A lipid peroxidation product
Related Products
Labeled Version(s)
100041744-oxo-2-Nonenal-d3
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

4-oxo-2-Nonenal

Item No. 10185

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-oxo-2E-nonenal
CAS Number
103560-62-9
Synonyms
  • FAL 9:2;O
  • 4-ONE
Molecular Formula
C9H14O2
Formula Weight
154.2
Purity
≥98%
Formulation (Request formulation change)
A 5 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): 0.5 mg/ml
SMILES
CCCCCC(/C=C/C=O)=O
InChi Code
InChI=1S/C9H14O2/c1-2-3-4-6-9(11)7-5-8-10/h5,7-8H,2-4,6H2,1H3/b7-5+
InChi Key
SEPPVOUBHWNCAW-FNORWQNLSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    500 µg

    $72

    Add

    1 mg

    $137

    Add

    5 mg

    $537

    Add

    10 mg

    $930

    Add
    Lipid Resource Center
    Discover Products & Resources for Lipid Research
    • High-purity lipid standards
    • Lipid roles in biology
    • Lipids in health & disease
    • Lipids for pharmaceutical development
    • Protocols, advice, & resources
    EXPLORE NOW
    Product Description

    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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description 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. 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).

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

    7. 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).

    8. 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).