An alkyne-tagged lipid peroxidation product
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 Alkyne

Item No. 17104

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-oxo-2E-Nonen-8-ynal
CAS Number
1680193-58-1
Synonyms
  • 4-ONE Alkyne
  • Alkynyl 4-oxo-2-Nonenal
  • Click Tag™ 4-oxo-2-Nonenal Alkyne
Molecular Formula
C9H10O2
Formula Weight
150.2
Purity
≥98%
Formulation (Request formulation change)
A 1 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/mlDMSO: 1 mg/mlEthanol: 10 mg/mlPBS (pH 7.2): 5 mg/ml
λmax
226 nm
SMILES
[H]C(/C=C/C(CCCC#C)=O)=O
InChi Code
InChI=1S/C9H10O2/c1-2-3-4-6-9(11)7-5-8-10/h1,5,7-8H,3-4,6H2/b7-5+
InChi Key
YSPMTKWXGONLQR-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

    100 µg

    $69

    Add

    500 µg

    $297

    Add

    1 mg

    $525

    Add

    5 mg

    $1,995

    Add
    Product Description

    4-oxo-2-Nonenal (4-ONE, Item No. 10185) is a product of lipid peroxidation that actively modifies histidine and lysine residues on proteins and causes protein cross-linking.1,2,3,4,5 It also modifies 2'-deoxyguanosine, further implicating lipid peroxidation in mutagenesis and carcinogenesis.1 4-ONE alkyne is an alkyne-tagged electrophile that can be used as a probe to isolate and identify the reaction products of lipid peroxidation using click chemistry.6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. 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).

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

    4. 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).

    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. Wang, C., Weerapana, E., Blewett, M.M., et al. A chemoproteomic platform to quantitatively map targets of lipid-derived electrophiles. Nat. Methods 11(1), 79-85 (2014).

    7. Beavers, W.N., Serwa, R., Shimozu, Y., et al. ω-Alkynyl lipid surrogates for polyunsaturated fatty acids: Free radical and enzymatic oxidations. J. Am. Chem. Soc. 136(32), 11529-11539 (2014).