157230-67-6

Basic information

• Product Name: DEPMPO
• Synonyms: DEPMPO;(2-METHYL-3,4-DIHYDRO-1-OXIDE-2H-PYRROL-2-YL)DIETHYLPHOSPHONATE;2-DIETHYLPHOSPHONO-2-METHYL-3,4-DIHYDRO-2H-PYRROLE 1-OXIDE;5-(DIETHYLPHOSPHONO)-5-METHYL-1-PYRROLINE N-OXIDE;5-(DIETHOXYPHOSPHONYL)-5-METHYL-1-PYRROLINE-N-OXIDE;5-(DIETHOXYPHOSPHORYL)-5-METHYL-1-PYRROLINE-N-OXIDE;5-(Diethoxyphosphoryl)-;P-(3,4-Dihydro-2-Methyl-1-oxido-2H-pyrrol-2-yl)phosphonic Acid Diethyl Ester
• CAS NO: 157230-67-6
• Molecular Formula: C9H18NO4P
• Molecular Weight: 235.22
• Product Categories: Spin Labeling Compounds;Analytical Chemistry;ESR Spectrometry;Spin Trapping Reagents
• Mol File: 157230-67-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 412.4°Cat760mmHg
• Flash Point: 203.2°C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 1.24E-06mmHg at 25°C
• Refractive Index: 1.469
• Storage Temp.: Freezer
• Solubility: Soluble in Water or Ethanol.
• PKA: 1.74±0.40(Predicted)
• Stability: Hygroscopic Oil, Light Sensitive
• CAS DataBase Reference: DEPMPO(CAS DataBase Reference)
• NIST Chemistry Reference: DEPMPO(157230-67-6)
• EPA Substance Registry System: DEPMPO(157230-67-6)

Safety Data

• Hazardous Substances Data: 157230-67-6(Hazardous Substances Data)

Usage

Description

DEPMPO (157230-67-6) is a spin trap capable of detecting oxygen, nitrogen, sulfur and carbon-centered free radicals both in vitro and in vivo. DEPMPO is useful for distinguishing between superoxide-dependent pathways of hydroxyl radical generation, and those that are superoxide independent.

Chemical Properties

DEPMPO is Pale Yellow Oil

Uses

Different sources of media describe the Uses of 157230-67-6 differently. You can refer to the following data:
1. DEPMPO is the most efficient spin trap for the in vitro detection of O-, N-, S- and C-centered free radicals both invitro and invivo. It has a longer life-time than DMPO and can distinguish between superoxide-dependent and independent mechanisms that lead to the hydroxyl radical. It is less lipophilic (Kp=0.16) than DIPPMPO.
2. DEPMPO is a spin trap useful as a probe for free radical formation during myocardial ischemia/reperfusion injury. An analogue of DMPO

References

1) Liu et al. (1999), Evaluation of DEPMPO as a spin trapping agent in biological systems; Free Radic. Biol. Med., 26 714 2) Shi et al. (2005), Evaluation of spin trapping agents and trapping conditions for detection of cell-generated reactive oxygen species; Arch. Biochem. Biophys., 437 59 3) Culcasi et al. (2012), EPR spin trapping evaluation of ROS production in human fibroblasts exposed to cerium oxide nanoparticles: evidence for NADPH oxidase and mitochondrial stimulation; Chem. Biol. Interact., 199 161 4) Tampieri et al. (2019), Comment on “Water Soluble Fluorescent Probe with Dual Mitochondria/Lysosome Targetability for Selective Superoxide Detection in Live Cells and in Zebrafish Embryos; ACS Sens. E-pub. Ahead of Print [Focus Citation]

InChI:InChI=1/C9H18NO4P/c1-4-13-15(12,14-5-2)9(3)7-6-8-10(9)11/h8H,4-7H2,1-3H3

Upstream product

• 189149-51-7 Diethyl (1-hydroxy-2-methylpyrrolidin-2-yl)phosphonate 
• 257612-81-0 Diethyl (2-methylpyrrolin-2-yl)phosphonate 
• 5891-21-4 5-chloro-2-pentanone 
• 872-32-2 2-methyl-1H-pyrroline 
• 157230-68-7 diethyl (2-methyl-2-pyrrolidinyl)phosphonate 
• 163273-61-8 NOC₅H₈PO₃C₄H₁₀O₂H 

Downstream Products

• 163273-61-8 NOC₅H₈PO₃C₄H₁₀O₂H 

Relevant articles and documents

Synthesis and use as spin-trap of 5-methyl-5-phosphono-1-pyrroline N-oxide (DHPMPO). pH Dependence of the EPR parameters of the spin adducts

5-Methyl-5-phosphono-1-pyrroline N-oxide (DHPMPO), the acid analogue of DEPMPO, is synthesized by hydrolysis of the diethoxyphosphoryl moiety of DEPMPO. A variety of carbon- and oxygen-centred radicals are trapped with DHPMPO and the corresponding EPR spe

5-(Diethoxyphosphoryl)-5-methyl-1-pyrroline N-Oxide: A New Efficient Phosphorylated Nitrone for the in Vitro and in Vivo Spin Trapping of Oxygen-Centered Radicals

5-(Diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide (DEPMPO, 2), a new spin trap, has been synthesized via a two-step synthetic route, and its ability to spin trap oxy radicals in biological milieu has been addressed.The in vitro spin trapping of hydroxyl and superoxide radicals was investigated in a phosphate buffer 0.1 M, and the hyperfine coupling constants of the spin adducts were determined.The rates of spin trapping of hydroxyl and superoxide radicals with 2 were found to be close to those reported for 5,5-dimethyl-1-pyrroline N-oxide (DMPO).However, the DEPMPO-superoxide spin adduct was shown to be significantly more persistent (15 times at pH 7) than the DMPO-superoxide spin adduct.Using 2 as a spin trap, the production of superoxide has been clearly characterized during the reperfusion of ischemic isolated rat hearts.

31P-Labeled pyrroline N-oxides: Synthesis of 5-diethylphosphono-5- methyl-1-pyrroline N-oxide (DEPMPO) by oxidation of diethyl (2- methylpyrrolidin-2-yl)phosphonate

The synthesis of DEPMPO from diethyl (2-methylpyrrolidin-2- yl)phosphonate (3), prepared by the addition of diethyl phosphite to 2- methylpyrroline, was carried out using different oxidation reagents: H2O2, m-CPBA, Oxone, 2-phenylsulfonyl-3-phenyloxaziridine (PSPO), dimethyldioxirane (DMD) and N-methylmorpholine N-oxide with catalytic amounts of tetrapropylammonium perruthenate (NMO/TPAP). The highest yield of DEPMPO (>80%) was obtained using two equivalents of PSPO or DMD. Different compounds involved in the oxidation of 3 have been isolated and characterized.

Decay of the Hydroperoxyl Spin Adduct of 5-Diethoxyphosphoryl-5-methyl-1-pyrroline N-Oxide: an EPR Kinetic Study

The decay kinetics of the hydroperoxyl spin adduct of both 5-diethoxyphosphoryl-5-methyl-1-pyrroline N-oxide (DEPMPO), a new β-phosphorylated cyclic nitrone and 5,5-dimethyl-1-pyrroline N-oxide (DMPO) were studied in various media by EPR spectroscopy.In organic solvents, both first- and second-order processes were shown to contribute to the decay of the two spin adducts.However, in aqueous solution the DMPO-hydroperoxyl spin adduct decay was pure first-order.The half-lives of the two spin adducts were determined in every medium tested and the DEPMPO-hydroperoxyl spin adduct was shown to be significantly more persistent (from five times in organic solvents to 30 times in a pH 5.6 buffer) than the DMPO-hydroperoxyl spin adduct.