time. Anti-bacterial agents are widely used in textiles, plastics, detergents, medical supplies and other fields.[0004]With the continuous improvement of living standards, the hygienic requirements for textiles and various household plastics are also getting higher and higher. The continuous improvement of natural and environmental protection standards for ant...

Claims

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Application Information

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IPC IPC(8): A61K31/22
CPCA61K31/22C07C69/675A01N37/36A01P1/00A01P3/00A61P31/04C07C69/68Y02A50/30
Inventor CHEN, XUEJUNZHOU, GUOMIN
Owner ZHEJIANG ENMAT BIOLOGICAL TECH CO LTD
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