AAPH

Cayman Chemical Item Number 82235

(CAS 2997-92-4)

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Description

AAPH is a water-soluble azo compound which is used extensively as a free radical generator, often in the study of lipid peroxidation and the characterization of antioxidants.1,2,3,4 Decomposition of AAPH produces molecular nitrogen and 2 carbon radicals. The carbon radicals may combine to produce stable products or react with molecular oxygen to give peroxyl radicals. The half-life of AAPH is about 175 hours (37°C at neutral pH), making the rate of free radical generation essentially constant during the first several hours in solution.5 While AAPH may be used effectively for lipid peroxidation in aqueous dispersions of fatty acids, other radical generators may be better suited for peroxidation studies in lipid micelles or membranes.6,7

1. Noguchi, N., Takahashi, M., Tsuchiya, J., et al. Action of 21-aminosteroid U74006F as an antioxidant against lipid peroxidation. Biochem Pharmacol 55 785-791 (1998).

2. Liu, Z., Yu, W., and Liu, Z. Antioxidative and prooxidative effects of coumarin derivatives on free radical initiated and photosensitized peroxidation of human low-density lipoprotein. Chem Phys Lipids 103 125-135 (1999).

3. Rice-Evans, C., and Miller, N. Total antioxidant status in plasma and body fluids. Methods Enzymol 234(24) 279-293 (1994).

4. Liégeois, C., Lermusieau, G., and Collin, S. Measuring antioxidant efficiency of wort, malt, and hops against the 2,2'-azobis(2-amidinopropane) dihydrochloride-induced oxidation of an aqueous dispersion of linoleic acid. J Agric Food Chem 48 1129-1134 (2000).

5. Niki, E. Free radical initiators as source of water- or lipid-soluble peroxyl radicals. Methods Enzymol 186 100-108 (1990).

6. Yamamoto, Y., Haga, S., Niki, E., et al. Oxidation of lipids. V. Oxidation of methyl linoleate in aqueous dispersion. Bull Chem Soc Jpn 57(5) 1260-1264 (1984).

7. Culbertson, S.M., and Porter, N.A. Unsymmetrical azo initiators increase efficiency of radical generation in aqueous dispersions, liposomal membranes, and lipoproteins. J Am Chem Soc 122 4032-4038 (2000).

Formal Name 2,​2'-​azobis-​2-​methyl-​propanimidamide,​ dihydrochloride
CAS Number 2997-92-4
Molecular Formula C8H18N6 • 2HCl
Formula Weight 271.2
Formulation A crystalline solid
Purity ≥98%
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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N/C(C(C)​(C)​/N=N/C(C)​(C)​/C(N)​=N\[H]​)​=N/[H]​.Cl.Cl
InCHI Code
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​1S/C8H18N6.2ClH/c1-7(2,5(9)​10)​13-14-8(3,4)​6(11)​12;;/h1-4H3,(H3,9,10)​(H3,11,12)​;2*1H/b14-13+;;
InCHI Key
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LXEKPEMOWBOYRF-QDBORUFSSA-N

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Size Price Quantity Subtotal
1 g $11.00 $0.00
5 g $50.00 $0.00
10 g $88.00 $0.00
25 g $193.00 $0.00
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Cayman Chemical Company regularly evaluates our shipping methods to ensure product stability is maintained and our corporate environmental impact is minimized. Products selected for review are evaluated and shipping methods are certified by our Scientists. While occasionally our method of shipping a product may change, rest assured the shipping conditions on all Cayman Chemical products have been reviewed and validated.

Upon receipt, it is important to check the storage requirements of your products and place them at the appropriate temperature. Products shipped without ice may require frozen storage for long term stability.

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