About This Product:
CAS Number : 104-03-0
Molecular Weight : 181.15
Molecular Formula : C8H7NO4
Synonym(s) : 2-(4-NITROPHENYL)ACETIC ACID;
: 4-NITRO-A-TOLUIC ACID;
: 4-NITROBENZENEACETIC ACID;
: Para Nitro Phenyl Acetic Acid;
: 4-Nitrophenylacetic;
: 4-Nitrobenzencacetic;Nitro-a-toluic acid;
: p-Nitro-α-toluicacid;Nitrophenylacetic acid
Appearance : Off white to light yellow color soli
Purity : >98.00% (HPLC)
Melting Point : 152°C – 155°C
Boiling Point : 117°C to 118°C at 14 mmHg
Storage Temperature : 2-8°C inert atmosphere
LOD : NA
Solubility : Methanol and Chloroform
Density : 1.4283
Moisture content : 0.50 %
Description : It is a member of the phenylacetic acid family, with a nitro group at the para (4) position of the phenyl ring. The compound serves as an intermediate in the synthesis of various organic chemicals, including dyestuffs, pharmaceuticals, penicillin precursors, and local anesthetics.
Applications as a Building Block in Specialized Chemical Syntheses
The reactivity of 4-nitrophenylacetic acid allows its use as a foundational molecule in the synthesis of more complex structures with significant biological applications.
Development of Angiogenesis Inhibitors
This compound is utilized as an intermediate in the synthesis of compounds with potential anti-angiogenic properties. Angiogenesis, the formation of new blood vessels, is a critical process for tumor growth, and its inhibition is a key strategy in cancer therapy. Research has shown that this compound is a starting material for the synthesis of 5,7-dimethyl-2-aryl-3H-pyrrolizin-3-ones, a class of compounds investigated for their ability to act as angiogenesis inhibitors. In one synthetic pathway, this compound undergoes a base-catalyzed condensation with furfuraldehyde, which is then further modified to produce a series of analogues evaluated for antiangiogenic activity using methods like the chorioallantoic membrane (CAM) assay.
Synthesis of Fluorinated Compounds with Biological Relevance (e.g., in Drug Discovery)
The incorporation of fluorine into organic molecules is a common strategy in medicinal chemistry to enhance metabolic stability, binding affinity, and other pharmacokinetic properties. this compound and its derivatives serve as precursors for such fluorinated compounds. For instance, research has demonstrated a cobalt-catalyzed decarboxylative difluoroalkylation of nitrophenylacetic acid salts, providing a method to construct various difluoroalkylated products. This method can be applied to the late-stage functionalization of biologically relevant molecules.
Additionally, derivatives like 3-fluoro-4-nitro-phenylacetic acid are used to synthesize compounds where fluorine substitution significantly enhances biological potency. The synthesis of 2-Fluoroethyl 2-(4-nitrophenyl)acetate is another example, creating a fluoroorganic compound that serves as a building block for more complex molecules with potential pharmacological activities.
Role as a Precursor in Semi-Synthetic Antibiotic Production (e.g., for 6-Aminopenicillanic Acid)
The enzyme penicillin acylase (also known as penicillin amidohydrolase) is of major pharmaceutical importance as it catalyzes the hydrolysis of penicillin G to yield phenylacetic acid and 6-aminopenicillanic acid (6-APA). 6-APA is the essential precursor for the industrial production of a wide range of semi-synthetic penicillin antibiotics.
While not a direct precursor in the same way as penicillin G, this compound is a crucial research compound in this field. As a derivative of phenylacetic acid, it is used extensively in studies of penicillin acylase to understand its structure, specificity, and catalytic mechanism. By studying how inhibitors and alternative substrates like this compound bind to the enzyme, researchers can gain insights that facilitate the engineering of more efficient enzymes, ultimately optimizing the production of 6-APA and semi-synthetic antibiotics.
Biochemical and Enzymatic Interaction Studies
The chemical properties of this compound make it a suitable ligand for investigating the mechanisms and structures of various enzymes.
Investigations into Enzyme Inhibition Mechanisms (e.g., Malonic Enzyme/3-Hydroxyacyl-CoA Dehydrogenase)
This compound has been identified as an inhibitor of specific enzymes. It has been shown to inhibit malonic enzyme, which is also known as 3-hydroxyacyl-CoA dehydrogenase. The proposed mechanism for this inhibition involves the nitro group on the compound molecule, which is thought to react with a cysteine residue located in the active site of the enzyme. Esters of this compound, such as 4-nitrophenylacetate, have also been employed as substrates in assays for other enzymes, including monoglyceride lipase (B570770) (MGL), allowing for the screening and characterization of novel enzyme inhibitors.
Ligand-Enzyme Binding Studies with Penicillin Acylase via X-ray Crystallography
Detailed structural insights into ligand-enzyme interactions have been obtained by studying this compound with penicillin acylase. X-ray crystallography has been used to determine the structure of penicillin acylase in complex with various phenylacetic acid derivatives, including this compound, to elucidate the principles of substrate and inhibitor binding.
These studies reveal that this compound acts as a competitive inhibitor of penicillin acylase. The crystallographic data show that upon binding, the ligand can induce conformational changes within the enzyme’s active site. Specifically, certain amino acid residues in the binding pocket can shift to accommodate different ligands. In the complex with this compound, the carboxylic acid group of the ligand is shifted out of the binding pocket toward the solvent when compared to other ligands. This structural information provides a clear rationale for the observed kinetic results and contributes to a deeper understanding of the enzyme’s mechanism, which is valuable for potential protein engineering applications.
4-Nitrophenylacetic acid is primarily used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It serves as a building block in organic chemistry for creating various compounds, including angiogenesis inhibitors, squaraine dyes, and precursors for penicillin and local anesthetics. It can also function as a catalyst and a pH indicator.
Applications in synthesis and processing
- Pharmaceuticals: Acts as an intermediate for synthesizing Active Pharmaceutical Ingredients (APIs). It is also used in the preparation of precursors for penicillin and local anesthetics.
- Agrochemicals: Used as a building block in the synthesis of agrochemical compounds.
- Specialty chemicals: Involved in the synthesis of dyes, such as amino-substituted squaraine dyes, and complex molecules like 5,7-dimethyl-2-aryl-3H-pyrrolizin-3-ones, which may act as angiogenesis inhibitors.
- Catalysis: Functions as a catalyst to facilitate various chemical reactions in pharmaceutical production.
Other applications
- pH indicator: Due to its acidic nature, it can be used as a pH indicator in biochemical assays.
- Biochemical assays: Employed as a substrate or reagent in certain biochemical assays.
Pharmaceutical industry
- API Intermediate: Serves as a building block for manufacturing active pharmaceutical ingredients (APIs).
- Precursors: Used in the synthesis of penicillin precursors and local anesthetics.
- Active Esters: A reagent for preparing activated 4-nitrophenyl esters of N-protected amino acids, which are used in peptide synthesis.
Dyes and pigments
- Intermediate: A precursor for the synthesis of various dyestuffs.
- Dye Synthesis: Can be used in the one-step construction of amino-substituted squaraine dyes.
Other chemical synthesis
- Angiogenesis Inhibitors: Used to synthesize compounds like 5,7-dimethyl-2-aryl-3H-pyrrolizin-3-ones, which may act as angiogenesis inhibitors.
- Catalyst: Acts as a catalyst to facilitate chemical reactions in pharmaceutical formulations.
