N-phenylglycine CAS 103-01-5
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N-phenylglycine CAS 103-01-5

N-phenylglycine CAS 103-01-5

Product Code: BM-2-1-405
CAS number: 135884-31-0
Molecular formula: C9H14BNO4
Molecular weight: 211.02
EINECS number: /
MDL No.: MFCD01318939
Hs code: 29339900
Main market: USA, Australia, Brazil, Japan, Germany, Indonesia, UK, New Zealand , Canada etc.
Manufacturer: BLOOM TECH Xi’an Factory
Technology service: R&D Dept.-4

 

N-phenylglycine (Anilinoacetic Acid), CAS 103-01-5, molecular formula C8H9NO2, is a chemical with the appearance of a yellow powder. Soluble in hot water and ethanol, slightly soluble in ether, easily soluble in alkaline solution. Its alkali metal salts are easily soluble in water, while calcium salts are difficult to dissolve in water. It is an amino acid compound commonly used as a basic chemical reagent for organic synthesis and as a raw material for chemical production. It is mainly used for structural modification and synthesis of glycine functional organic molecules such as indigo dye. In addition, this substance can be used for the determination of copper metal in the field of biochemical analysis.

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N-phenylglycine | Shaanxi BLOOM Tech Co., Ltd

CAS 103-01-5 | Shaanxi BLOOM Tech Co., Ltd

Chemical Formula

C9H14BNO4

Exact Mass

211.10

Molecular Weight

211.02

m/z

211.10 (100.0%), 210.11 (24.8%), 212.10 (9.7%), 211.11 (2.4%)

Elemental Analysis

C, 51.23; H, 6.69; B, 5.12; N, 6.64; O, 30.33

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N-phenylglycine, an important organic compound, plays a crucial role in various fields such as chemistry, medicine, and dyes. Its unique chemical structure and properties make it have a wide range of application prospects.

The key intermediate for manufacturing indigo dye

 

 

Indigo dye is a blue dye with a long history, widely used in industries such as textiles and printing and dyeing. In the synthesis process of indigo dye, it plays a crucial role. As a key intermediate, it can be converted into a precursor of indigo dye through a specific chemical reaction pathway.

Specifically, under alkaline conditions, it reacts with specific oxidants to produce intermediate products with indigo dye structure. These intermediate products can be further chemically treated to obtain indigo dyes with bright colors and good stability. Due to the introduction of this substance, the synthesis process of indigo dye is more efficient and environmentally friendly, while also improving the quality of the dye.

In addition, the application in the synthesis of indigo dye has also promoted technological progress and innovation in the dye industry. With people's increasing attention to environmental protection and sustainable development, as one of the important raw materials for environmentally friendly dyes, its market demand will continue to grow.

Sensitive indicator for colorimetric determination of copper

 

 

It also has a wide range of applications in the field of biochemical analysis. Especially in the process of colorimetric determination of copper, N, as a sensitive indicator, can accurately and quickly determine the copper content in the sample.

Colorimetry is an analytical method that determines the content of a substance based on its color change. In the process of measuring copper, the substance undergoes a specific chemical reaction with copper ions to produce compounds with specific colors. The color change of this compound is linearly related to the concentration of copper ions, so the copper content can be indirectly determined by measuring the color change of the compound.

As an indicator for colorimetric determination of copper, it has the following advantages:

Firstly

It has high sensitivity and can accurately determine the trace copper content in the sample;

01

Secondly

It is easy to operate, without the need for complex instruments and equipment or tedious experimental steps;

02

Thirdly

It has good accuracy, stable and reliable measurement results, and is not affected by interference from other ions.

03

Therefore

It has been widely applied in the field of biochemical analysis.

04

Multi functional raw materials for manufacturing other organic compounds

 

 

In addition to the above-mentioned uses, it can also be used as a multifunctional raw material for manufacturing other organic compounds. Its unique chemical structure and properties enable it to undergo chemical reactions with various compounds, generating organic compounds with specific structures and properties.

For example, it can undergo cyclization condensation reaction with carbon monoxide to generate N-heterocyclic lactone compounds. These lactone compounds have potential application value in fields such as organic synthesis and drug development. In addition, it can also undergo condensation, substitution and other reactions with other compounds to generate organic compounds with specific functional groups. These compounds also have broad application prospects in fields such as chemical industry and materials science.

The anti biofilm mechanism of N-phenylglycine

Biofilm is a complex population structure composed of microbial cells and their secreted extracellular polymeric substances (EPS), which can adhere to biological or non biological surfaces. In the medical field, biofilm is a key factor that makes many chronic infections difficult to cure, such as lung infections, wound infections, and medical device related infections. It can protect microorganisms from attacks by the host immune system and antibiotics, significantly reducing the efficacy of antibiotics and increasing the difficulty and cost of treatment. In the industrial field, biofilms can form on surfaces such as pipelines, ships, and food processing equipment, leading to issues such as equipment corrosion, blockage, and decreased product quality. Therefore, developing effective anti biofilm strategies has important theoretical and practical significance. N-phenylglycine is an organic compound containing a benzene ring and an amino group, which has been found to have certain anti biofilm activity in recent years.

The formation process and characteristics of biofilm

The formation process of biofilm
 

The formation of biofilm is a dynamic and multi-stage process, mainly including the following steps:

 

Reversible attachment stage: Free microbial cells reversibly attach to the surface of an object through weak interaction forces such as van der Waals forces and electrostatic attraction. The attachment at this stage is temporary, and cells are prone to return to a free state.

 

Irreversible attachment stage: Microbial cells begin to secrete some adhesion molecules, such as pili, cilia, etc., which make the cell more firmly bound to the surface and form irreversible attachment. At the same time, the characteristics of the cell surface change, laying the foundation for subsequent population growth and biofilm formation.

 

Microcystis formation stage: Irreversible attached cells begin to proliferate, forming tiny colonies. These microcolonies communicate and coordinate with each other through signaling molecules, gradually forming an ordered population structure.

 

Mature stage of biofilm: With the continuous growth and fusion of microcolonies, the biofilm gradually matures. Mature biofilms have complex three-dimensional structures composed of microbial cells EPS, Composed of water channels and other components. EPS is mainly composed of polysaccharides, proteins, nucleic acids, and lipids, which provide a protective microenvironment for microbial cells and help them resist external environmental pressure.

 

The diffusion stage of biofilm: Some cells in mature biofilm will be released from the biofilm, becoming free cells and starting a new biofilm formation cycle, or spreading to other parts to cause new infections.

Characteristics of Biofilms
 

Structural complexity: Biofilms have a complex three-dimensional structure, with uneven distribution of microbial cells and EPS at different levels, forming tiny ecological niches. This structure enables microbial cells within the biofilm to collaborate and adapt to environmental changes together.

 

Drug resistance: Microbial cells in biofilms have significantly increased resistance to antibiotics compared to free cells. On the one hand, EPS can block the penetration of antibiotics, making it difficult for antibiotics to reach the interior of microbial cells; On the other hand, microbial cells within the biofilm are in different physiological states, with some cells in a dormant state and insensitive to antibiotics.

 

Anti host immunity: Biofilms can evade recognition and attack by the host immune system. EPS can mask the antigenic epitopes of microbial cells and prevent the binding of immune cells to microbial cells. Meanwhile, microbial cells within the biofilm can secrete some immunosuppressive factors to suppress the host immune response.

The anti biofilm mechanism of N-phenylglycine

N-phenylglycine use | Shaanxi BLOOM Tech Co., Ltd

Inhibition of initial attachment of biofilm

 

The initial attachment of biofilm is the crucial first step in biofilm formation. N-phenylglycine can inhibit the initial attachment of microbial cells to object surfaces in various ways. N-phenylglycine can interact with certain components on the surface of microbial cells, altering the charge distribution and hydrophobicity of the cell surface, thereby reducing the affinity between the cell and the surface of the object, and reducing the occurrence of reversible and irreversible adhesion. For example, research has found that N-phenylglycine can bind to lipopolysaccharides on the surface of bacterial cells, altering the surface charge properties and making it difficult for bacterial cells to adhere to solid surfaces. The adhesion molecules on the surface of microbial cells play an important role in the initial adhesion process. N-phenylglycine can regulate the expression of related genes in microbial cells, inhibit the synthesis and secretion of adhesion molecules. Through real-time quantitative PCR and Western blot analysis, it was found that bacteria treated with N-phenylglycine showed a significant decrease in the expression levels of adhesion molecules such as pili and cilia, thereby reducing their ability to attach to surfaces.

Interference group sensing system

 

Quorum sensing is a mechanism through which microbial cells secrete and perceive signaling molecules to exchange information and coordinate group behavior, playing a key role in the formation, development, and maturation of biofilms. N-phenylglycine can interfere with the microbial quorum sensing system, thereby inhibiting the formation of biofilms. Many microorganisms initiate quorum sensing by synthesizing specific signaling molecules, such as acyl homoserine lactones (AHLs), self inducing peptides (AIPs), etc. N-phenylglycine can inhibit the activity of enzymes related to signal molecule synthesis or regulate the expression of related genes, reducing the synthesis of signal molecules. There are receptor proteins for signaling molecules on the surface of microbial cells. When signaling molecules bind to receptor proteins, they activate downstream signaling pathways and regulate the expression of related genes. N-phenylglycine can compete with signaling molecules to bind to receptor proteins, or alter the conformation of receptor proteins to prevent them from sensing signaling molecules properly, thereby blocking the transduction of quorum sensing signals.

N-phenylglycine use | Shaanxi BLOOM Tech Co., Ltd
N-phenylglycine use | Shaanxi BLOOM Tech Co., Ltd

Destruction of biofilm structure

 

N-phenylglycine can exert its anti biofilm effect by disrupting the structure of already formed biofilms. EPS is an important component of biofilm structure, and N-phenylglycine can activate certain enzymes in microbial cells or biofilms, such as polysaccharide hydrolases, proteases, etc., to degrade polysaccharides, proteins, and other components in EPS, disrupting the stable structure of biofilms. For example, research has found that N-phenylglycine can induce Pseudomonas aeruginosa to secrete alginate lyase, which degrades the alginate components in the biofilm, making the structure of the biofilm loose and easy to remove. The hydration state of biofilm has a significant impact on its structure and function. N-phenylglycine can affect the distribution and fluidity of water in biofilms, altering their hydration state. Through techniques such as magnetic resonance imaging, it was observed that the internal moisture content and flowability of biofilms treated with N-phenylglycine changed, leading to structural damage and loss of function.

Affects the metabolism of microorganisms

 

N-phenylglycine can affect the metabolic processes of microorganisms, thereby inhibiting the formation and development of biofilms. The energy metabolism of microorganisms is an important foundation for maintaining their growth and biofilm formation. N-phenylglycine can inhibit the activity of respiratory chain enzymes or key enzymes in the glycolysis pathway within microbial cells, interfering with microbial energy production. For example, in Escherichia coli, N-phenylglycine can inhibit the activity of cytochrome oxidase, reduce ATP synthesis, and deprive microbial cells of sufficient energy to maintain biofilm formation and stability. Microorganisms need to absorb nutrients from their surrounding environment to maintain growth and biofilm formation. N-phenylglycine can affect the expression and activity of nutrient transporters on microbial cell membranes, regulating microbial uptake of nutrients such as carbon, nitrogen, and phosphorus sources. Research has found that bacteria treated with N-phenylglycine have a reduced ability to uptake nutrients such as glucose and amino acids, which affects bacterial growth and biofilm formation.

N-phenylglycine use | Shaanxi BLOOM Tech Co., Ltd

 

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