Antibacterial preservative sorbic acid amino acid ester derivative and preparation method thereof

A technology for preservatives sorbic acid and amino acid ester, applied in the field of antibacterial preservatives, can solve problems such as weakening of bacteriostatic activity, and achieve the effects of simple and easy synthesis method, good application value and wide source of raw materials

Active Publication Date: 2016-01-06
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, sorbic acid can exert the greatest antibacterial activity only under acidic conditions, and its antibacterial activity is greatly weakened under neutral or alkaline conditions.

Method used

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  • Antibacterial preservative sorbic acid amino acid ester derivative and preparation method thereof
  • Antibacterial preservative sorbic acid amino acid ester derivative and preparation method thereof
  • Antibacterial preservative sorbic acid amino acid ester derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1, glycine ethyl sorbate shown in formula (Ⅳ) (a 1 ) preparation

[0036]

[0037] Synthesis of glycine ethyl ester hydrochloride: Add 30ml of ethanol to a 100ml three-neck flask, then add 2.6ml of SOCl dropwise 2 During the dropping process, the temperature is controlled at -10°C to 0°C. After the dropwise addition, continue to stir for 1 hour, then add 0.75 g of glycine, and naturally raise the temperature to room temperature for 3 hours. At this time, the solution becomes a white emulsion, and then heated to reflux 4h, until the solid disappears completely. Remove excess ethanol and SOCl under reduced pressure 2 After that, a light yellow viscous liquid was obtained.

[0038] Acyl chloride of sorbic acid: Add 1.12g sorbic acid and 2.18ml thionyl chloride into a 100ml three-necked flask, and continue stirring for 1h until no gas is generated. Excess SOCl was removed under reduced pressure 2 After that, a light yellow viscous liquid was obtained.

...

Embodiment 2

[0040] Embodiment 2, glycine propyl sorbate shown in formula (Ⅴ) (a 2 ) preparation

[0041]

[0042] Synthesis of glycine propyl ester hydrochloride: Add 30ml of n-propanol in a 100ml three-neck flask, then add 2.6ml of SOCl dropwise 2 During the dropping process, the temperature is controlled at -10°C to 0°C. After the dropwise addition, continue to stir for 1 hour, then add 0.75 g of glycine, and naturally raise the temperature to room temperature for 3 hours. At this time, the solution becomes a white emulsion, and then heated to reflux 4h, until the solid disappears completely. Remove excess ethanol and SOCl under reduced pressure 2 After that, a yellow viscous liquid was obtained.

[0043] Synthesis of propyl glycinate sorbate: Add the synthesized propyl glycinate hydrochloride into a 100ml three-neck flask, then add 10ml chloroform and 2ml triethylamine, after cooling in an ice-salt bath, slowly add acid chloride diluted with chloroform dropwise Sorbic acid solut...

Embodiment 3

[0044] Embodiment 3, glycine isopropyl sorbate shown in formula (Ⅵ) (a 3 ) preparation

[0045]

[0046] Synthesis of glycine isopropyl ester hydrochloride: Add 30ml of isopropanol to a 100ml three-neck flask, then add 2.6ml of SOCl dropwise 2 During the dropping process, the temperature is controlled at -10°C to 0°C. After the dropwise addition, continue to stir for 1 hour, then add 0.75 g of glycine, and naturally raise the temperature to room temperature for 3 hours. At this time, the solution becomes a white emulsion, and then heated to reflux 4h, until the solid disappears completely. Remove excess ethanol and SOCl under reduced pressure 2 After that, a yellow viscous liquid was obtained.

[0047] Synthesis of glycine isopropyl sorbate: add the synthesized glycine isopropyl hydrochloride into a 100ml three-necked flask, then add 10ml chloroform and 2ml triethylamine, cool in an ice-salt bath, slowly add dilute with chloroform Acyl chloride sorbic acid solution, the...

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Abstract

The invention belongs to the field of synthesis of a drug, and relates to a sorbic acid-amino acid ester derivate of an antimicrobial preservative and a preparation method thereof. The preparation method comprises the steps of: enabling amino acid and alcohol to react to generate amino-acid ester by utilizing an acyl chloride method, and then reacting with amino-acid ester by sorbic acid after acylating chlorination, so as to synthesize the amino acid ester derivate of the sorbic acid. The amino acid ester derivate of the novel compound sorbic acid obtained by the method has no sensitization on skin of a human body, is suitable for different pH systems with large ranges, has antibacterial broad-spectrum property and good potential application value, and can be used as the antimicrobial preservative applied to corrosion prevention and antibiosis of foods, drugs, cosmetics, pesticides, leather products and wood materials.

Description

technical field [0001] The invention relates to the field of antibacterial antiseptics, in particular to derivatives of amino acid sorbic acid esters of antibacterial antiseptics and a preparation method thereof. Background technique [0002] Bacteria, yeasts and molds can cause food spoilage and cause huge economic losses. The use of chemically synthesized preservatives is one of the most commonly used antiseptic methods at present. Sorbic acid and its sodium and potassium salts are widely used in food additives as preservatives to inhibit the growth of bacteria, yeasts and molds. However, sorbic acid can exert the greatest antibacterial activity only under acidic conditions, and its antibacterial activity is greatly weakened under neutral or alkaline conditions. Therefore it is necessary to find better antibacterial effect, more broad-spectrum and low toxicity antibacterial preservatives. Contents of the invention [0003] The object of the present invention is to ove...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C233/49C07C231/02A01P1/00A01P3/00
Inventor 韦庆益曾广翔
Owner SOUTH CHINA UNIV OF TECH
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