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Structure Database (LMSD)

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Common Name

4-oxo-nonenal

Systematic Name

4-oxo-2E-nonenal

Synonyms

4-ONE

LM ID

LMFA06000254

Formula

C₉H₁₄O₂

Exact Mass

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154.09938

Sum Composition

FAL 9:2;O

Status

Curated

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Classification

Biological Context

4-hydroxy Nonenal is a lipid peroxidation product derived from oxidized ω-6 polyunsaturated fatty acids such as arachidonic acid and linoleic acid.^1,2 It exhibits various biological activities such as cytotoxicity, growth inhibiting activity, genotoxicity, and chemotactic activity and has been widely used as a marker of lipid peroxidation.^1,2,3 4-oxo-2-Nonenal is a more recently identified product of lipid peroxidation.^4,5,6 It actively modifies histidine and lysine residues on proteins and causes protein cross-linking.^7,8 4-oxo-2-Nonenal also modifies 2'-deoxyguanosine, further implicating lipid peroxidation in mutagenesis and carcinogenesis.⁴

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. Rindgen, D., Nakajima, M., Wehrli, S., et al. Covalent modifications to 2'-deoxyguanosine by 4-oxo-nonenal, a novel product of lipid peroxidation. Chem. Res. Toxicol. 12(12), 1195-1204 (1999).

5. Zhang, W.H., Liu, J., Xu, G., et al. Model studies on protein side chain modification by 4-oxo-2-nonenal. Chem. Res. Toxicol. 16(4), 512-523 (2003).

6. Liu, Z., Minkler, P.E., and Sayre, L.M. Mass spectroscopic characterization of protein modification by 4-hydroxy-2-(E)-nonenal and 4-oxo-2-(E)-nonenal. Chem. Res. Toxicol. 16(7), 901-911 (2003).

7. Spiteller, P., Kern, W., Reiner, J., et al. Aldehydic lipid peroxidation products derived from linoleic acid. Biochim. Biophys. Acta 1531(3), 188-208 (2001).

8. Lee, S.H., and Blair, I.A. Characterization of 4-oxo-2-nonenal as a novel product of lipid peroxidation. Chem. Res. Toxicol. 13(8), 698-702 (2000).