30310-80-6

Basic information

• Product Name: L-Proline, 4-hydroxy-1-nitroso-, (4R)- (9CI)
• Synonyms: L-Proline, 4-hydroxy-1-nitroso-, (4R)- (9CI);N-NITROSOHYDROXYPROLINE;NITROSOHYDROXYPROLINE;(4R)-1-Nitroso-4-hydroxy-L-proline;(4R)-4-Hydroxy-1-nitroso-L-proline;1-Nitroso-4β-hydroxy-L-proline;1-Nitroso-4β-hydroxypyrrolidine-2α-carboxylic acid;N-Nitroso-L-hydroxyproline
• CAS NO: 30310-80-6
• Molecular Formula: C₅H₈N₂O₄
• Molecular Weight: 160.12802
• Product Categories: PYRROLE;Heterocycles;Mutagenesis Research Chemicals;Nitric Oxide Reagents
• Mol File: 30310-80-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 129-131°C
• Boiling Point: 286°C (rough estimate)
• Flash Point: 245.7°C
• Appearance: /
• Density: 1.5101 (rough estimate)
• Vapor Pressure: 2.42E-11mmHg at 25°C
• Refractive Index: 1.4472 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Acetone (Slightly), DMSO (Slightly), Water (Slightly)
• PKA: 3.02±0.40(Predicted)
• CAS DataBase Reference: L-Proline, 4-hydroxy-1-nitroso-, (4R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: L-Proline, 4-hydroxy-1-nitroso-, (4R)- (9CI)(30310-80-6)
• EPA Substance Registry System: L-Proline, 4-hydroxy-1-nitroso-, (4R)- (9CI)(30310-80-6)

Safety Data

• Hazardous Substances Data: 30310-80-6(Hazardous Substances Data)

Usage

Description

L-Proline, 4-hydroxy-1-nitroso-, (4R)(9CI) is a derivative of the amino acid L-Proline, characterized by the presence of a nitroso group and a hydroxyl group. It is a tan solid with chemical properties that make it a potential compound of interest in various applications.

Uses

Used in Chemical Research:
L-Proline, 4-hydroxy-1-nitroso-, (4R)(9CI) is used as a research compound for studying the effects and interactions of nitroso derivatives in chemical and biological systems. Its unique structure allows scientists to explore its potential applications and properties in various fields.
Used in Food Industry (with caution):
L-Proline, 4-hydroxy-1-nitroso-, (4R)(9CI) is found in cured meat products as a result of the curing process. It is classified as a carcinogenic nitrosamine, which means that its presence in the food industry should be carefully monitored and controlled to ensure safety and minimize health risks for consumers.

InChI:InChI=1/C5H8N2O4/c8-3-1-4(5(9)10)7(2-3)6-11/h3-4,8H,1-2H2,(H,9,10)/t3-,4+/m1/s1

Upstream product

• 51-35-4 4R-4-hydroxyproline 

Downstream Products

• 51-35-4 4R-4-hydroxyproline 

Relevant articles and documents

(4R)-4-Hydroxy-1-nitroso-l-proline: synthesis, X-ray structure, ab initio and conformational calculations

4-Hydroxy-l-proline, an amino acid, an important component of collagen, was transformed into its N-nitroso-derivative, (4R)-4-hydroxy-1-nitroso-l-proline, 1 by butylnitrite in the acidic medium. The structure is a cyclic hydroxy-N-nitrosoacid with the carboxyl and hydroxyl groups trans to each other. The carboxyl group is in the syn-conformation. In the structure, the neutral molecules are connected via classical intermolecular O-H?O hydrogen bonds involving the hydroxyl and carboxyl groups [O?O=2.6251(14) ?], and form chains along the a-axis direction. The chains are linked into sheets via O-H?O hydrogen bond, [O?O=2.6813(15) ?] with participation of oxygen atom of nitroso group. Ab initio calculations based on density functional theory at the B3LYP/6-311++G(d, p) level of theory were performed to analyze the influence of 4-hydroxy-l-proline (Hyp) nitrosation on the conformation of the synthesized N-nitroso-compound. The geometry optimization of 1 and initial 4-hydroxy-l-proline was carried out in the gas phase and in solution using the polarizable continuum model. The single-point calculation was performed for the crystal structure of 1. The most stable conformer of 1 is observed in an aqueous solution. In this state, the pyrrolidine ring adopts an envelope conformation, which is also maintained in the gas phase. The twisted conformation of the pyrrolidine ring is present in all states of Hyp and in the crystal structure of 1. In 1 the interchange of five-membered ring conformation in solution and in the gas phase in comparison with the crystal is accompanied by an increase of the dipole moment of the molecule, which is maximal in solution.

Selective N-nitrosation of amines, N-alkylamides and N-alkylureas by N2O4 supported on cross-linked polyvinylpyrrolidone (PVP-N2O4)

N2O4 was supported on the cross-linked polyvinylpyrrolidone (PVP) to afford a solid, stable and recyclable nitrosating agent. This reagent shows excellent selectivity for N-nitrosation of dialkyl amines in the presence of diaryl-, arylalkyl-, trialkylamines and also for secondary amides in dichloromethane at room temperature under mild and heterogeneous conditions. Also N-nitroso-N-alkyl amides can be selectively prepared in the presence of primary amides and N-phenylamides under similar reaction conditions. Selective N-nitrosation or dealkylation and N-nitrosation of tertiary amines can also be performed by this reagent.

A new method for nitrosation of proline and related sec- -amino acids to N-nitrosamino acids with possible oncogenic activity.

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