3,4-Dihydro-2,2-dimethyl-2H-pyrrol-1-oxid Chemische Eigenschaften,Einsatz,Produktion Methoden
S-Sätze Betriebsanweisung:
S24/25:Berührung mit den Augen und der Haut vermeiden.
Beschreibung
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.
Chemische Eigenschaften
white to faintly yellow solid
Verwenden
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.
synthetische
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 H
1 NMR (400 MH CDC1
3, Me
4Si) is 6.80 (t, 2H, methylene bound to quaternary C, J = 7.2Hg), 1.43 (s, 6H, methyl), C
13NMr (100 MH2, CDC13, Me
4 Si) 5=132.4 (Vinyl), 73.5 (quaternary), 34.1 (Allyl), 25.3 (methylene bound to quaternary C), 24.4 (methyls).
Biologische Aktivität
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.
3,4-Dihydro-2,2-dimethyl-2H-pyrrol-1-oxid Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
