LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

4-hydroperoxynonenal

Systematic Name

4-hydroperoxy-2E-nonenal

Synonyms

4-HPNE

LM ID

LMFA06000253

Formula

C₉H₁₆O₃

Exact Mass

Calculate m/z

172.109945

Sum Composition

FAL 9:1;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

4-hydroxy Nonenal (4-HNE) is a lipid peroxidation product derived from oxidized ω-6 polyunsaturated fatty acids, such as linoleic acid and arachidonic acid, that is widely used as a marker of oxidative stress.^1,2 4-HNE exhibits various biological activities such as cytotoxicity, growth inhibiting activity, genotoxicity, and chemotactic activity.^1,2,3 4-hydroperoxy 2-Nonenal is the immediate precursor of 4-HNE formed from the cleavage of ω-6 hydroperoxides.⁴ Analogous reactions are expected to occur with hydroperoxides from other ω-6 fatty acids, particularly arachidonic acid.

This information has been provided by Cayman Chemical

References

1. Pryor, W.A., and Porter, N.A. Suggested mechanisms for the production of 4-hydroxy-2-nonenal from the autoxidation of polyunsaturated fatty acids. Free Radic. Biol. Med. 8(6), 541-543 (1990).

2. Esterbauer, H., Schaur, R.J., and Zoliner, H. Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde, and related aldehydes. Free Radic. Biol. Med. 11(1), 81-128 (1991).

3. Sodum, R.S., and Chung, F.L. 1,N2-ethenodeoxyguanosine as a potential marker for DNA adduct formation by trans-4-hydroxy-2-nonenal. Cancer Res. 48(2), 320-323 (1988).

4. Schneider, C., Tallman, K.A., Porter, N.A., et al. Two distinct pathways of formation of 4-hydroxynonenal. Mechanisms of nonenzymatic transformation of the 9- and 13-hydroperoxides of linoleic acid to 4-hydroxyalkenals. The Journal of Biological Chemisty 276(24), 20831-20838 (2001).