2922-40-9

Basic information

• Product Name: P-NITRO-DL-PHENYLALANINE
• Synonyms: 4-NITRO-L-PHENYLANINEHYDRATE;DL-4-NO2-Phe-OH;2-Amino-3-(4-nitro-phenyl)-propionic acid;rac-(R*)-2-Amino-3-(4-nitrophenyl)-propionic acid;rac-(R*)-α-Amino-4-nitrobenzenepropanoic acid;4-Nitro-DL-phenylalanine hydrate,99%;P-NITRO-DL-PHENYLALA;4-Nitro-DL-phenylalanine 98%
• CAS NO: 2922-40-9
• Molecular Formula: C₉H₁₀N₂O₄
• Molecular Weight: 210.19
• EINECS: 220-868-6
• Product Categories: Pharmaceutical Raw Materials;Amino Acids;Unusual Amino Acids;Phenylalanine Derivatives;Peptide Synthesis;Unnatural Amino Acid Derivatives
• Mol File: 2922-40-9.mol
• Article Data: 11

Chemical Properties

• Melting Point: 236-237 °C (dec.)(lit.)
• Boiling Point: 414.1 °C at 760 mmHg
• Flash Point: 204.2 °C
• Appearance: beige powder
• Density: 1.408 g/cm³
• Vapor Pressure: 1.34E-07mmHg at 25°C
• Refractive Index: 1.614
• Storage Temp.: Store at RT.
• PKA: 2.12±0.10(Predicted)
• CAS DataBase Reference: P-NITRO-DL-PHENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: P-NITRO-DL-PHENYLALANINE(2922-40-9)
• EPA Substance Registry System: P-NITRO-DL-PHENYLALANINE(2922-40-9)

Safety Data

• Hazard Codes: T,C,F
• Statements: 25-34-11
• Safety Statements: 45-36/37/39-26-16
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 2922-40-9(Hazardous Substances Data)

Usage

Description

P-NITRO-DL-PHENYLALANINE, also known as 4-Nitro-DL-phenylalanine, is a chemical compound with the chemical formula C9H10N2O4. It is a beige powder and is recognized for its role as a chromophore. P-NITRO-DL-PHENYLALANINE is significant in various applications due to its unique properties and reactivity.

Uses

Used in Chromatography and Spectroscopy:
P-NITRO-DL-PHENYLALANINE is used as a convenient UV tag for the determination of overall purity of b-turn mimetics. Its chromophoric properties make it an ideal candidate for identifying and quantifying specific compounds in complex mixtures, which is crucial in the fields of pharmaceuticals and biochemistry.
Used in Environmental Analysis:
P-NITRO-DL-PHENYLALANINE serves as an internal standard for the determination of β-N-methylamino-L-alanine (L-BMAA) in environmental aqueous samples using proton nuclear magnetic resonance (1H NMR) technique. This application is vital in environmental science and toxicology, as it helps in the accurate measurement and monitoring of potentially harmful substances in the environment.
Used in Pharmaceutical Research:
In the pharmaceutical industry, P-NITRO-DL-PHENYLALANINE is utilized as a building block for the synthesis of various drugs and drug candidates. Its unique chemical properties allow for the creation of novel compounds with potential therapeutic applications.
Used in Chemical Synthesis:
P-NITRO-DL-PHENYLALANINE is also employed as an intermediate in the synthesis of various organic compounds, including those with potential applications in materials science, agrochemicals, and other specialty chemical industries. Its versatility as a synthetic building block makes it a valuable asset in the development of new products and technologies.

InChI:InChI=1/C9H10N2O4/c10-8(9(12)13)5-6-1-3-7(4-2-6)11(14)15/h1-4,8H,5,10H2,(H,12,13)/t8-/m1/s1

Upstream product

• 6265-87-8 2-acetylamino-2-(4-nitrobenzyl)malonic acid diethyl ester 
• 6265-86-7 formylamino-(4-nitro-benzyl)-malonic acid diethyl ester 
• 150-30-1 Phenylalanine 
• 110270-80-9 (4-nitro-benzyl)-malonic acid 
• 63-91-2 L-phenylalanine 
• 69555-14-2 ethyl N-diphenylmethylene glycine 
• 100-14-1 4-nitrobenzyl chloride 
• 100-97-0 hexamethylenetetramine 
• 101468-97-7 N-benzoyl-(4'-nitro)phenylalanine 
• 7152-75-2 (Z)-2-phenyl-4-(4-nitrobenzylidene)-(4H)-1,3-oxazol-5-one 
• 669775-21-7 methyl (N-benzoyl)-4'-nitrophenylalaninate 
• 882-06-4 4-nitro-trans-cinnamic acid 
• 949-99-5 4-nitro-3-phenyl-L-alanine 
• 56613-61-7 (R)-4-nitro-phenylalanine 

Downstream Products

• 61777-05-7 4-(4-nitro-benzyl)-oxazolidine-2,5-dione 
• 60666-01-5 (RS)-N-phthaloyl-p-nitrophenylalanine 
• 6949-60-6 N-formyl-4-nitro-phenylalanine 
• 99984-07-3 N-dichloroacetyl-4-nitro-phenylalanine 
• 2922-41-0 (p-aminophenyl)alanine 
• 55895-91-5 ethyl 2-amino-3-(4-nitrophenyl) propanoate 
• 62561-97-1 N-acetyl-4-nitro-DL-phenylalanine 
• 857766-77-9 4-nitro-N-phenylcarbamoyl-phenylalanine 
• 82611-60-7 2-benzyloxycarbonylamino-3-(4-nitrophenyl)propionic acid 
• 85317-52-8 methyl 2-amino-3-(4-nitrophenyl)propionate 
• 15482-94-7 rac-3-(4-nitrophenyl)-2-hydroxypropionic acid 
• 86937-80-6 2-tert-butoxycarbonylamino-3-(4-nitro-phenyl)-propionic acid 
• 101468-97-7 N-benzoyl-(4'-nitro)phenylalanine 
• 82283-43-0 2-Chloromethyl-4-[1-(4-nitro-phenyl)-meth-(Z)-ylidene]-4H-oxazol-5-one 

Relevant articles and documents

Self-assembling behaviour of a modified aromatic amino acid in competitive medium

Aromatic amino acid, specifically phenylalanine (Phe), is one of the most studied building blocks in peptide synthesis due to its importance in biology. It is reported in the literature that Phe-containing peptides have a high tendency to form different self-assembled materials due to efficient aromatic-aromatic interactions. In this article, we have tuned the supramolecular interactions of phenylalanine by making it electron-deficient upon introduction of the nitro group in the ring. The presence of the nitro group has a profound influence on the self-assembly process. It has been observed that 4-nitrophenylalanine (4NP) is a highly efficient gelator compared with the native phenylalanine in DMSO solvent in terms of minimum gelation concentration and it forms hydrogen bonding mediated crystals in water. The change of self-assembling patterns of 4NP in these solvents was studied using X-ray diffraction, UV-Vis spectroscopy, FE-SEM and other techniques. With the help of different experimental data and density functional theory (DFT), we have simulated the theoretical structure of 4NP in DMSO. The theoretical structure of 4NP in DMSO is different compared with that of crystals in water. We then studied the self-assembly process of 4NP in the mixed solvent of DMSO (polar aprotic) and water (polar protic). Different competitive non-covalent interactions of solvents as well as the ratio of the solvent mixture guide the final self-assembly state of 4NP. This journal is

Nitration of Tyrosine in the Mucin Glycoprotein of Edible Bird's Nest Changes Its Color from White to Red

The edible bird's nest (EBN) of the swiftlet Aerodramus fuciphagus, a mucin glycoprotein, is usually white in color, but there also exist the more desirable red or "blood" EBN. The basis of the red color has been a puzzle for a long time. Here, we show that the nitration of the tyrosyl residue to the 3-nitrotyrosyl (3-NTyr) residue in the glycoprotein is the cause of the red color. Evidence for the 3-NTyr residue comes from (a) the quantitative analysis of 3-NTyr in EBN by enzyme-linked immunosorbent assay, (b) the ultraviolet-visible absorption spectra of red EBN as a function of pH being similar to 3-nitrotyrosine (3-NT), (c) the change in the color of red EBN from yellow at low pH to red at high pH just like 3-NT, and (d) strong Raman nitro bands at 1330 cm-1 (symmetric -NO2 stretch) and 825 cm-1 (-NO2 scissoring bend) for red EBN. The high concentrations of nitrite and nitrate in red EBN are also explained.

Immunomodulatory peptides

The invention relates to peptides derivatized with a hydrophilic polymer which, in some embodiments, bind to human FcRn and inhibit binding of the Fc portion of an IgG to an FcRn, thereby modulating serum IgG levels. The disclosed compositions and methods may be used in some embodiments, for example, in treating autoimmune diseases and inflammatory disorders. The invention also relates, in further embodiments, to methods of using and methods of making the peptides of the invention.