A water-soluble azo compound used as a free radical generator
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AAPH

Item No. 82235

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,2'-azobis-2-methyl-propanimidamide, dihydrochloride
CAS Number
2997-92-4
Molecular Formula
C8H18N6 • 2HCl
Formula Weight
271.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 10 mg/ml
SMILES
N/C(C(C)(C)/N=N/C(C)(C)/C(N)=N\[H])=N/[H].Cl.Cl
InChi Code
InChI=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
LXEKPEMOWBOYRF-QDBORUFSSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 g

    $70

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    10 g

    $117

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    Product 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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Noguchi, N., Takahashi, M., Tsuchiya, J., et al. Action of 21-aminosteroid U74006F as an antioxidant against lipid peroxidation. Biochem. Pharmacol. 55(6), 785-791 (1998).

    2. Liu, Z.Q., Yu, W., and Liu, Z.L. Antioxidative and prooxidative effects of coumarin derivatives on free radical initiated and photosensitized peroxidation of human low-density lipoprotein. Chem. Phys. Lipids 103(1-2), 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(4), 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(17), 4032-4038 (2000).