55482-03-6

Basic information

• Product Name: 2,2-dimethyl-5-hydroxy-1-pyrrolidinyloxy
• Synonyms: 2,2-dimethyl-5-hydroxy-1-pyrrolidinyloxy
• CAS NO: 55482-03-6
• Molecular Formula: C₆H₁₂NO₂
• Molecular Weight: 0
• Mol File: 55482-03-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,2-dimethyl-5-hydroxy-1-pyrrolidinyloxy(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-dimethyl-5-hydroxy-1-pyrrolidinyloxy(55482-03-6)
• EPA Substance Registry System: 2,2-dimethyl-5-hydroxy-1-pyrrolidinyloxy(55482-03-6)

Safety Data

• Hazardous Substances Data: 55482-03-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H12NO2/c1-6(2)4-3-5(8)7(6)9/h5,8H,3-4H2,1-2H3

Upstream product

• 3317-61-1 5,5-Dimethyl-1-pyrroline N-oxide 
• 67-56-1 methanol 
• 96-26-4 dihydroxyacetone 
• 64-17-5 ethanol 
• 109-73-9 N-butylamine 
• 98-86-2 acetophenone 
• 141-53-7 sodium formate 
• 56-82-6 Glyceraldehyde 
• 141-46-8 Glycolaldehyde 

Relevant articles and documents

Kinetics of spin trapping superoxide, hydroxyl, and aliphatic radicals by cyclic nitrones

Spin trapping coupled with electron paramagnetic resonance (EPR) spectroscopy has surfaced as one of the most specific and reliable methods for identifying free radicals in biological systems. Despite extensive studies focused on the kinetics of radical trapping by cyclic nitrones, the mechanism has not been fully elucidated. Moreover, major controversies still persist even regarding the efficiency and the rate constants of the trapping reaction. The present research used pulse radiolysis for studying the reaction of 5,5-dimethyl-1-pyrroline N-oxide 1 (DMPO) and of the ester-containing derivative, 5-tert-butoxycarbonyl-5-methyl-1-pyrroline N-oxide 4, with OH, O2-, CO2 -, C(OH)(CH3)2, CH2OH, and CH3. The results reveal that radical trapping is far more complex then previously realized. Radiation chemical experiments combined with EPR demonstrate that about 30% of OH add to nitrones 1 and 4 at position 2, yielding the corresponding persistent aminoxyls. The remaining OH radicals form transient intermediates that rapidly decay bimolecularly. These transient intermediates react with oxygen with rate constants that are significantly lower than those generally reported for alkyl radicals, which suggests that they are not simple carbon-centered radicals generated as a result of H-abstraction from the methyl or methylene groups of the nitrones. It is also shown that the addition of O2- and various aliphatic radicals to the nitrones is an equilibrium process. The upper limit for the rate constant of the reaction of nitrone 4 with O2 - was 3 M-1 s-1. The rate constant for the reaction of nitrone 1 with O2- was determined to be 170 ± 40 M-1 s-1. This value is significantly higher than those previously determined by following the formation of the corresponding aminoxyl by EPR, which indicates that the yield of the aminoxyl is only a small fraction of the reacting O2-.

Guest inclusion in cucurbiturils studied by ESR and DFT: The case of nitroxide radicals and spin adducts of DMPO and MNP

We present an ESR and DFT study of the interaction of cucurbiturils CB[6], CB[7], and CB[8] with ditert- butyl nitroxide ((CH3) 3C)2NO (DTBN) and with spin adducts of 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) and 2- methyl-2-nitrosopropane (MNP). The primary goal was to understand the structural parameters that determine the inclusion mechanism in the CBs using DTBN, a nitroxide with great sensitivity to the local environment. In addition, we focused on the interactions with CBs of the spin adducts DMPO/OH and MNP/CH2COOH generated in aqueous CH3COOH. A range of interactions between DTBN and CBs was identified for pH 3.2, 7, and 10. No complexation of DTBN with CB[6] was deduced in this pH range. The interaction between DTBN and CB[7] is evident at all pH values: in and out nitroxides, with 14N hyperfine splitting, aN, values of 15.5 and 17.1 G, respectively, were detected by ESR. Interaction of DTBN with CB[8] was also detected for all pH values, and the only species had aN = 16.4 G, a result that can be rationalized by an in nitroxide in a less hydrophobic environment compared to CB[7]. Computational studies indicated that the DTBN complex with CB[7] is thermodynamically favored compared to that in CB[8]; the orientations of the NO group are parallel to the CB[7] plane and perpendicular to the CB[8] plane (pointing toward the annulus). Addition of sodium ions led to the ESR detection of a three-component complex between CB[7], DTBN, and the cations; the ternary complex was not detected for CB[8]. The DMPO/OH spin adduct was stabilized in the presence of CB[7], but the effect on aN was negligible, indicating that the N-O group is located outside the CB cavity. Computational studies indicated more favorable energetics of complexation for DMPO/OH in CB[7] compared to DTBN. An increase of aN was detected in the presence of CB[7] for the MNP/CH2COOH adduct generated in CH3COOH, a result that was assigned to the generation of the three-component radical between the spin adduct, sodium cations, and CB[7].

THE PRODUCTION OF FREE RADICALS DURING THE AUTOXIDATION OF MONOSACCHARIDES BY BUFFER IONS

The production of free radicals during the autoxidation of simple monosaccharides at 37 degree has been studied by the elctron spin resonance (e. s. r.) technique of spin trapping.In the presence of the spin trap 5,5-dimethyl-1-pyrroline N-oxide (DMPO), monosaccharides undergoing autoxidation produced hydroxyl and 1-hydroxyalkyl radical-derived spin adducts, indicating that hydroxyl and hydroxyalkyl free-radicals are involved in the autoxidation of monosaccharides.The pH profile for the production of free radicals from monosaccharides undergoing autoxidation revealed the formation of both hydroxyl and hydroxyalkyl radicals at relatively high pH, whereas at low pH, only the formation of hydroxyalkyl radicals was observed; the transition between these routes for the production of free radicals occurred at pH 8.0 - 8.5.Glycolaldehyde, glyceraldehyde, dihydroxyacetone, and erythrose are relatively rapidly enolised (to an ene-diol) and autoxidised with the concomitant production of free radicals.Ribose and glucose enolise and autoxidise very slowly without detectable production of free radicals.A comparison of the pH profiles of the rates of enolisation and the pH dependence of the production of free radicals from glyceraldehyde during autoxidation suggests that a change in reaction mechanism occurs at pH 8.2.Below pH 8.2, the rates of enolisation and autoxidaiton increase with increasing pH, with a concomitant increase in the formation of hydroxyalkyl spin-adducts.Above pH 8.2, glyceraldehyde undergoing autoxidation shows a much higher rate of enolisation than of autoxidation and, although the formation of hydroxyalkyl radicals is decreased, the production of hydroxyl radicals is also obsserved.A free-radical mechanism for the autoxidation of monosaccharides is proposed, to account for the pH-dependent characteristics of the production of free radicals and the relationships between the production of free radicals, autoxidation, and enolisation of the monosaccharides.

6-Methyl 3-chromonyl 2,4-thiazolidinedione/2,4-imidazolidinedione/2-thioxo- imidazolidine-4-one compounds: Novel scavengers of reactive oxygen species

The benefits of antioxidants on human health are usually ascribed to their potential ability to remove reactive oxygen species providing protection against oxidative stress. In this paper the free radicals scavenging activities of nine 6-methyl 3-chromonyl derivatives (CMs) were evaluated for the first time by the chemiluminescence, electron paramagnetic resonance, spin trapping and 2,2-diphenyl-1-picrylhydrazyl (DPPH?) methods. The total antioxidant capacity was also measured using a ferric-ferrozine reagent. Compounds having a hydrogen atom at the N3-position of the β-ring were effective in quenching CL resulted from the KO2/18-crown-6-ether system (a source of superoxide anion radical, O2??) in a dose-dependent manner over the range of 0.05-1 mmol/L [IC50 ranged from 0.353 (0.04) to 0.668 (0.05) mmol/L]. The examined compounds exhibited a significant scavenging effect towards hydroxyl radicals (HO? HO?), produced by the Fenton reaction, and this ranged from 24.0% to 61.0%, at the concentration of 2.5 mmol/L. Furthermore, the compounds examined were also found to inhibit DPPH? and this ranged from 51.9% to 97.4% at the same concentration. In addition, the use of the total antioxidant capacity assay confirmed that CM compounds are able to act as reductants. According to the present study, CM compounds showed effective in vitro free radical scavenging activity and may be considered as potential therapeutics to control diseases of oxidative stress-related etiology. Copyright 2013 John Wiley & Sons, Ltd. Copyright

Probing the surface of transition-metal nanocrystals by chemiluminesence

We propose a simple chemiluminescence (CL) method for investigation of the surface of Co-based nanocrystals (NCs). Using a combination of CL and spin-trap electron paramagnetic resonance techniques, we systematically studied the generation of reactive oxygen species (ROS) at the surface of differently sized CoPt3 spherical NCs and CoPt3/Au nanodumbbells. We have shown that differently sized CoPt3 NCs can promote the formation of ROS and as a result can lead to the oxidation of luminol accompanied by the emission of the light. CL allows monitoring the stability of transition-metal-based NCs against oxidation and dissolution. We found by CL that cobalt ions slowly leach from the surface of CoPt3 NCs even under very mild conditions; however, the amount of the leached cobalt ions does not exceed the maximal concentration of cobalt at the NC surface indicating that only surface atoms can go into solution.

Dentin is dissolved by high concentrations of L-ascorbic acid 2-[3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl) -2H-1-benzopyran-6-yl-hydrogen phosphate] potassium salt with or without hydrogen peroxide

L-Ascorbic acid 2-[3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12- trimethyltridecyl)-2H-1-benzopyran-6-yl-hydrogen phosphate] potassium salt (EPC-K1) is a conjugate of vitamin C and vitamin E that is water-soluble and stable at room temperature. EPC-K1 has been developed as a hydroxyl radical (·OH) scavenger and antioxidant. In a previous tooth whitening experiment, it was accidentally found that tooth (dentin) blocks were dissolved by EPC-K1 with H2O 2. In the current study, high concentrations of EPC-K1 (2.5, 25mM) with 3% H2O2 dissolved and caused the collapse of dentin blocks. Similar concentrations of EPC-K1 without 3% H 2O2, however, dissolved the dentin blocks without collapse over a 3-week period. In these cases, a ·OH-like signal was detected using an ESR spin-trapping method. The volume of calcium in solution (including the dentin block) increased on the addition of EPC-K1 in a concentration-dependent manner. In addition, the calcium : phosphorus ratio changed from 2 : 1 in sound dentin to 1 : 2 in the collapsed dentin block. High concentrations of EPC-K1 are therefore considered to have calcium chelating and dentin dissolving activity. The dentin dissolving activity was enhanced when EPC-K1 was used with H2O2. EPC-K1 had no protective effect when used in tooth whitening with H2O2.

Sensitive determination of triacetone triperoxide explosives using electrogenerated chemiluminescence

Sensitive and selective detection and quantification of high explosive triacetone triperoxide (TATP) with electrogenerated chemiluminescence (ECL) at a glassy carbon electrode in water-acetonitrile solvent mixture were reported. In the presence of ruthenium(II) tris(bipyridine), TATP or hydrogen peroxide derived from TATP via UV irradiation or acid treatment produced ECL emissions upon cathodic potential scanning. Interference from hydrogen peroxide on TATP detection was eliminated by pretreatment of the analyte with catalase enzyme. Selective detection of TATP from hexamethylene triperoxide diamine (HMTD, another common peroxide-based explosive) was realized by comparing ECL responses obtained from the anodic and the cathodic potential scanning; TATP produced ECL upon cathodic potential scanning only, whereas HMTD produced ECL upon both cathodic and anodic potential scanning. The hydroxyl radical formed after the electrochemical reduction of TATP was believed to be the key intermediate for ECL production, and its stability was strongly dependent on the solution composition, which was verified with electron paramagnetic resonance spectroscopy. A detection limit of 2.5 μM TATP was obtained from direct electrochemical reduction of the explosive or hydrogen peroxide derived from TATP in 70/30% (v/v) water-acetonitrile solutions, which was ～400 times lower than that reported previously based on liquid chromatography separation and Fourier transform infrared detection.

Kinetic study and theoretical analysis of hydroxyl radical trapping and spin adduct decay of alkoxycarbonyl and dialkoxyphosphoryl nitrones in aqueous media

Spin-trap development is important because of limitations that still exist among the currently used nitrone spin traps. This study correlates the experimental kinetic data with theoretical calculations, a novel approach that could be helpful in the future design of new spin traps. The kinetics of hydroxyl radical (.OH) trapping and spin adduct decay of the alkoxycarbonyl-nitrones 5-ethoxycarbonyl-5-methyl-l-pyrroline N-oxide (EMPO) and 5-butoxycarbonyl-5-methyl-l-pyrroline N-oxide (BocMPO) as well as the dialkoxyphosphoryl-nitrones 5-diethoxyphosphoryl-5-methyl-l-pyrroline N-oxide (DEPMPO) and 5-diisopropyloxyphosphoryl-5-methyl-1-pyrroline N-oxide (DIPPMPO) have been investigated and compared with those of unsubstituted 5,5-dimethyl-1-pyrroline N-oxide (DMPO). Kinetic investigation was performed by the steady-state generation of .OH from H2O2 by UV photolysis in the presence of a nitrone. Apparent rate constants of .OH trapping by EMPO, BocMPO, DEPMPO, and DIPPMPO in competition with ethanol are all comparable, with kapp values ranging from 4.99 ± 0.36 to 4.48 ± 0.32 M-1 s-1 and the commonly used spin trap 5,5-dimethyl-l-pyrroline N-oxide (DMPO) having a lower kapp of 1.93 ± 0.05 M-1 s-1. Half-lives of the .OH adducts of EMPO, DEPMPO, and DIPPMPO are much longer (t1/2 = 127-158 min) than those of DMPO and BocMPO with half-lives of only 55 and 37 min, respectively. Geometry optimizations, frequency analyses, and single-point energies of the nitrones and their corresponding spin adducts were determined at the B3LYP/6-31G*//HF/6-31G* level to rationalize the experimental results.

Enhanced peroxidase-like activity of porphyrin functionalized ZnFe2O4 hollow nanospheres for rapid detection of H2O2 and glucose

Using a simple one-pot solvothermal method, binary metal oxide, magnetic and hollow ZnFe2O4 nanospheres functionalized with 5,10,15,20-tetrakis(4-carboxylphenyl)-porphyrin (Por-ZnFe2O4 HSs) were prepared and subsequently applied as a substitute for natural peroxidase. The Por-ZnFe2O4 HSs were characterized using powder X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM) and X-ray photoelectron spectroscopy (XPS). In comparison with bare ZnFe2O4 HSs, Por-ZnFe2O4 HSs exhibit enhanced intrinsic peroxidase-like activity. They demonstrate a fast colorimetric response to H2O2 with a detection limit as low as 0.86 μM. The catalytic mechanism of the system was proved to be a hydroxyl radical mechanism using electron spin resonance (ESR). By combining the Por-ZnFe2O4 HSs-catalyzed reaction and the enzymatic oxidation of glucose with glucose oxidase, a colorimetric platform for glucose detection was established. The Por-ZnFe2O4 HSs/glucose oxidase (GOx)/TMB system shows a good response toward glucose with a detection limit of 5.5 μM. Therefore, such nanocomposites have promising applications in biomimetic catalysis and environmental monitoring.

Antioxidative potential of fluvastatin via the inhibition of Nicotinamide Adenine Dinucleotide Phosphate (NADPH) oxidase activity

We previously reported that fluvastatin, a potent 3-hydroxy-3- methylglutaryl coenzyme A (HMG-CoA) reductase inhibitor, a strong lipid lowering drug, exerted an anti-atherosclerotic effect at doses insufficient to lower serum lipids in cholesterol fed rabbits. The evidence demonstrated that the superoxide allions from nicotinamide adenine dinucleotide phosphate (NADPH) oxidase plays a critical role in several steps in the development of atherosclerosis. This study was designed to determine the effects of HMG-CoA reductase inhibitors on the production of the superoxide anions of NADPH oxidase in isolated rat peritoneal neutrophils. Fluvastatin (1-10 μM) decreased phorbol 12-myristate 13-acetate (PMA, 10 nM)-dependent reactive oxygen species (ROS) generation in a concentration-dependent manner. It also (10 μM) decreased PMA-dependent O2 consumption of the rat neutrophils. These effects were reversed by the addition of mevalonate, a metabolite in the HMG-CoA reductase pathway. Treatment with pravastatin did not show any significant changes. Fluvastatin (10 μM) decreased ROS, such as hydroxyl radicals and superoxide anions generated by the Fenton reaction, and by the xanthine-xanthine oxidase system. Rats were treated with either fluvastatin (5 mg/kg per day, p.o.) or pravastatin (5 mg/kg per day, p.o.) for 1 week. Treatment with fluvastatin decreased the PMA-dependent ROS generation. The fluvastatin induced effect on the PMA-dependent ROS generation was reversed by the combined administration with 40 mg/kg mevalonate per day. The antioxidative effect of fluvastatin was thought to have caused not only the scavenging action of the radicals but also to have inhibited ROS generation by inhibiting the NADPH oxidase activity. This antioxidative potential of fluvastatin via the inhibition of NADPH oxidase activity may be profitable in preventing atherosclerosis.