Hydroperoxide mixture derived from linoleic acid
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(±)13-HpODE

Item No. 10704

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(±)13-hydroperoxy-9Z,11E-octadecadienoic acid
CAS Number
23017-93-8
Molecular Formula
C18H32O4
Formula Weight
312.4
Purity
≥95%
Formulation (Request formulation change)
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): 1 mg/ml
SMILES
CCCCCC(OO)/C=C/C=C\CCCCCCCC(O)=O
InChi Code
InChI=1S/C18H32O4/c1-2-3-11-14-17(22-21)15-12-9-7-5-4-6-8-10-13-16-18(19)20/h7,9,12,15,17,21H,2-6,8,10-11,13-14,16H2,1H3,(H,19,20)/b9-7-,15-12+
InChi Key
JDSRHVWSAMTSSN-BSZOFBHHSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    50 µg

    $110

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    100 µg

    $209

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    500 µg

    $825

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    1 mg

    $1,100

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    Product Description

    (±)13-HpODE is a racemic mixture of hydroperoxides derived non-enzymatically from linoleic acid through the action of reactive oxygen species. Lipid hydroperoxides, including 13-HpODE, have limited direct biological actions, such as the activation of lipoxygenases.1 Normally, (±)13-HpODE is rapidly reduced to (±)13-HODE, a compound which exhibits many biological activities.2 Importantly, 13-HpODE can also be metabolized to unsaturated aldehydes that can, in turn, covalently bind to DNA, amino acids, and proteins.3,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jones, G.D., Russell, L., Darley-Usmar, V.M., et al. Role of lipid hydroperoxides in the activation of 15-lipoxygenase. Biochemistry 35, 7197-7203 (1996).

    2. Kühn, H. Biosynthesis, metabolization and biological importance of the primary 15-lipoxygenase metabolites 15-hydro(pero)xy-5Z,8Z,11Z,13E-eicosatetraenoic acid and 13-hydro(pero)xy-9Z,11E-octadecadienoic acid. Prog. Lipid Res. 35, 203-226 (1996).

    3. Williams, M.V., Wishnok, J.S., and Tannenbaum, S.R. Covalent adducts arising from the decomposition products lipid hydroperoxides in the presence of cytochrome C. Chem. Res. Toxicol. 20(5), 767-775 (2007).

    4. Iwahashi, H., Nishizaki, K., and Takagi, I. Cytochrome c catalyzes the formation of pentyl radical and octanoic acid radical from linoleic acid hydroperoxide. Biochem. J. 361, 57-66 (2002).

    5. Kawai, Y., Kato, Y., Fujii, H., et al. Immunochemical detection of a novel lysine adduct using an antibody to linoleic acid hydroperoxide-modifies protein. J. Lipid Res. 44, 1124-1131 (2003).

    Product Citations

    Wu, Z., Xiao, H., Rao, D., et al. Analytical strategy for oxylipin annotation by combining chemical derivatization-based retention index algorithm and feature tandem mass spectrometric fragmentation as a biomarker discovery tool. Anal. Chem. 95(43), 15933-15942 (2023).