934182-09-9

Basic information

• Product Name: 2-(5,5-Dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yl)-2-methyl-3,4-dihydro-2H-pyrrole 1-oxide, 5-(2,2-Dimethyl-1,3-propoxy cyclophosphoryl)-5-methyl-1-pyrroline N-oxide
• Synonyms: 2-(5,5-Dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yl)-2-methyl-3,4-dihydro-2H-pyrrole 1-oxide, 5-(2,2-Dimethyl-1,3-propoxy cyclophosphoryl)-5-methyl-1-pyrroline N-oxide;CYPMPO;2-(5,5-Dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yl)-2-methyl-3,4-dihydro-2H-pyrrole 1-oxide;5-(2,2-Dimethyl-1,3-propoxy cyclophosphoryl)-5-methyl-1-pyrroline N-oxide;OSKIWEPJAIOTFB-UHFFFAOYSA-N
• CAS NO: 934182-09-9
• Molecular Formula: C10H18NO4P
• Molecular Weight: 247.229
• Mol File: 934182-09-9.mol

Chemical Properties

• Appearance: /
• Storage Temp.: −20°C
• Solubility: Soluble in DMSO (up to 20 mg/ml), in DMF (up to 25 mg/ml) or in PBS-pH 7.2 (up to 10 mg/ml).
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or DMF may be stored at -20° for up to 3 months. Aqueous solutions are not stable and must be used within one working day.
• CAS DataBase Reference: 2-(5,5-Dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yl)-2-methyl-3,4-dihydro-2H-pyrrole 1-oxide, 5-(2,2-Dimethyl-1,3-propoxy cyclophosphoryl)-5-methyl-1-pyrroline N-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(5,5-Dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yl)-2-methyl-3,4-dihydro-2H-pyrrole 1-oxide, 5-(2,2-Dimethyl-1,3-propoxy cyclophosphoryl)-5-methyl-1-pyrroline N-oxide(934182-09-9)
• EPA Substance Registry System: 2-(5,5-Dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yl)-2-methyl-3,4-dihydro-2H-pyrrole 1-oxide, 5-(2,2-Dimethyl-1,3-propoxy cyclophosphoryl)-5-methyl-1-pyrroline N-oxide(934182-09-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 934182-09-9(Hazardous Substances Data)

Usage

Uses

Used in Free Radical Trapping Applications:
CYPMPO is used as a free radical spin-trap for capturing hydroxyl and superoxide free radicals. Its improved solubility and longer half-life in aqueous buffers make it a practical choice for experiments involving free radical detection and analysis.
Used in Research and Development:
CYPMPO is utilized in research and development for studying the behavior of free radicals and their interactions with various compounds. Its enhanced properties compared to DEPMPO allow for more efficient and accurate measurements in experimental settings.
Used in Pharmaceutical and Chemical Industries:
CYPMPO can be employed in the pharmaceutical and chemical industries for the development of new drugs and chemical compounds that target free radicals. Its unique properties make it a valuable tool for designing and testing new molecules with potential therapeutic applications.
Used in Environmental and Analytical Chemistry:
CYPMPO can be applied in environmental and analytical chemistry for the detection and quantification of free radicals in various samples. Its effectiveness in trapping free radicals makes it a useful tool for assessing the presence and impact of these reactive species in different environments.

References

1) Kamibayashi?et al. (2006)?Synthesis and characterization of a practically better DEPMPO-type spin trap, 5-(2,2-dimethyl-1,3-propoxycyclophosphoryl)-5-methyl-1-pyrroline N-oxide (CYPMPO); Free Radic. Res.?40?1166

Upstream product

• 4090-60-2 5,5-dimethyl-1,3-dioxaphosphorinan-2-oxide 
• 902503-51-9 2-methyl-2-(5,5-dimethyl-2-oxo-1,3,2-dioxaphosphinan-2-yl)pyrrolidine 

Relevant articles and documents

Spin-trapping reactions of a novel gauchetype radical trapper G-CYPMPO

Chemical reactions of a novel gauchetype spin trap, G-CYPMPO (sc-5-(5,5-dimethyl-2-oxo-1,3,2-dioxaphosphinan-2-yl)-5-methy-1-pyrroline N-oxide, O1-P1-C6-N1 torsion angle = 52.8°), with reactive oxygen species were examined by pulse radiolysis technique with 35 MeV electron beam and by electron spin resonance spectroscopy after 60Co γ-ray irradiation. The spin-trapping reaction rate constants of G-CYPMPO toward the hydroxyl radical and the hydrated electron were estimated to be (4.2 ± 0.1) × 109 and (11.8 ± 0.2) × 109 M-1s-1, respectively. Half-lives of the spin adducts, hydroxyl radical, and perhydroxyl radical adducted G-CYPMPO were estimated to be ～35 and ～90 min, respectively. A comparison of the results with earlier reports using different radical sources suggests that the purity of the solution and/or the radical generation technique may influence the stability of the spin adducts.

CyDEPMPOs: A class of stable cyclic DEPMPO derivatives with improved properties as mechanistic markers of stereoselective hydroxyl radical adduct formation in biological systems

The cis/trans diastereoisomeric composition of hydroxyl radical adducts to chiral cyclic nitrones can be used to approach mechanisms of free radical formation in biological systems. Such determination is greatly simplified when both diastereoisomers have ESR spectra with at least two non-overlapping lines. To achieve this prerequisite, a series of DEPMPO-derived spin traps bearing one unsubstituted or alkyl-substituted 2-oxo-1,3,2-dioxaphosphorinane ring were synthesized and their structures were confirmed by X-ray diffraction, 1H, 13C and 31P NMR. These CyDEPMPOs nitrones showed variable lipophilicities and LD50 values on murine fibroblasts compatible with a safe use in biological spin trapping. All CyDEPMPOs formed persistent spin adducts with a series of free radicals, including superoxide and hydroxyl (i.e., CyDEPMPOs-OH) and the in vitro half-life times of these two latter were at least as extended as those of parent DEPMPO. Using four methods of CyDEPMPOs-OH formation, the cis-CyDEPMPOs-OH percentage was found significantly varied with substitution on the P-containing ring and, more interestingly, with the generating system.