Acetohydroxamic Acid CAS 546-88-3

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Acetohydroxamic acid, white crystalline or crystalline powder (orange red for feed additive grade); Molecular formula C5H10N2O, CAS 80-73-9, almost odorless, with a slightly bitter taste. When exposed to light, it changes color and easily absorbs moisture. This product is easily soluble in water and anhydrous ethanol, and the aqueous solution exhibits an acidic reaction. This product is also known as ethoxyxam acid, which is used as a rumen microbial urease inhibitor in the feed industry and is used as a feed additive for ruminants. In addition, it is also a competitive urease inhibitor in medicine, marketed as Junshitong. In the metallurgical industry, it is used as a chelating agent and extractant for extracting and identifying metal ions.

Acetylhydroxamic acid (AHA) is an organic compound with a unique chemical structure, and its - CONHOH functional group endows it with a wide range of biological activities and chemical properties. From innovative treatments in the pharmaceutical field to efficiency improvements in agricultural production, from precision extraction in the metallurgical industry to breakthroughs in environmental protection technology, they are driving the coordinated development of multiple industries with their irreplaceable role.

Medical field: Breakthrough from stone dissolution to antibacterial treatment

 

1. Precise treatment of urinary tract stones and infections
It is a representative drug of competitive inhibitors of urease, and its mechanism of action is to form chelates with nickel atoms in urease, inactivating the enzyme and blocking the process of urea decomposition into ammonia and carbon dioxide. This characteristic makes it a core drug for treating infectious urinary tract stones:

Stone dissolution and prevention: In urinary tract infections, urease producing bacteria (such as Proteus mirabilis) break down urea to produce ammonia, leading to an increase in urine pH and the formation of magnesium ammonium phosphate and carbonate apatite stones. Acetylhydroxamic acid inhibits urease activity, restores normal pH of urine, and gradually dissolves, shrinks, or even disappears formed stones.

 

Clinical data shows that after medication, the urine ammonia concentration of patients decreases by 60% -80%, the urine pH value returns from alkaline (>7.5) to neutral (6.0-7.0), and the stone recurrence rate decreases by more than 50%.

Antibacterial synergistic effect: It can penetrate bacterial cell membranes, interfere with nucleotide metabolism, block deoxyribonucleic acid (DNA) biosynthesis, and has direct antibacterial activity against urease producing bacteria such as Klebsiella and Pseudomonas aeruginosa. When used in combination with antibiotics such as levofloxacin, it can shorten the course of treatment by 3-5 days and increase the bacterial clearance rate to over 95%.

 

Clinical indications:
Infectious urinary tract stones: As a first-line medication, it is used to treat ammonium magnesium phosphate stones (guano stones) caused by urease producing bacteria, especially suitable for patients with stone diameter<1.5cm and no severe urinary tract obstruction.
Chronic urinary tract infection: For recurrent urinary tract infections, inhibition of bacterial urease activity can reduce ammonia production, alleviate bladder irritation symptoms (such as frequent urination, urgency, and pain), and lower the recurrence rate of infection.
Long term catheter-related infections: For patients with indwelling catheters or bladder fistulas, the formation of biofilm on the surface of the catheter can be reduced, the risk of stone attachment can be lowered, and the lifespan of the catheter can be extended by 2-3 times.

 

2. Exploration of treatment for special diseases
Hepatic encephalopathy: In patients with cirrhosis, ammonia produced by the breakdown of proteins by intestinal bacteria is a key factor in inducing hepatic encephalopathy. By inhibiting intestinal urease activity and reducing ammonia absorption, the blood ammonia concentration decreased by 40% -60%, significantly improving the patient's cognitive function and neurological symptoms.
Tumor adjuvant therapy: Research has found that it can inhibit urease activity in tumor cells, block ammonia mediated alkalization of the tumor microenvironment, enhance sensitivity to chemotherapy drugs (such as cisplatin), and provide new strategies for comprehensive treatment of tumors.

Animal husbandry: Revolutionary improvement in ruminant nutrition

 

1. Core applications of rumen microbial urease inhibitors
Ruminant animals (such as cows and sheep) have a large number of urease producing microorganisms in their rumen, which can decompose urea or protein in feed into ammonia for the synthesis of microbial proteins. However, when the rate of ammonia production exceeds the microbial utilization capacity, it can lead to:
Ammonia poisoning: Elevated blood ammonia concentration can cause shortness of breath, muscle tremors, and even death.
Protein waste: About 30% of feed nitrogen is excreted in the form of ammonia, reducing protein utilization efficiency.
As an efficient urease inhibitor, it can specifically bind to the active center of urease, reducing enzyme activity by 80% -90%, thereby:

 

Optimize rumen ammonia environment: Maintain ammonia concentration within the optimal range for microbial protein synthesis (5-10mg/dL) to increase microbial protein production by 20% -30%.
Improving feed efficiency: Adding 0.5-1.0g/d acetohydroxamic acid to dairy cow feed can increase crude protein utilization by 15% -20%, reduce urinary nitrogen emissions by 40% -50%, and lower environmental pollution.
Enhance animal health: Reducing blood ammonia concentration can reduce ammonia stress, improve immunity, reduce the incidence rate of cow mastitis by 30%, and reduce the diarrhea rate of calves by 25%.

 

2. Optimization plan for modern dairy farming
With the popularization of high-yield dairy cows (daily milk production>35kg), their demand for dietary protein has significantly increased. The application can achieve:
Precise nutrition regulation: Adjust the amount of acetlydroxamic acid added (0.8-1.2g/d) according to the crude protein content of the diet (such as 16% -18% CP), reducing the fluctuation range of rumen ammonia concentration to ± 1mg/dL and stabilizing microbial protein synthesis.

 

Economic benefits improvement: With a 5% -10% increase in dietary costs, increasing protein utilization efficiency (synthesizing 10-15g of microbial protein per kilogram of dry matter) can increase the annual milk payment of each dairy cow by 2000-3000 yuan.
Significant environmental benefits: reducing urinary nitrogen emissions can lower ammonia concentration in farms by 30% -50%, improving animal welfare and the quality of the surrounding environment.

Acetohydroxamic acid synthesis route:

1. Synthesis and application of rumen microbial urease inhibitors:

Synthesis method: Chemical equation

HONH₃Cl+CH₃COOCH₂CH₃ CH₃CONHOH

The steps are:

Add equimolar amounts of hydroxylamine hydrochloride and ethyl acetate to the reactor;

Under continuous stirring, add 0.09 moles of concentrated hydrochloric acid, and then add concentrated hydrochloric acid drop by drop, accurately adjusting the pH of the reaction solution to 6.0;

⑶ Allow the reaction solution to continue stirring at room temperature for 2 hours until the reaction is complete;

Adding acetone to the reaction solution can accelerate the crystallization rate of acetyloximic acid and improve its purity;

(5) Rotary steaming, steaming to dryness

Collect dried crystals

2. Preparation process of acetyloximic acid:

Synthesis method: Chemical equation

NH₂OH·HCl+CH₃COOCH₃ -- CH₃CONHOH+CH₃OH+HCl

The steps are as follows: first, mix hydroxylamine hydrochloride and methyl acetate in a weight ratio of 1:1.1 and place them in a reaction vessel, requiring sealing. After containment, add solid sodium hydroxide as a catalyst to neutralize the hydrochloric acid brought in by hydroxylamine hydrochloride. The amount of solid sodium hydroxide added is 90% of the amount of hydrochloric acid brought in by hydroxylamine hydrochloride. Then, add methanol of the same volume as methyl acetate with a concentration of 80% as the solvent to the reaction vessel; The reaction can occur by controlling the reaction temperature at 30 ℃ and the pressure at 0.05Mpa.

3. Research on the Synthesis of Acetoxyxamic Acid:

Step: Add methanol, water, and hydroxylamine hydrochloride to a four necked bottle, then add ethyl acetate and sodium hydroxide solutions, control the temperature to fully react, add concentrated hydrochloric acid to precipitate sodium chloride from the system, vacuum concentrate the reaction mixture, extract with boiling ethyl acetate, add a few drops of acetone to the extraction solution, convert the partially reacted hydroxylamine hydrochloride into acetone oxime, concentrate the extraction solution, cool the mother liquor, and filter through suction, The crystal was dried in vacuum at 65 ℃ for 4 hours to obtain the finished product.

4. Synthesis of Acetohydroxamic Acid and Determination of Stability Constants of Its Complexes with Pu (IV), NP (IV)

Step: First, synthesize sodium hydroxamate in two steps, followed by acidification and recrystallization for purification.

(1) The preparation of sodium hydroxamate was carried out by adding 15ml of distilled water and 12ml of ethanol to a 250ml round bottom flask. Under stirring, dry 0.1mol (7g) of hydroxylamine hydrochloride was added in batches to completely dissolve it. After the solution is completed, remove the ice bath and add 0.1mol of ethyl acetate dropwise under continuous stirring to thoroughly mix. The solution was stirred at room temperature for 1-2 hours and then added to an ice bath for cooling.

(2) Preparation and purification of ethyl hydroxamic acid: Under continuous stirring, slowly add concentrated hydrochloric acid and adjust to the endpoint pH=6 (the solution becomes turbid at the endpoint, which is due to the precipitation of NaCl from ethanol). Spin steam at 50 ℃, evaporate until yellow viscous sediment appears, stop evaporation, add 100ml of anhydrous ethanol, mix well, and continue to evaporate until almost dry.

Dissolve the crystals in the flask twice with 200ml of boiling ethyl acetate, pour out the solution, and add a few drops of analytically pure acetone to the warm solution under stirring to convert the unreacted hydroxylamine hydrochloride into acetoxime (acetoxime has a high solubility in cold ethyl acetate and does not precipitate during the crystallization process of hydroxamic acid and remains in the solution). The dissolved solution is heated, boiled and concentrated until turbidity appears, and then Free cooling to room temperature before being put into the freezer overnight.

Filter to obtain transparent crystals. Wash with cold ethyl acetate. The yield is 60%, and the purity is greater than 97%.

Analysis of the Production Status and Enterprises of Acetoxyxamic Acid in China:
There are more than 10 enterprises engaged in acetyloxime acid industry in China, with a relatively scattered distribution. From the existing statistics of enterprises, it can be seen that acetyloximic acid enterprises are mostly distributed in coastal areas, central regions, and southwestern regions, and there are also scattered enterprises.

In terms of specific provinces, Guangdong, Yunnan, Jiangsu and other provinces occupy an advantageous position.
As the market for acetyloxime acid heats up, more and more enterprises are joining the market competition, and the distribution of enterprises will also be diversified, but the above distribution characteristics will not change.

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