Stimulates EGF-dependent mitogenesis and tyrosine phosphorylation
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13(S)-HpODE

Item No. 48610

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
13S-hydroperoxy-9Z,11E-octadecadienoic acid
CAS Number
33964-75-9
Molecular Formula
C18H32O4
Formula Weight
312.4
Purity
≥95%
Formulation (Request formulation change)
A 500 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
λmax
234 nm
SMILES
CCCCC[C@H](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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    50 µg

    $72

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    100 µg

    $134

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    500 µg

    $627

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    1 mg

    $1,042

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    Product Description

    13(S)-HpODE is produced by the oxidation of linoleic acid by lipoxygenase-1 (LO-1) in many plants including soybean, flaxseed, apples, and tea leaves,1,2 and by 15-LO in mammals.3 In plants, 13(S)-HpODE is the preferred substrate for the garlic bulb divinyl ether synthase.4 In mammalian tissues, 13(S)-HpODE is generally reduced to 13(S)-HODE (Catalog No. 38610), a compound which exhibits many biological activities.3 A direct action for 13(S)-HpODE has been demonstrated in Syrian hamster embryo cells where it stimulates EGF-dependent mitogenesis and up-regulation of EGF-dependent tyrosine phosphorylation.5 Membrane-esterified 13(S)-HpODE has been identified in human atherosclerotic plaques.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gardner, H.W. Soybean lipoxygenase-1 enzymically forms both (9S)- and (13S)-hydroperoxides from linoleic acid by a pH-dependent mechanism. Biochim. Biophys. Acta 1001(3), 274-281 (1989).

    2. Vick, B.A. Oxygenated fatty acids of the lipoxygenase pathway. Lipid Metabolism in Plants 167-191 (1993).

    3. 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).

    4. Grechkin, A.N., and Hamberg, M. Divinyl ether synthase from garlic (Allium sativum L.) bulbs: Sub-cellular localization and substrate regio- and stereospecificity. FEBS Lett. 388, 112-114 (1996).

    5. Glasgow, W.C., Hui, R., Everhart, A.L., et al. The linoleic acid metabolite, (13S)-hydroperoxyoctadecadienoic acid, augments the epidermal growth factor receptor signaling pathway by attenuation of receptor dephosphorylation. Differential response in Syrian hamster embryo tumor suppressor phenotypes. The Journal of Biological Chemisty 272, 19269-19276 (1997).

    6. Folcik, V.A., Nivar-Aristy, R.A., Krajewski, L.P., et al. Lipoxygenase contributes to the oxidation of lipids in human atherosclerotic plaques. J. Clin. Invest. 96, 504-510 (1995).

    Product Citations

    Ricotta, M., Iannuzzi, M., De Vivo, G., et al. Physio-pathological roles of transglutaminase-catalyzed reactions. World J. Biol. Chem. 1(5), 181-187 (2010).

    Lee, S., Park, Y., Kim, J., et al. A fluorescence-based assay for measuring the redox potential of 5-lipoxygenase inhibitors. PLoS One 9(2), e87708 (2014).