5,5-DIMETHYL-1-PYRROLINE N-OXIDE CAS 3317-61-1

Introduction：Basic information about 5,5-DIMETHYL-1-PYRROLINE N-OXIDE CAS 3317-61-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

5,5-DIMETHYL-1-PYRROLINE N-OXIDE Basic information

• Product Name: 5,5-DIMETHYL-1-PYRROLINE N-OXIDE
• Synonyms: DMPO;5,5-DIMETHYL-1-PYRROLINE N-OXIDE;2,2-DIMETHYL-3,4-DIHYDRO-2H-PYRROLE 1-OXIDE;3,4-DIHYDRO-2,2-DIMETHYL-2H-PYRROLE 1-OXIDE;3,4-Dihydro-2,2-dimethyl-2H-pyrrole N-oxide 95%;2,2-Dimethyl-3,4-Dihydro-2H-Pyrrole 1-Ox;5,5-dimethyl-1-pyrroline-1-oxide;5,5-Dimethyl-1-pyrroline N-oxide [spin trapping
• CAS: 3317-61-1
• MF: C6H11NO
• MW: 113.16
• EINECS: 222-011-1
• Product Categories: pharmacetical;Analytical Chemistry;ESR Spectrometry;Spin Trapping Reagents
• Mol File: 3317-61-1.mol

5,5-DIMETHYL-1-PYRROLINE N-OXIDE Chemical Properties

• Melting point: 25-29 °C (lit.)
• Boiling point: 75 °C/0.4 mmHg (lit.)
• density: 1.015 g/mL at 25 °C (lit.)
• refractive index: n20/D 1.496(lit.)
• Fp: 204 °F
• storage temp.: -20°C
• solubility: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
• pka: 2.47±0.40(Predicted)
• form: Pale yellow solid or oil.
• color: Pale yellow
• Merck: 14,3393
• BRN: 107603
• Stability: Stable, but light sensitive, hygroscopic and heat sensitive. Store in the dark, under an inert gas, and keep cold. Incompatible with strong oxidizing agents, moisture.
• InChI: 1S/C6H11NO/c1-6(2)4-3-5-7(6)8/h5H,3-4H2,1-2H3
• InChIKey: VCUVETGKTILCLC-UHFFFAOYSA-N
• SMILES: CC1(C)CCC=[N+]1[O-]
• CAS DataBase Reference: 3317-61-1(CAS DataBase Reference)

Safety Information

• Safety Statements: 24/25
• WGK Germany: 3
• F: 8-10
• HazardClass: IRRITANT
• HS Code: 29339900
• Storage Class: 10 - Combustible liquids

5,5-DIMETHYL-1-PYRROLINE N-OXIDE Usage And Synthesis

Description

Free radicals are highly reactive, short-lived species. Spin traps react with radicals, forming stable adducts that can be further studied. DMPO is a commonly-used spin trap that reacts with O-, N-, S-, and C-centered radicals. This allows their characterization when used in association with electron spin resonance and immuno-spin trapping. DMPO is water-soluble, rapidly penetrates lipid bilayers, has low toxicity, and can be used in vitro and in vivo.

Chemical Properties

white to faintly yellow solid

Uses

Spin trap agent for biological systems.

Uses

5,5-Dimethyl-1-pyrroline N-oxide has been used as a spin trapping reagent to detect free radicals in electron paramagnetic resonance (EPR) based reactions.

Uses

5,5-Dimethyl-1-pyrroline N-oxide is a reagent generally used either as a free-radical spin-trapping agent, or electrophilic component during the synthesis of pyrrolidine derivatives. It may also be considered as 1,3-dipole in cycloaddition processes.

Definition

ChEBI: 5,5-dimethyl-1-pyrroline N-oxide is a member of the class of 1-pyrroline nitrones (1-pyrroline N-oxides) resulting from the formal N-oxidation of 5,5-dimethyl-1-pyrroline. Used as a spin trap for the study of radicals formed by enzymatic acetaldehyde oxidation. It has a role as a neuroprotective agent and a spin trapping reagent. It is functionally related to a 5,5-dimethyl-1-pyrroline.

Preparation

To a three-necked round bottom flask equipped with a condenser, addi­tion funnel, thermometer, and mechanical stirrer and containing 300 ml. 95% ethanol precooled to 2°C is added, all at once, 14.5 g (0.1 mole) 4-methyl-4-nitropentanol, and 13.1 g (1.2 mole) zinc dust. With rapid agita­tion, the glacial acetic acid (24.0 g, 0.4 mole) is added dropwise over a 1-hr period while maintaining the reaction temperature below 15°C. The mix­ture is stirred vigorously for 2 hr and then stored in the refrigerator for 2 days, at approximately 1°C. Then the zinc acetate is filtered and rinsed with 100 ml of ethanol. The combined ethanol factions are rotoevapo-rated to give the crude nitrone. The crude nitrone is dissolved in a 200 ml portion of dichloromethane and the latter washed two times with saturated sodium bicarbonate solution. The organic layer is dried over sodium sul­fate and the solvent rotoevaporated, to give 10.7 (94% yield) of the crude nitrone. The product was purified by double distillation (b.p. 53°C, 0.1 Torr), to give 6.8 g (60%) of the pure nitrone as a white hygroscopic solid. The H¹ NMR (400 MH CDC1₃, Me₄Si) is 6.80 (t, 2H, methylene bound to quaternary C, J = 7.2Hg), 1.43 (s, 6H, methyl), C¹³NMr (100 MH2, CDC13, Me₄ Si) 5=132.4 (Vinyl), 73.5 (quaternary), 34.1 (Allyl), 25.3 (methylene bound to quaternary C), 24.4 (methyls).

Biological Activity

Water soluble nitric oxide spin trap; allows the measurement of oxygen-centered free radicals in biological systems at room temperature using electron spin resonance (ESR). Has a high reaction rate constant for superoxide and hydroxyl radicals, and distinguishes simultaneously among a variety of important biologically generated free radicals.

Physiological effects

5,5-dimethyl-1-pyrroline N-oxide is used as a spin trap for the study of radicals formed by enzymatic acetaldehyde oxidation. It has a role as a neuroprotective agent and a spin trapping reagent.

References

[1] CHIHO NISHIZAWA. Hydroxyl radical generation caused by the reaction of singlet oxygen with a spin trap, DMPO, increases significantly in the presence of biological reductants.[J]. Free Radical Research, 2004, 38 4: 385-392. DOI:10.1080/1071576042000191772
[2] HONGLIAN SHI . Evaluation of spin trapping agents and trapping conditions for detection of cell-generated reactive oxygen species[J]. Archives of biochemistry and biophysics, 2005, 437 1: Pages 59-68. DOI:10.1016/j.abb.2005.02.028
[3] JEAN-LOUIS CLÉMENT. Assignment of the EPR Spectrum of 5,5-Dimethyl-1-pyrroline N-Oxide (DMPO) Superoxide Spin Adduct†[J]. The Journal of Organic Chemistry, 2005, 70 4: 1198-1203. DOI:10.1021/jo048518z
[4] SANDRA E. GOMEZ-MEJIBA . Immuno-spin trapping of protein and DNA radicals: “Tagging” free radicals to locate and understand the redox process[J]. Free Radical Biology and Medicine, 2009, 46 7: Pages 853-865. DOI:10.1016/j.freeradbiomed.2008.12.020

5,5-DIMETHYL-1-PYRROLINE N-OXIDE Preparation Products And Raw materials

• Preparation Products: 4-METHYLPHTHALIMIDE 99