2154-68-9

Usage

Uses

Used in Chemistry and Research:
3-Carboxy-PROXYL is used as a reagent for the synthesis and reactions of stable nitroxyl radicals. Its application in this field is crucial for the development of new compounds and materials with potential applications in various industries.
Used in Pharmaceutical and Biological Studies:
3-Carboxy-PROXYL is used as a tool to study molecular migration and the long-term stability of seeds and pollen. This helps researchers understand the mechanisms behind seed and pollen viability, which is essential for agriculture and plant breeding.
Used in Material Science:
3-Carboxy-PROXYL is used in the preparation of a tetraphenylporphyrin bearing a nitroxyl radical. 3-CARBOXY-PROXYL has potential applications in the development of advanced materials with unique optical, electronic, and magnetic properties.
Used in Analytical Chemistry:
3-Carboxy-PROXYL has been used to determine distribution coefficients of neutral solubilizates in anionic micelles. This application is vital for understanding the behavior of solubilizates in various environments, which can be useful in the development of new drugs and chemical products.

InChI:InChI=1/C9H17NO3/c1-8(2)5-6(7(11)12)9(3,4)10(8)13/h6,13H,5H2,1-4H3,(H,11,12)/p-1/t6-/m1/s1

Upstream product

• 81635-38-3 3-bromo-2,2,6,6-tetramethyl-1-oxyl-piperidine-4-one 
• 46247-54-5 3‐methoxycarbonyl‐2,2,5,5‐tetramethyl‐pyrrolidine‐1‐oxyl 
• 96623-58-4 1-hydroxy-3-carboxy-2,2,5,5-tetramethylpyrrolidine 

Downstream Products

• 56948-70-0 cortisol 21-(2,2,5,5-tetramethylpyrrolidin-1-yloxy)-3-carboxylate 
• 56948-71-1 testosterone 17-(2,2,5,5-tetramethylpyrrolidin-1-yloxyl)-3-carboxylate 
• 27298-75-5 3-(hydroxymethyl)-2,2,5,5-tetramethylpyrrolidinyl-1-oxy 
• 61593-19-9 3-chloroformyl-2,2,5,5-tetramethylpyrrolidine-1-oxyl 
• 96623-58-4 1-hydroxy-3-carboxy-2,2,5,5-tetramethylpyrrolidine 
• 1227476-15-4 Azobenzene 
• 21913-97-3 3-carboxyl-PROXYL p-nitrophenyl ester 
• 439858-38-5 AMCPy 
• 106905-00-4 iron(III) 5,10,15,20-tetra-p-tolylporphyrin 2,2,5,5-tetramethyl-1-oxypyrrolidine-3-carboxylate 
• 1253509-58-8 C₅₅H₈₆NO₁₀ 
• 1253509-61-3 C₆₄H₁₀₀N₂O₁₂ 
• 1391158-78-3 C₂₇H₃₄NO₇ 
• 1425495-88-0 3'-N-(1-oxyl-2,2,5,5-tetramethyl-3-pyrrolidinylcarbonyl)-amido-AVE8063 
• 1599434-86-2 C₁₃H₂₀NO₅ 

Relevant academic research and scientific papers

A Study of the Favorskii Rearrangement with 3-Bromo-4-oxo-2,2,6,6-tetramethylpiperidin-1-oxyl

Favorskii rearrangement reactions of the title compound with sodium hydroxide, sodium ethoxide, ammonia, several aliphatic amines, and ethyl sodiomalonate resulting in pyrrolidine nitroxyl radicals are described.

A cyanine dye based supramolecular photosensitizer enabling visible-light-driven organic reaction in water

We report the aggregation-induced photosensitizing activity of a cyanine dye in water and the mechanism. In addition, using the supramolecular assembly, visible-light-driven photooxidation of hydrophobic aromatic compounds in water was successfully performed. This journal is

EPR detection of cellular and mitochondrial superoxide using cyclic hydroxylamines

Superoxide (O2) has been implicated in the pathogenesis of many human diseases, but detection of the O2 radicals in biological systems is limited due to inefficiency of O2 spin trapping and lack of site-specific information. This work studied production of extracellular, intracellular and mitochondrial O2 in neutrophils, cultured endothelial cells and isolated mitochondria using a new set of cationic, anionic and neutral hydroxylamine spin probes with various lipophilicity and cell permeability. Cyclic hydroxylamines rapidly react with O2, producing stable nitroxides and allowing site-specific O2 detection in intracellular, extracellular and mitochondrial compartments. Negatively charged 1-hydroxy-4-phosphono-oxy-2,2,6,6-tetramethylpiperidine (PP-H) and positively charged 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl-trimethylammonium (CAT1-H) detected only extramitochondrial O2. Inhibition of EPR signal by SOD2 over-expression showed that mitochondria targeted mitoTEMPO-H detected intramitochondrial O2 both in isolated mitochondria and intact cells. Both 1-hydroxy-3-carboxy-2,2,5,5-tetramethylpyrrolidine (CP-H) and 1-hydroxy-3-methoxycarbonyl-2,2,5,5-tetramethylpyrrolidine (CM-H) detected an increase in cytoplasm O2 stimulated by PMA, but only CM-H and mitoTEMPO-H showed an increase in rotenone-induced mitochondrial O2. These data show that a new set of hydroxylamine spin probes provide unique information about site-specific production of the O2 radical in extracellular or intracellular compartments, cytoplasm or mitochondria.

Facile synthesis of 3-methoxycarbonyl-2,2,5,5-tetra-methylpyrrolidine-1-oxyl and derivatives

We have achieved an efficient alternative synthesis of blood-brain-barrier permeable nitroxyl radicals 3-methoxycarbonyl-2,2,5,5-tetra-methylpyrrolidine-1-oxyl (1a) and 3-ethoxycarbonyl-2,2,5,5-tetramethylpyrroli-dine-1-oxyl (1b), which affords 1a and 1b in 65% isolated yields by four steps from 2,2,6.6-tetramethyl-4-piperidone (2), respectively. This protocol is applicable to the synthesis of 3-isopropoxy-2,2,5,5-tetramethylpyrrolidine-1-oxyl (1c) and 3-carbonyl-2,2,5,5-tetramethylpyrro-lidine-1-oxyl (6).