An internal standard for the quantification of 4-oxo-2-nonenal
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Unlabeled Version(s)
101854-oxo-2-Nonenal
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4-oxo-2-Nonenal-d3

Item No. 10004174

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-oxo-2E-nonenal-d3
CAS Number
1313400-91-7
Synonyms
  • FAL 9:2;O-d3
  • 4-ONE-d3
Molecular Formula
C9H11D3O2
Formula Weight
157.2
Purity
≥99% deuterated forms (d1-d3)
Formulation
A 500 µg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 25 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): .5 mg/ml
λmax
223 nm
SMILES
CCCCCC(=O)/C=C\C=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+/i1D3
InChi Key
SEPPVOUBHWNCAW-PKJLGKQPSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    50 µg

    $106

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    100 µg

    $201

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    500 µg

    $834

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    1 mg

    $1,457

    Add
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    Product Description

    4-oxo-2-Nonenal-d3 (4-ONE-d3) contains three deuterium atoms at the terminal methyl position. It is intended for use as an internal standard for the quantification of 4-ONE (Item No. 10185) by GC- or LC-mass spectrometry (MS). 4-ONE 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-ONE 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-ONE also modifies 2'-deoxy guanosine, further implicating lipid peroxidation in mutagenesis and carcinogenesis.1

    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).