Shaanxi BLOOM Tech Co., Ltd. is one of the most experienced manufacturers and suppliers of ethyl acetamidoacetate cas 1906-82-7 in China. Welcome to wholesale bulk high quality ethyl acetamidoacetate cas 1906-82-7 for sale here from our factory. Good service and reasonable price are available.
Ethyl acetamidoacetate is an important organic synthetic intermediate. Its appearance is usually a colorless to pale yellow liquid or a low-melting-point white solid. The molecular structure of this compound combines amide and ester groups, as well as a reactive methylene group, making its chemical properties extremely diverse - it can be used as an acylation reagent, and the methylene group is more prone to form a carbon anion under the action of strong bases, thereby undergoing alkylation, condensation and other nucleophilic reactions. This compound is widely used in the fields of medicine, pesticides and fine chemicals, especially often used in the synthesis of heterocyclic compounds (such as pyrazoles, imidazoles), and is also a key building block for constructing quinolone antibiotics and vitamin A. Industrial production is mostly obtained by acetylation of ethyl glycinate hydrochloride, and its unique reactivity and versatility make it an indispensable molecular tool in modern organic synthesis.
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Chemical Formula |
C6H11NO3 |
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Exact Mass |
145.07 |
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Molecular Weight |
145.16 |
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m/z |
145.07 (100.0%), 146.08 (6.5%) |
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Elemental Analysis |
C, 49.65; H, 7.64; N, 9.65; O, 33.07 |
Ethyl acetamidoacetate has a wide range of applications, mainly as a pharmaceutical intermediate, and has shown important application value in fields such as pharmaceuticals and chemical engineering.
Pharmaceutical intermediates
Production of anti leptospira drugs
Can be used to produce ethyl imidazolate, which is an effective anti leptospira drug. Leptospirasis is an animal borne infectious disease caused by pathogenic Leptospira, and its key role in the preparation of such drugs makes it of great significance in the treatment of Leptospirasis.
Non steroidal anti-inflammatory drugs
It also exhibits the characteristics of nonsteroidal anti-inflammatory drugs. By blocking the activation of cyclooxygenase, the conversion of arachidonic acid to prostaglandin E2 and other inflammatory mediators can be reduced, thereby lowering body temperature and relieving pain. This makes it potentially valuable in treating symptoms such as fever and headache.
Chemical raw materials
Fine chemical raw materials
As an amino acid derivative, it is an important fine chemical raw material. It can be used to synthesize various chemicals with specific functions, such as surfactants, dye intermediates, etc. These chemicals have a wide range of applications in industries such as textiles, printing and dyeing, and daily chemical products.
Synthesize other compounds
It can also be converted into other valuable compounds through further chemical reactions. For example, it can undergo ester exchange reactions with alcohol compounds to generate compounds with different ester based structures; It can also undergo amidation reaction with amine compounds to generate amide compounds, etc. These compounds have broad application prospects in the field of chemical engineering.
Scientific research
Biomedical research
Due to its anti-inflammatory, antipyretic, analgesic and other biological activities, it has become an important research object in biomedical research. Scientists can provide theoretical and experimental basis for the development of new drugs by studying their mechanisms of action, metabolic pathways, etc.
Drug screening and evaluation
It can also serve as a tool for drug screening and evaluation. By comparing the effects of different compounds on their biological activity, drug candidates with better efficacy and lower side effects can be screened. This helps accelerate the process of new drug development and improve the success rate of drug research and development.
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mechanism of action
Inhibit the growth and reproduction of Leptospira
Ethyl acetamidoacetate or its derivatives are considered to exert a potent inhibitory effect on the growth and reproduction of pathogenic Leptospira, mainly by interfering with the key metabolic pathways essential for the survival of Leptospira. Specifically, these compounds may target and inhibit critical biological processes of Leptospira, including DNA synthesis, RNA transcription, or protein translation-three core links that support the proliferation and inheritance of Leptospira. For instance, in the process of DNA synthesis, they may bind to key enzymes such as DNA polymerase or topoisomerase of Leptospira, which are responsible for catalyzing DNA replication and strand separation. This binding event leads to a significant decrease or complete loss of enzyme activity, thereby blocking the normal replication of Leptospira DNA and preventing the formation of new daughter cells.
Similarly, interference with RNA transcription may hinder the synthesis of messenger RNA (mRNA), while inhibition of protein translation may disrupt the assembly of ribosomes and the synthesis of functional proteins required for Leptospira metabolism. Overall, such interference with metabolic pathways disrupts the orderly progress of Leptospira's life activities, ultimately suppressing its growth and reproduction and limiting the spread of the pathogen in the host.
Disrupting the cellular structure of Leptospira
In addition to inhibiting metabolic pathways, acetylglycine ethyl ester or its derivatives may also achieve direct bactericidal effects on Leptospira by disrupting the integrity of its cellular structure, which is crucial for maintaining the survival and normal function of Leptospira. The cellular structure of Leptospira, including the cell membrane, cell wall, and cytoplasm, plays distinct and indispensable roles: the cell wall provides structural support and protects the cell from external pressure, the cell membrane regulates the exchange of substances between the cell and its environment, and the cytoplasm contains various organelles and biomolecules that participate in metabolic reactions. These compounds may interact specifically with the components of these cellular structures-for example, they may bind to lipopolysaccharides (LPS) on the cell wall of Leptospira or phospholipids in the cell membrane, destroying the stability of these components.
This destructive effect leads to damage to the integrity of the cell structure: the cell wall may become fragile and prone to rupture, the cell membrane may lose its permeability barrier function, resulting in the leakage of intracellular substances (such as electrolytes, proteins, and nucleic acids), and the cytoplasm may undergo denaturation or coagulation. Once the cellular structure is severely damaged, Leptospira can no longer maintain its normal physiological functions, leading to cell death and achieving the purpose of eliminating the pathogen.
Regulating host immune response
Beyond their direct inhibitory or bactericidal effects on Leptospira, acetylated glycine ethyl ester or its derivatives may also enhance the host's own defense capabilities against Leptospira infection by regulating the host's immune response, forming a "dual defense" mechanism. The host's immune system is the primary line of defense against pathogenic microorganisms, and its effective activation is crucial for clearing Leptospira. These compounds may act as immunomodulators to activate key immune cells of the host, including macrophages, T lymphocytes, and B lymphocytes.
Macrophages, as the first line of innate immunity, can phagocytose and degrade invading Leptospira after activation; T lymphocytes can differentiate into effector T cells to directly kill Leptospira-infected cells or regulate the immune response; B lymphocytes can proliferate and differentiate into plasma cells to secrete specific antibodies that bind to Leptospira, promoting its clearance by the immune system.In addition to activating immune cells, these derivatives may also regulate the secretion of host cytokines, such as interferon (IFN), tumor necrosis factor (TNF), and interleukins (ILs). Cytokines are important signaling molecules in the immune system: interferon can enhance the antiviral and antibacterial abilities of cells, tumor necrosis factor can promote the apoptosis of infected cells and the activation of immune cells, and interleukins can mediate the communication and coordination between immune cells. By regulating the balanced secretion of these cytokines, these compounds can enhance the overall immune response of the host, enabling the body to more effectively recognize and eliminate Leptospira, and reducing the severity of infection.
Interference with the pathogenic mechanism of Leptospira
Leptospira relies on multiple complex pathogenic mechanisms to invade the host, cause tissue damage, and establish infection, among which adhesion, invasion, and toxin production are the three most critical links. Acetylglycine ethyl ester or its derivatives may alleviate or prevent the damage of Leptospira to the host by specifically interfering with one or more of these pathogenic mechanisms, thereby reducing the pathogenicity of the pathogen. For example, in the adhesion stage, Leptospira needs to adhere to the surface of host cells (such as epithelial cells of the urinary tract or respiratory tract) through specific adhesion molecules to avoid being cleared by the host's immune system and physiological excretion.
These compounds may bind to the adhesion molecules on the surface of Leptospira or block the binding sites on host cells, thereby inhibiting the adhesion ability of Leptospira and preventing it from attaching to host cells. In the invasion stage, they may inhibit the secretion of invasive factors by Leptospira, which are necessary for the pathogen to penetrate the host cell membrane and enter the cell for reproduction and spread.By blocking invasion, they can limit the spread of Leptospira from the initial infection site to other tissues and organs. In addition, some Leptospira strains can secrete toxins (such as hemolysins and leptospiral immunoglobulin-like proteins) that damage host tissues and induce inflammatory responses. These derivatives may inhibit the synthesis or secretion of these toxins, reducing their direct damage to host cells and tissues, and alleviating the inflammatory response and pathological damage caused by infection.
Ethyl acetamidoacetate, a versatile organic compound with the chemical formula C6H11NO3, has undergone a fascinating journey from its initial discovery to its widespread application in various chemical industries. The compound was first synthesized in the late 19th century, marking a significant milestone in the field of organic chemistry.
The discovery process is attributed to the pioneering efforts of organic chemists who were intrigued by the potential of amido esters in synthetic reactions. Early researchers observed its unique reactivity and stability, which laid the groundwork for further exploration. Throughout the 20th century, advancements in analytical techniques and synthetic methodologies facilitated a deeper understanding of its chemical properties and reaction mechanisms.
The development accelerated during the mid-20th century, driven by its increasing demand in the production of pharmaceuticals, agrochemicals, and dyes. Its ability to serve as a key intermediate in the synthesis of complex molecules made it an indispensable component in the chemical industry.
What are the side effects of this compound?
Chemical properties and potential risks
Skin contact
This substance may have a certain degree of skin irritation. Long term or frequent skin contact may cause redness, swelling, pain, or burning sensation on the skin. Therefore, when handling this substance, appropriate protective gloves and clothing should be worn to avoid direct skin contact.
Eye contact
Similarly, it may have a stimulating effect on the eyes. Once the eyes come into contact with the substance, rinse immediately with plenty of water and seek medical assistance.
Inhalation
Although the vapor pressure of this substance is relatively low, prolonged exposure to high concentrations or enclosed environments may still cause irritation to the respiratory system. This may lead to symptoms such as coughing, dry throat, and shortness of breath. Therefore, when handling this substance, it is necessary to ensure good ventilation in the workplace and wear appropriate respiratory protective equipment.
Drug metabolism and potential toxicity
Liver metabolism and toxicity
Most drugs and chemicals require liver metabolism. Acetylglycine ethyl ester or its metabolites may exert a certain burden or toxic effects on the liver. Long term or excessive intake may lead to liver damage or dysfunction. Therefore, when using drugs containing acetyl glycine ethyl ester, close attention should be paid to the patient's liver function indicators, and liver function monitoring should be performed if necessary.
Renal excretion and toxicity
Acetylglycine ethyl ester or its metabolites may also be excreted through the kidneys. During the excretion process, they may have certain stimulating or toxic effects on the kidneys. This may lead to kidney damage or functional impairment. Therefore, when using relevant drugs, it is important to ensure that patients have sufficient urine output to promote drug excretion and closely monitor their renal function indicators.
Central nervous system effects
Although the effects of acetyl glycine ethyl ester on the central nervous system itself are not yet clear, some similar organic compounds may have inhibitory effects on the central nervous system at high concentrations. This may lead to symptoms such as headache, dizziness, nausea, vomiting, and fatigue. When using relevant medications, close attention should be paid to the patient's neurological symptoms and neurological assessments should be conducted if necessary.
The product quality and purity have been recognized
The purity of products provided by multiple suppliers reaches 99%, meeting the standards for pharmaceutical intermediates. Customers have reported that the appearance of the white crystalline powder and its stable physical properties (melting point 43-46℃, boiling point 260℃) meet the requirements of experiments and production. Some enterprises have established long-term cooperation due to the stable quality.
The application effect is outstanding
As a key intermediate for the anti-leptospira drug metacycline ethyl ester, customers evaluate its high synthesis efficiency and stable reaction activity. For example, some enterprises in Jiangsu reported that using this product can significantly increase the yield of the target drug and reduce by-products, simplifying the subsequent purification process.
The service and supply chain response is proactive
Suppliers generally provide flexible packaging (1kg to 25kg per barrel), rapid delivery (such as "deliverable nationwide" by Hubei Kowod Chemical), and technical consultation support. Enterprises like Wuhan Karnos Technology have been recommended by customers for their "transparent quotations and timely after-sales service". Some suppliers also offer customized synthesis services.
The cost-performance advantage is obvious
The price range is wide (5 yuan per gram to 2000 yuan per kilogram), and customers can choose gradient quotations based on their usage. Small and medium-sized research and development institutions tend to choose cost-effective suppliers, while large pharmaceutical enterprises pay more attention to the supplier's qualifications and stable supply capacity.
The convenience of storage and use is highly praised
The product has good stability at room temperature (shelf life 24 months), is compatible with various solvents (such as chloroform, DMSO), and customers evaluate it as "good solubility and simple operation". Some suppliers provide MSDS and operation guidelines to lower the usage threshold.
FAQ
What is the generic name for ethyl acetate?
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Ethyl acetate (also known as ethyl ethanoate, acetic acid ethyl ester, acetoxyethane, 1-acetoxyethane, EtOAC, ETAC, EA) is an organic ester compound with a molecular formula of C4H8O2. It is a colourless liquid with a fruity characteristic odour that is commonly recognised in glues and nail polish remover.
What is the formula for ethyl acetamide?
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Ethylacetamide | C4H9NO | CID 12253 - PubChem.
What does ethyl acetate do?
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Ethyl acetate (CASRN: 141-78-6) is an organic solvent widely used for different applications in manufacturing, pharmaceutical, or food industry, mainly as a solvent for paints and lacquers. It has flammable properties.
Is ethyl acetate toxic to humans?
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Is ethyl acetate toxic to humans?
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