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WO-2026095678-A1 - ANTIBACTERIAL, ANTIFUNGAL, AND ANTIVIRAL COMPOSITION COMPRISING 2-OXOACETIC ACID (CAA-21), 3-HYDROXYPROPIONALDEHYDE HYBRID SYSTEM (HA-31M), 3,3-DIETHOXY-1-PROPENE (MAR-31), OR MIXTURE THEREOF, AND METHOD FOR PREPARING SAME

WO2026095678A1WO 2026095678 A1WO2026095678 A1WO 2026095678A1WO-2026095678-A1

Abstract

The present invention relates to an antibacterial, antifungal, and antiviral composition comprising 2-oxoacetic acid (CAA-21), 3-hydroxypropionaldehyde hybrid system (HA-31M), 3,3-diethoxy-1-propene (MAR-31), or a mixture thereof, and a preparation method therefor. The antibacterial, antifungal, and antiviral composition according to the present invention has low toxicity to the human body, is environmentally friendly, and exhibits a remarkably superior biocidal (disinfection) effect against various microorganisms [bacteria (including spores), fungi, and viruses]. Furthermore, the mixture has the characteristic of simultaneously exerting biocidal (disinfection) effects against various microorganisms.

Inventors

  • LEE, SANG HYUP
  • PARK, SOO KYUNG
  • KANG, HYE KYOUNG
  • PARK, SUNG YONG
  • YANG, Ha Hyun
  • JEONG, Hyoung Jin
  • LEE, GA HEE
  • KIM, YEON JI
  • PARK, SE MI
  • CHO, HYUN SUNG
  • LIM, YOO JIN
  • KIM, CHO RONG
  • KIM, YE EUN
  • SON, HYE MIN
  • JEONG, YU RA
  • CHOE, NONG HOON
  • KIM, Joo Soeng

Assignees

  • 덕성여자대학교 산학협력단
  • 건국대학교 산학협력단
  • (주)그린제약

Dates

Publication Date
20260507
Application Date
20251030
Priority Date
20241030

Claims (12)

  1. An antibacterial, antifungal, and antiviral composition comprising 2-oxoacetic acid of Formula 1 (CAA-21), 3-hydroxypropionaldehyde hybrid system of Formula 2 (HA-31M), 3,3-diethoxy-1-propene of Formula 3 (MAR-31), or a mixture thereof. [Chemical Formula 1] [Chemical Formula 2] [Chemical Formula 3]
  2. In paragraph 1, The above composition is an antibacterial, antifungal, and antiviral composition having antibacterial activity against one or more bacteria selected from the group consisting of Salmonella Typhimurium, Escherichia coli , Staphylococcus aureus , Pseudomonas aeruginosa , and Bacillus subtilis , and their spores.
  3. In paragraph 2, The above composition is an antibacterial, antifungal, and antiviral composition having sterilizing activity against Bacillus subtilis spores.
  4. In paragraph 1, The above composition is an antibacterial, antifungal, and antiviral composition having antifungal activity against one or more fungi selected from the group consisting of Aspergillus brasiliensis , Candida albicans, and Penicillium funiculosum .
  5. In paragraph 1, The above composition is an antibacterial, antifungal, and antiviral composition having antiviral activity against avian influenza virus MS96/1996 (H9N2).
  6. In paragraph 1, An antibacterial, antifungal, and antiviral composition comprising 2-oxoacetic acid (CAA-21) of the above chemical formula 1, wherein the composition is a 0.01% to 5% aqueous solution.
  7. In paragraph 1, An antibacterial, antifungal, and antiviral composition comprising the 3-hydroxypropionaldehyde hybrid system (HA-31M) of Chemical Formula 2 above is an aqueous solution of 0.5% to 5%.
  8. In paragraph 1, An antibacterial, antifungal, and antiviral composition comprising 3,3-diethoxy-1-propene (MAR-31) of the above chemical formula 3, wherein the composition is a 0.01% to 2% aqueous solution.
  9. In paragraph 1, A composition for antibacterial, antifungal, and antiviral properties, wherein the mixture of 2-oxoacetic acid (CAA-21) of Formula 1 and 3-hydroxypropionaldehyde hybrid system (HA-31M) of Formula 2, the mixture of 2-oxoacetic acid (CAA-21) of Formula 1 and 3,3-diethoxy-1-propene (MAR-31) of Formula 3, and the mixture of 3-hydroxypropionaldehyde hybrid system (HA-31M) of Formula 2 and 3,3-diethoxy-1-propene (MAR-31) of Formula 3 are each mixed in a ratio of 3:1 to 1:3.
  10. A method for preparing an antibacterial, antifungal, and antiviral composition comprising 2-oxoacetic acid (CAA-21) of the following chemical formula 1, (a) a step of placing glyoxal of the following chemical formula 4 into a reaction vessel with concentrated hydrochloric acid (c-HCl) and sodium nitrite ( NaNO2 ) and heating; (b) adding concentrated nitric acid ( HNO₃ ) to the reaction product of step (a) and heating; (c) a step of adding hydrogen peroxide ( H₂O₂ ) to the reaction product of step (b) and heating, adding manganese dioxide ( MnO₂ ) and stirring until bubble generation stops after the reaction is finished , and then removing the remaining hydrogen peroxide; and (d) a method comprising the step of stirring the reaction product of step (c) above, removing solids by filtration to obtain a product in the form of a clear aqueous solution, and further obtaining a final aqueous solution product of high concentration (50%) [2-oxoacetic acid (CAA-21) of Formula 1 below] by low-pressure concentration in a concentrator. [Chemical Formula 1] [Chemical Formula 4]
  11. A method for preparing an antibacterial, antifungal, and antiviral composition comprising a 3-hydroxypropionaldehyde hybrid system (HA-31M) of the following chemical formula 2, (a) a step of adding 3,3-diethoxy-1-propanol of the following chemical formula 5 and 2N H₂SO₄ to a reaction vessel and stirring for 60 minutes at 5°C or below to terminate the reaction; (b) adding CaCO3 to the solution obtained in step (a) and adjusting the pH to neutral 6.0-7.5; and (c) a method comprising the step of stirring the solution obtained in step (b) at 5°C or lower for 60 minutes, then filtering the reaction solution under reduced pressure using a diaphragm pump (~130 mbar) to obtain a mixture, and then diluting the resulting mixture with distilled water to a concentration of 10% to obtain a final product in the form of an aqueous solution of Formula 2 below [an antibacterial, antifungal, and antiviral composition comprising the 3-hydroxypropionaldehyde hybrid system (HA-31M) of Formula 2 below]. [Chemical Formula 2] [Chemical Formula 5]
  12. A method for preparing an antibacterial, antifungal, and antiviral composition comprising 3,3-diethoxy-1-propene (MAR-31) of the following chemical formula 3, (a) a step of adding copper sulfate ( CuSO₄ ), water, and dimethyl sulfoxide (DMSO) to a reaction vessel, adding allyl bromide of the following chemical formula 6, heating the reaction mixture, diluting it with distilled water, extracting it with diethyl ether, collecting the organic layer, drying it with calcium chloride ( CaCl₂ ), and concentrating it under reduced pressure to obtain allyl alcohol of the following chemical formula 7; (b) a step of adding pyridinium chlorochromate (PCC) and CH₂Cl₂ to a reaction vessel, adding the allyl alcohol of Formula 7 obtained in step (a) and CH₂Cl₂ under stirring, and stirring at room temperature until the reaction is complete, thereby obtaining propenal of Formula 8; and (c) a method comprising the step of reacting the propenal of Formula 8 obtained in step (b) above with ethanol and a catalyst of p-toluenesulfonic acid (PTSA, p-TsOH) in a diethyl ether solvent to obtain a final product in the form of a clear aqueous solution [an antibacterial, antifungal, and antiviral composition comprising 3,3-diethoxy-1-propene (MAR-31) of Formula 3 below]. [Chemical Formula 3] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8]

Description

A composition for antibacterial, antifungal, and antiviral use comprising 2-oxoacetic acid (CAA-21), 3-hydroxypropionaldehyde hybrid system (HA-31M), 3,3-diethoxy-1-propene (MAR-31), or a mixture thereof, and a method for preparing the same The present invention relates to an antibacterial, antifungal, and antiviral composition comprising 2-oxoacetic acid (CAA-21), 3-hydroxypropionaldehyde hybrid system (HA-31M), 3,3-diethoxy-1-propene (MAR-31), or a mixture thereof, and a method for preparing the same. Humans are exposed to numerous microorganisms in their daily lives, and some bacteria, fungi, and viruses cause various infections in the human body. Due to the risks associated with bacterial, fungal, and viral diseases, a variety of chemical products with antibacterial, antifungal, and antiviral activities are being released. Due to the increased use of surgical equipment resulting from recent advancements in medical technology and the COVID-19 pandemic, the demand for sterilization and disinfection products is increasing, and the market for biocides and disinfectants is continuously growing. Disinfectants used as biocides must satisfy strict conditions, such as broad-spectrum sterilization efficacy, rapid efficacy, maintenance of product stability, and low toxicity to the human body. Although many biocides and disinfectants have been developed and marketed to date, issues regarding safety and toxicity are constantly being raised. In particular, glutaraldehyde (GA), which is currently the most widely used substance in Korea, has already been banned from use in the healthcare sector in Europe and is expected to be banned in Korea soon as well, creating an urgent need for the development of alternative substances. Through in-depth research, the inventors have devised 2-oxoacetic acid (CAA-21), 3-hydroxypropionaldehyde hybrid system (HA-31M), 3,3-diethoxy-1-propene (MAR-31), or mixtures thereof that have low toxicity to the human body, are environmentally friendly, and have a simultaneous killing effect against various microorganisms (bacteria, bacterial spores, fungi, and viruses). Instead of using separate disinfectants for each microorganism, they have discovered a biocide capable of simultaneously eradicating various microorganisms (bacteria, bacterial spores, fungi, and viruses) with a single product, and it is expected that this will lead to the development of a groundbreaking product in this field. Figure 1 shows the antibacterial effect of glutaraldehyde (GA) at different concentrations (0.05% to 2%) against Salmonella Typhimurium . Figure 2 shows the antibacterial effects of glutaraldehyde (GA) and 2-oxoacetic acid (CAA-21) at different concentrations (0.25% to 2%) against Salmonella Typhimurium. Figure 3 shows the antibacterial effects of glutaraldehyde (GA) and 3-hydroxypropionaldehyde hybrid system (HA-31M) at different concentrations (0.5%–2.5%) against Salmonella Typhimurium . Figure 4 shows the antibacterial effects of 2-oxoacetate (CAA-21) at different concentrations (0.25%–1%) against Escherichia coli, Staphylococcus aureus , Pseudomonas aeruginosa , and Bacillus subtilis . Figure 5 shows the antibacterial effects of the 3-hydroxypropionaldehyde hybrid system (HA-31M) at different concentrations (0.5%–2.5%) against Escherichia coli, Staphylococcus aureus , Pseudomonas aeruginosa , and Bacillus subtilis . Figure 6 shows the antibacterial effects of a 2% glutaraldehyde (GA) solution and a 2% 2-oxoacetic acid (CAA-21) solution against Salmonella Typhimurium , Escherichia coli , Staphylococcus aureus , Pseudomonas aeruginosa , and Bacillus subtilis . Figure 7 shows the antibacterial effects of a 2% glutaraldehyde (GA) solution and a 2% 3-hydroxypropionaldehyde hybrid system (HA-31M) solution against Salmonella Typhimurium , Escherichia coli , Staphylococcus aureus , Pseudomonas aeruginosa , and Bacillus subtilis . Figure 8 shows the antibacterial effects of a 2% glutaraldehyde (GA) solution and a 2% 2-oxoacetic acid (CAA-21) solution on the spores of Bacillus subtilis . Figure 9 shows the antibacterial effect of a 2% glutaraldehyde (GA) solution and a 2% 3-hydroxypropionaldehyde hybrid system (HA-31M) solution on the spores of Bacillus subtilis . Figure 10 shows the antibacterial effect of 3,3-diethoxy-1-propene (MAR-31) at different concentrations (0.25% to 2%) against Salmonella Typhimurium. Figure 11 shows the antibacterial effects of 3,3-diethoxy-1-propene (MAR-31) at different concentrations (0.25–1%) against Escherichia coli, Staphylococcus aureus , Pseudomonas aeruginosa , and Bacillus subtilis . Figure 12 shows the antibacterial effect of a 2% solution of 3,3-diethoxy-1-propene (MAR-31) against Escherichia coli, Staphylococcus aureus , and Pseudomonas aeruginosa . Figure 13 shows the antibacterial effect of a 2% solution of 3,3-diethoxy-1-propene (MAR-31) on the spores of Bacillus subtilis . Figure 14 shows glutaraldehyde (GA) at different concentrations (0.01%–2%) for Aspergillus brasili