2,2-Azobis[2-(2-imidazolin-2-yl)propane]

• CAS: 20858-12-2
• Catalog Number: ACM20858122
• Category: Main Products
• Molecular Weight: 250.34
• Molecular Formula: C₁₂H₂₂N₆
• Synonyms: 2,2-AZOBIS[2-(2-IMIDAZOLIN-2-YL)PROPANE];2,2'-[azobis(1-methylethylidene)]bis[4,5-dihydro-1h-imidazol;2,2-(azodiisopropylidene)bis[4,5-dihydro-1H-imidazole];2,2-Azobis-(N,N-dimethyleneisobutyramidine);2,2-[Azobis(dimethylmethylene)]bis(2-imidazoline);2,2-[Azobis(propane-2,2-diyl)]bis(2-imidazoline);2,2-Azobis(1-methyl-1,1-ethanediyl)bis(2-imidazoline);2,2-Bis(2-imidazolin-2-yl)[2,2-azobispropane]
• IUPAC Name: bis[2-(4,5-dihydro-1H-imidazol-2-yl)propan-2-yl]diazene
• Canonical SMILES: CC(C)(C1=NCCN1)N=NC(C)(C)C2=NCCN2
• InChI Key: LWMFAFLIWMPZSX-UHFFFAOYSA-N
• Boiling Point: 413.3ºC at 760mmHg
• Density: 1.22g/cm³
• EC Number: 244-085-4
• Exact Mass: 250.19100
• H-Bond Acceptor: 6
• H-Bond Donor: 2

Case Study

pH dependence of lipid peroxidation rates with 2,2-azobis[2-(2-imidazolin-2-yl)propane] as initiator

Hanlon, Mary C., and David W. Seybert. Free Radical Biology and Medicine 23.5 (1997): 712-719.

The pH dependence of lipid peroxidation rates in methyl linoleate/Triton mixed micelles using a series of water-soluble azo initiators is reported. The cationic initiators 2,2*-azobis(2-amidinopropane) (ABAP) and 2,2-azobis[2-(2-imidazolin-2-yl)propane] (ABIP) exhibit similar behavior, where an increase in pH significantly increases the peroxidation rate. The rate data for ABAP and ABIP are consistent with a single proton equilibrium, with apparent kinetic pK values for the rates being approximately 7 and 6, respectively. The azo initiator 4,4*-azobis(4-cyanovaleric acid) (ABCPA), which generates negatively charged radicals upon thermolysis at neutral pH, was also studied. In contrast to the effects observed for ABAP and ABIP, the peroxidation rate of ABCPA exhibited an inverse pH dependence, where the peroxidation rate increased with decreasing pH, with an apparent pK of approximately 5.
All pH values are quoted at the temperature at which the peroxidation experiments were performed (37 °C or 50 °C). Aqueous solutions of the initiator ABAP, 2,2-azobis[2-(2-imidazolin-2-yl)propane] (ABIP), and ABCPA were prepared at room temperature along with buffer of appropriate concentration. The pH was adjusted at room temperature using the known buffer temperature coefficient to achieve the desired pH at the peroxidation temperature. The total ionic strength was maintained at 100 mM by adding sufficient NaCl to all peroxidation reaction mixtures. Solutions of azo initiator/buffer/sodium chloride were maintained at 47 °C until the start of the experiment. Direct measurements of pH at higher temperatures confirmed that the actual pH was generally within <0.05 pH units of the value calculated based on the room temperature pH and the buffer temperature coefficient. The final buffer concentration in all experiments was 50 mM.

2,2'-Azobis[2-(2-imidazolin-2-yl)propane] for the antioxidant activity of resveratrol

Fabris, Sabrina, et al. Biophysical chemistry 135.1-3 (2008): 76-83.

The antioxidant activities of trans-resveratrol (trans-3,5,4'-trihydroxystilbene) and trans-resveratrol (trans-5,4'-dihydroxystilbene-3-O-β-D-glucopyranoside) have been compared by measuring their inhibitory effects on linoleic acid (LA) peroxidation and free radical scavenging abilities against different free radicals such as DPPH and free radical initiators (2,2'-azobis[2-(2-imidazolin-2-yl)propane] (ABIP)). The two stilbenes were found to have similar antioxidant capacity, while a slower but longer lasting protective effect against lipid peroxidation was shown in comparison with BHT (2,6-di-tert-butyl-4-methylphenol) and α-tocopherol (vitamin E, vit. E). Furthermore, resveratrol appears to be more effective than resveratrol due to the reaction of the latter with its free radical form.
The antioxidant activity of resveratrol and resveratrol glycosides against LA peroxidation in sodium dodecyl sulfate (SDS) micelles and DPPC monolayer liposomes was investigated. The peroxidation reaction was initiated by the thermolabile water-soluble azo initiator 2,2'-azobis[2-(2-imidazolin-2-yl)propane] (ABIP) and measured as the rate of oxygen consumption. The reaction was carried out in a closed thermostatic vessel (37 °C) and the oxygen consumption was followed using a Clark electrode. The concentration of LA was 10 mM in SDS micelles (50 mM) and 2.5 mM in DPPC monolayer liposomes (20 mM).

2,2'-Azobis[2-(2-imidazolin-2-yl)propane] for the scavenging of peroxyl radicals by proanthocyanidins

Rigo, Adelio, et al. Journal of agricultural and food chemistry 48.6 (2000): 1996-2002.

The highly reactive free radical ROO was generated by 2,2'-azobis[2-(2-imidazolin-2-yl)propane] and linoleic acid. The ROO scavenging capacity of some Italian red wines was evaluated based on the changes in oxygen consumption. Under the experimental conditions, the time course of oxygen consumption showed two typical behaviors: tocopherol-like (type I) and gallic acid-like (type II). In general, the time course of wine was similar to that of gallic acid. The oxygen consumption rate was found to decrease exponentially with the amount of wine or gallic acid added to the test solution. On this basis, the peroxyl radical scavenging capacity of red wine was expressed by the content of gallic acid (S). The S value was found to be correlated with the total proanthocyanidin and total polyphenol content of some Italian red wines (p < 0.01). Proanthocyanidins extracted from seeds made a significant contribution to the peroxyl radical scavenging capacity of red wine, while interestingly, the chemical class of low molecular weight tannins that reacted with vanillin was not associated with the S value.
The reaction mixture was prepared by dissolving the test solution in 50 mM phosphate buffer (pH 7.4), 2.5 mM linoleic acid and 100 mM SDS. 3 mL of this test solution was continuously stirred in an oxygen measuring cell at 37 (0.1 °C). After 5 min, when thermal equilibrium was reached, 50 μL of 0.5 M 2,2'-azobis[2-(2-imidazolin-2-yl)propane] aqueous solution (final concentration 8.2 mM) was added and incubated for another 10 min to determine the oxygen consumption rate due to uninhibited auto-oxidation of linoleic acid, after which wine (0.5-50 μL) was added to the test solution and the rate of inhibition of the reaction was recorded. A similar procedure was used to measure the free radical scavenging capacity of various antioxidants. In this case, standard solutions of various antioxidant compounds were prepared by dissolving 10 mg of antioxidant in 10 mL of ethanol. The oxygen consumption rate was calculated from the slope of the oxygraph recordings based on the initial oxygen concentration. All assays were performed at 37°C.

Synergistic antioxidant effect of 2,2-azobis[2-(2-imidazolin-2-yl)propane] on linoleic acid peroxidation

Rossetto, Monica, et al. Archives of Biochemistry and Biophysics 408.2 (2002): 239-245.

The inhibitory effect of anthocyanidins on linoleic acid peroxidation in micelles was investigated in the presence and absence of (+)-catechin. The peroxidation reaction was initiated by thermal decomposition of 2,2-azobis[2-(2-imidazolin-2-yl)propane] and the peroxidation kinetics were followed by measuring the rate of oxygen consumption and the rate of disappearance of the antioxidant. Analysis of the antioxidant effect of various anthocyanidins alone or in the presence of catechins showed that catechins were relatively inefficient in inhibiting linoleic acid oxidation but regenerated the highly efficient antioxidants malvidin 3-glucoside and, to a lesser extent, peonidin 3-glucoside. The recycling of malvidin 3-glucoside by catechins greatly increased the antioxidant efficiency of both antioxidants. This protective mechanism appears to be specific for malvidin and peonidin 3-glucoside. The high unpaired spin density of the phenolic O atoms in the radicals generated by these anthocyanins, calculated by the semiempirical quantum chemical AM1 method, can explain the observed behavior.
The addition of azo compounds to a model system consisting of linoleic acid micelles and SDS provides a constant rate of peroxyl radical generation, establishing a constant consumption of dissolved oxygen ðR 10:5 0:9 lM O/minÞ. No significant changes in this rate were observed due to the peroxidation of linoleic acid until the oxygen present in the starting solution disappeared. In the same figure, curve e represents the uptake observed when the azo compounds are added to a buffer containing only 50 mM SDS. The oxygen consumption rate (about 1:7 0:3 lM O/min) is related to the reaction of the radicals generated by the decomposition of 2,2-azobis[2-(2-imidazolin-2-yl)propane] with molecular oxygen, leading to the formation of peroxyl radicals, which, in the presence of linoleic acid, initiate the peroxidation process. Considering the kinetic rate constant k 1/4 of 2:44 10 min for the decomposition of ABIP, an average of 0.43 molecules of O were consumed per radical generated from the azo compound.

Custom Q&A

What is the molecular formula of 2,2-Azobis[2-(2-imidazolin-2-yl)propane]?

The molecular formula is C12H22N6.

What is the molecular weight of 2,2-Azobis[2-(2-imidazolin-2-yl)propane]?

The molecular weight is 250.34 g/mol.

What is the IUPAC name of 2,2-Azobis[2-(2-imidazolin-2-yl)propane]?

The IUPAC name is bis[2-(4,5-dihydro-1H-imidazol-2-yl)propan-2-yl]diazene.

What is the InChI of 2,2-Azobis[2-(2-imidazolin-2-yl)propane]?

The InChI is InChI=1S/C12H22N6/c1-11(2,9-13-5-6-14-9)17-18-12(3,4)10-15-7-8-16-10/h5-8H2,1-4H3,(H,13,14)(H,15,16).

What is the InChIKey of 2,2-Azobis[2-(2-imidazolin-2-yl)propane]?

The InChIKey is LWMFAFLIWMPZSX-UHFFFAOYSA-N.

What is the canonical SMILES of 2,2-Azobis[2-(2-imidazolin-2-yl)propane]?

The canonical SMILES is CC(C)(C1=NCCN1)N=NC(C)(C)C2=NCCN2.

What is the CAS number of 2,2-Azobis[2-(2-imidazolin-2-yl)propane]?

The CAS number is 20858-12-2.

What is the EC number of 2,2-Azobis[2-(2-imidazolin-2-yl)propane]?

The EC number is 244-085-4.

How many hydrogen bond donor counts are there in 2,2-Azobis[2-(2-imidazolin-2-yl)propane]?

There are 2 hydrogen bond donor counts.

How many rotatable bond counts are there in 2,2-Azobis[2-(2-imidazolin-2-yl)propane]?

The number of rotatable bond counts is not provided in the reference.