33490-11-8

Basic information

• Product Name: 4-OXO-2,2,6,6-TETRAMETHYLPIPERIDINE-1-15N-1-OXYL
• Synonyms: 4-OXO-2,2,6,6-TETRAMETHYLPIPERIDINE-1-15N-1-OXYL;4-Oxo-TEMPO-1-15N
• CAS NO: 33490-11-8
• Molecular Formula: C9H16NO2 *
• Molecular Weight: 171.24
• EINECS: 220-778-7
• Mol File: 33490-11-8.mol

Chemical Properties

• Melting Point: 35 °C(lit.)
• Appearance: /
• CAS DataBase Reference: 4-OXO-2,2,6,6-TETRAMETHYLPIPERIDINE-1-15N-1-OXYL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-OXO-2,2,6,6-TETRAMETHYLPIPERIDINE-1-15N-1-OXYL(33490-11-8)
• EPA Substance Registry System: 4-OXO-2,2,6,6-TETRAMETHYLPIPERIDINE-1-15N-1-OXYL(33490-11-8)

Safety Data

• Hazardous Substances Data: 33490-11-8(Hazardous Substances Data)

Upstream product

• 137003-52-2 <15N>-2,2,6,6-tetramethyl-4-piperidone 

Downstream Products

• 12169-67-4 cyclohexa-1->5-dienyl 
• 122133-94-2 ⁽¹⁵⁾N-labeled 2,2,6,6-tetramethylpiperid-4-one-1-hydroxyl 
• 79494-16-9 [15N]-4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl 

Relevant articles and documents

Synthesis of nitroxyl radicals for overhauser-enhanced magnetic resonance imaging

Non-invasive measurement and visualization of free radicals in vivo would be important to clarify their roles in the pathogenesis of free radical-associated diseases. Nitroxyl radicals can react with free radicals and be derivatized to achieve specific cellular / subcellular localizing capabilities while retaining the simple spectral features useful in imaging. Overhauser-enhanced magnetic resonance imaging (OMRI), which is a double resonance technique, creates images of free radical distributions in small animals by enhancing the water proton signal intensity via the Overhauser Effect. In this study, we synthesized various nitroxyl probes having 15N nuclei and deuterium, and measured the enhancement factor for Overhauser-enhanced magnetic resonance imaging experiments. 15N-D-4- Oxo-2,2,6,6-tetramethylpiperidine-1-oxyl (15N-D-oxo-TEMPO) has the highest enhancement factor compared with other nitroxyl probes. The proton signal enhancement was higher for 15N-labeled nitroxyl probes when compared to the 14N-labeled analogues because of the reduced spectral multiplicity of the I = 1/2 nucleus. Furthermore, this enhancement is proportional to the line width and number of electron spin resonance lines of nitroxyl radicals. Finally, we compared the Overhauser-enhanced magnetic resonance image of 15N-labeled, deuterated 4-Oxo-2,2,6,6- tetramethylpiperidine-1-oxyl with that of 14N-H-TEMPOL. These results suggested that the selective deuteration of the nitroxyl probes enhanced the signal-to-noise ratio and thereby improved spatial and temporal resolutions.

Time resolved CW-EPR spectroscopy of powdered samples: Electron spin polarization of a nitroxyl radical adsorbed on NaY zeolite, generated by the quenching of excited triplet ketones

Chemically induced dynamic electron polarization (CIDEP) generated in a faujasite zeolite (NAY) by the interaction between a stable free radical (4-oxo-TEMPO) and the triplet state of benzophenone was investigated by time-resolved electron spin resonance spectroscopy (TR-CW-EPR). The TR-CW-EPRs were performed by either pulling a long tube containing powdered zeolite through the EPR cavity during the laser irradiation, or by flowing a liquid transport medium (polydimethylsiloxane) for the zeolite powder, through a flat cell in the EPR cavity. CIDEP was observed for intermolecular triplet quenching (benzophenone triplets with 4-oxo-TEMPO) and intramolecular triplet quenching using a covalently linked TEMPO-benzophenone molecule. The identification of the polarized nitroxide structure was confirmed by employing both 14N and 15N 4-oxo-TEMPO isotopomers. The kinetics of the triplet quenching inside the zeolite were studied by diffuse reflection laser flash photolysis.

The synthesis of EPR differentiable spinlabels and their coupling to uridine

For EPR measurements of RNA, DNA, or proteins, the occurrence of the paramagnetic species is necessary. The aim of this work is to improve the synthesis of two different EPR spinlabels 2,2,6,6-tetra methyl-3,4-dehydro- piperidin-N-oxyl-4-acetylene (TEMPA) 6 and 15N-labeled TEMPA 6* and their coupling to uridine. The yield of the synthesis of TEMPA could be increased to 40% and the second nitroxide 2,2,6,6-tetramethyl-3,4-dehydro-piperidin-15N-oxyl- 4-acetylene 6* could be synthesized with a yield of 11%. Copyright Taylor & Francis Group, LLC.

A time-resolved electron paramagnetic resonance investigation of the spin exchange and chemical interactions of reactive free radicals with isotopically symmetric (14N-X-14N) and isotopically asymmetric ( 14N-X-15

Interactions between reactive free radicals (r) with stable mononitroxyl radicals (N) and bisnitroxyl radicals (N-X-N) were studied by time-resolved electron paramagnetic resonance (TR-EPR). Reactive spin-polarized free radicals (r#), with non-