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

5,5-DIMETHYL-1-PYRROLINE N-OXIDE structure

CAS No.: 3317-61-1

Chemical Name:: 5,5-DIMETHYL-1-PYRROLINE N-OXIDE

Synonyms: DMPO;2,2-DIMETHYL-3,4-DIHYDRO-2H-PYRROLE 1-OXIDE;5,5-dimethyl-1-pyrroline-1-oxide;3,4-DIHYDRO-2,2-DIMETHYL-2H-PYRROLE 1-OXIDE;Dimethyl N;spintrappingreagent;,5-Dimethyl-1-pyrroline N-oxide;5,5-DIMETHYL-1-PYRROLINE N-OXIDE;5,5-Dimethyl-1-Pyrrolidine-N-oxide;5,5-Dimethyl-1-pyrrolineN-Oxide>

CBNumber:: CB3290637

Molecular Formula:: C6H11NO

Molecular Weight:: 113.16

MDL Number:: MFCD00005279

MOL File:: 3317-61-1.mol

MSDS File:: SDS

Last updated:2023-06-08 17:06:37

Request For Quotation

5,5-DIMETHYL-1-PYRROLINE N-OXIDE 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.)
Flash point	204 °F
storage temp.	-20°C
solubility	Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
form	Pale yellow solid or oil.
pka	2.47±0.40(Predicted)
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.
InChIKey	VCUVETGKTILCLC-UHFFFAOYSA-N
CAS DataBase Reference	3317-61-1(CAS DataBase Reference)
FDA UNII	7170JZ1QF3

SAFETY

Risk and Safety Statements

Symbol(GHS)

GHS07

Signal word

Warning

Hazard statements

H315-H319-H335

Precautionary statements

P280-P305+P351+P338-P321

Safety Statements

24/25

WGK Germany

8-10

HazardClass

IRRITANT

HS Code

29339900

NFPA 704

	1
0		0

5,5-DIMETHYL-1-PYRROLINE N-OXIDE price More Price(32)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	92688	5,5-Dimethyl-1-pyrroline N-oxide for ESR-spectroscopy	3317-61-1	100mg	$149	2024-03-01	Buy
TCI Chemical	D2362	5,5-Dimethyl-1-pyrroline N-Oxide >97.0%(GC)(T)	3317-61-1	1g	$128	2024-03-01	Buy
TCI Chemical	D2362	5,5-Dimethyl-1-pyrroline N-Oxide >97.0%(GC)(T)	3317-61-1	5g	$468	2024-03-01	Buy
Cayman Chemical	10006436	DMPO ≥98%	3317-61-1	500mg	$62	2024-03-01	Buy
Cayman Chemical	10006436	DMPO ≥98%	3317-61-1	1g	$115	2024-03-01	Buy

Product number	Packaging	Price	Buy
92688	100mg	$149	Buy
D2362	1g	$128	Buy
D2362	5g	$468	Buy
10006436	500mg	$62	Buy
10006436	1g	$115	Buy

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

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

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.

Uses

Spin trap agent for biological systems.

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).
Preparation of 5,5-dimethyl-l-pyrroline-N-oxide

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) Nishizawa et al. (2004), Hydroxyl radical generation caused by the reaction of singlet oxygen with the spin trap DMPO, increases significantly in the presence of biological reductants; Mol. Pharmacol., 6 597 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) Clement et al. (2005), Assignment of the EPR spectrum of 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) superoxide spin adduct; J. Org. Chem., 70 1198 4) Gomez-Mejiba et al. (2009), Immuno-spin trapping of protein and DNA radicals: ‘tagging’ free radicals to locate and understand the redox process; Free Rad. Biol. Med., 42 530

5,5-DIMETHYL-1-PYRROLINE N-OXIDE synthesis

Synthesis of 5,5-DIMETHYL-1-PYRROLINE N-OXIDE from 4-METHYL-4-NITROVALERALDEHYDE

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

Raw materials

Preparation Products

4-METHYLPHTHALIMIDE 99

5,5-DIMETHYL-1-PYRROLINE N-OXIDE Suppliers

Global( 214)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Alfa Chemistry	+1-5166625404	Info@alfa-chemistry.com	United States	21317	58
Capot Chemical Co.,Ltd.	571-85586718 +8613336195806	sales@capotchem.com	China	29797	60
Shanghai Daken Advanced Materials Co.,Ltd	+86-371-66670886	info@dakenam.com	China	15371	58
Nanjing ChemLin Chemical Industry Co., Ltd.	025-83697070	product@chemlin.com.cn	CHINA	3012	60
Accela ChemBio Inc.	(+1)-858-699-3322	info@accelachem.com	United States	19965	58
Chongqing Chemdad Co., Ltd	+86-023-61398051 +8613650506873	sales@chemdad.com	China	39916	58
CONIER CHEM AND PHARMA LIMITED	+8618523575427	sales@conier.com	China	47465	58
career henan chemical co	+86-0371-86658258 15093356674;	factory@coreychem.com	China	29826	58
TargetMol Chemicals Inc.	+1-781-999-5354 +1-00000000000	marketing@targetmol.com	United States	19892	58
Hefei TNJ Chemical Industry Co.,Ltd.	0551-65418671	sales@tnjchem.com	China	34572	58

Supplier	Advantage
Alfa Chemistry	58
Capot Chemical Co.,Ltd.	60
Shanghai Daken Advanced Materials Co.,Ltd	58
Nanjing ChemLin Chemical Industry Co., Ltd.	60
Accela ChemBio Inc.	58
Chongqing Chemdad Co., Ltd	58
CONIER CHEM AND PHARMA LIMITED	58
career henan chemical co	58
TargetMol Chemicals Inc.	58
Hefei TNJ Chemical Industry Co.,Ltd.	58

View Lastest Price from 5,5-DIMETHYL-1-PYRROLINE N-OXIDE manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2021-07-13	5,5-Dimethyl-1-pyrroline N-oxide 3317-61-1	US $15.00-10.00 / KG	1KG	99%+ HPLC	Monthly supply of 1 ton	Zhuozhou Wenxi import and Export Co., Ltd
2021-07-10	5,5-Dimethyl-1-pyrroline N-oxide 3317-61-1	US $15.00-10.00 / KG	1KG	99%+ HPLC	Monthly supply of 1 ton	Zhuozhou Wenxi import and Export Co., Ltd
2019-12-25	5,5-DIMETHYL-1-PYRROLINE N-OXIDE 3317-61-1	US $1.00 / g	1g	99%	1000KGS	Career Henan Chemical Co

5,5-Dimethyl-1-pyrroline N-oxide
3317-61-1
US $15.00-10.00 / KG
99%+ HPLC
Zhuozhou Wenxi import and Export Co., Ltd

5,5-Dimethyl-1-pyrroline N-oxide
3317-61-1
US $15.00-10.00 / KG
99%+ HPLC
Zhuozhou Wenxi import and Export Co., Ltd

5,5-DIMETHYL-1-PYRROLINE N-OXIDE
3317-61-1
US $1.00 / g
99%
Career Henan Chemical Co

5,5-DIMETHYL-1-PYRROLINE N-OXIDE Spectrum

5,5-DIMETHYL-1-PYRROLINE N-OXIDE(3317-61-1)¹HNMR 5,5-DIMETHYL-1-PYRROLINE N-OXIDE(3317-61-1)IR 5,5-DIMETHYL-1-PYRROLINE N-OXIDE(3317-61-1)FT-IR 5,5-DIMETHYL-1-PYRROLINE N-OXIDE(3317-61-1)Raman

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5,5-DIMETHYL-1-PYRROLINE N-OXIDE 5,5-Dimethyl-1-pyrroline N-oxide [spin trapping spintrappingreagent 1-Oxylato-2,2-dimethyl-3,4-dihydro-2H-pyrrole-1-ium 3,4-Dihydro-1-oxylato-2,2-dimethyl-2H-pyrrolium 5,5-Dimethyl-1-Pyrrolidine-N-oxide 5,5-DIMETHYL-1-PYRROLINE N-OXIDE, [SPIN TRAPPING REAGENT] 5,5-DIMETHYL-1-PYRROLINE N-OXIDE [SPIN TRAPPING REAGENT] 97+% 5,5-DIMETHYL-1-PYRROLINE N-OXIDE 99% 2,2-dimethyl-1-oxidanidyl-3,4-dihydropyrrol-1-ium 2,2-dimethyl-1-oxido-1-pyrrolin-1-ium 2,2-dimethyl-1-oxido-3,4-dihydropyrrol-1-ium 5,5-Dimethyl-1-pyrroline N-oxide ,97% 5,5-Dimethyl-1-pyrroline N-oxide,DMPO 2,2-diMethyl-2,3-dihydro-1H-pyrrole 1-oxide ,5-Dimethyl-1-pyrroline N-oxide Dimethyl N 5,5-Dimethyl-1-pyrrolineN-Oxide> 2,2-Dimethyl-3,4-Dihydro-2H-Pyrrole 1-Ox 3,4-Dihydro-2,2-dimethyl-2H-pyrrole N-oxide 95% DMPO 2,2-DIMETHYL-3,4-DIHYDRO-2H-PYRROLE 1-OXIDE 5,5-dimethyl-1-pyrroline-1-oxide 3,4-DIHYDRO-2,2-DIMETHYL-2H-PYRROLE 1-OXIDE 5,5-Dimethyl-1-pyrroline N-Oxide, ≥ 97.0% 3317-61-1 Enzymes, Inhibitors, and Substrates Pyrrolines Nitric Oxide Metabolism Nitric Oxide Scavengers ESR Spectrometry Spin Trapping Reagents Building Blocks Biochemicals and Reagents Application Index BioChemical Cell Signaling Enzymes Heterocyclic Building Blocks pharmacetical Analytical Chemistry ESR Spectrometry Spin Trapping Reagents