439858-40-9

Basic information

• Product Name: 1-ACETOXY-3-(ACETOXYMETHOXY)CARBONYL-2,2,5,5-TETRAMETHYLPYRROLIDINE
• Synonyms: DACPY;1-ACETOXY-3-(ACETOXYMETHOXY)CARBONYL-2,2,5,5-TETRAMETHYLPYRROLIDINE;1-(Acetyloxy)-2,2,5,5-tetraMethyl-3-pyrrolidinecarboxylic Acid (Acetyloxy)Methyl Ester
• CAS NO: 439858-40-9
• Molecular Formula: C14H23NO6
• Molecular Weight: 301.34
• Product Categories: Spin Labeling Compounds;Heterocycles
• Mol File: 439858-40-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 358.2°C at 760 mmHg
• Flash Point: 170.4°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 2.6E-05mmHg at 25°C
• Refractive Index: 1.486
• CAS DataBase Reference: 1-ACETOXY-3-(ACETOXYMETHOXY)CARBONYL-2,2,5,5-TETRAMETHYLPYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ACETOXY-3-(ACETOXYMETHOXY)CARBONYL-2,2,5,5-TETRAMETHYLPYRROLIDINE(439858-40-9)
• EPA Substance Registry System: 1-ACETOXY-3-(ACETOXYMETHOXY)CARBONYL-2,2,5,5-TETRAMETHYLPYRROLIDINE(439858-40-9)

Safety Data

• Hazardous Substances Data: 439858-40-9(Hazardous Substances Data)

Usage

Description

1-ACETOXY-3-(ACETOXYMETHOXY)CARBONYL-2,2,5,5-TETRAMETHYLPYRROLIDINE is an acyl-protected hydroxylamine compound that serves as a spin label generator for specialized applications in brain imaging.

Uses

Used in Medical Imaging Industry:
1-ACETOXY-3-(ACETOXYMETHOXY)CARBONYL-2,2,5,5-TETRAMETHYLPYRROLIDINE is used as a spin label generator for Electron Paramagnetic Resonance (EPR) brain imaging. It plays a crucial role in enhancing the visualization and understanding of brain structures and functions, aiding researchers and medical professionals in diagnosing and monitoring various neurological conditions.

InChI:InChI=1/C14H23NO6/c1-9(16)19-8-20-12(18)11-7-13(3,4)15(14(11,5)6)21-10(2)17/h11H,7-8H2,1-6H3

Upstream product

• 96623-58-4 1-hydroxy-3-carboxy-2,2,5,5-tetramethylpyrrolidine 
• 590-97-6 acetoxymethyl bromide 

Relevant articles and documents

Acyl-protected hydroxylamines as spin label generators for EPR brain imaging

In a search for novel electron paramagnetic resonance (EPR) brain imaging agents, we have designed and synthesized the acyl-protected hydroxylamines 1-acetoxy-4-methoxycarbonyl-2,2,6,6-tetramethylpiperidine (AMCPe), 1-acetoxy-3-methoxycarbonyl-2,2,5,5-tetramethylpyrrolidine (AMCPy), and 1-acetoxy-3-(acetoxymethoxy)carbonyl-2,2,5,5-tetramethylpyrrolidine (DACPy), in which both the ring size and the number of ester functions were varied. In all of them, the nitroxide was first reduced and the resultant hydroxylamine was then protected with an acetyl group. These compounds are lipophilic, which is a major prerequisite for blood-brain barrier penetration. Once in the brain, esterases and oxidants quickly convert these derivatives into ionic, water-soluble radicals and thus EPR detectable species that then reside in the central nervous system for periods of time sufficient for detection and imaging. The biological relevancy of these new compounds in mice has been assessed, and their biodistribution patterns have been compared. The five-membered ring derivative AMCPy emerged as a potent EPR brain imaging agent while the other two derivatives, AMCPe and DACPy, were quite ineffective.