Product of 15-LO metabolism of linoleic acid
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13(S)-HODE

Item No. 38610

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
13S-hydroxy-9Z,11E-octadecadienoic acid
CAS Number
29623-28-7
Molecular Formula
C18H32O3
Formula Weight
296.5
Purity
≥98%
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
λmax
234 nm
SMILES
CCCCC[C@H](O)/C=C/C=C\CCCCCCCC(O)=O
InChi Code
InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15,17,19H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)/b9-7-,15-12+/t17-/m0/s1
InChi Key
HNICUWMFWZBIFP-IRQZEAMPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    25 µg

    $69

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    50 µg

    $103

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    100 µg

    $150

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    250 µg

    $341

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    Product Description

    13(S)-HODE is produced by incubation of linoleic acid with plant and mammalian lipoxygenases. It has been shown to inhibit the adhesion of tumor cells to the endothelium at concentrations around 1 µM,1,2 and down regulates the expression of the IRGpIIb/IIIa receptor.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Buchanan, M.R., Haas, T.A., Lagarde, M., et al. 13-Hydroxyoctadecadienoic acid is the vessel wall chemorepellant factor, LOX. The Journal of Biological Chemisty 260(30), 16056-16059 (1985).

    2. Honn, K.V., Nelson, K.K., Renaud, C., et al. Fatty acid modulation of tumor cell adhesion to microvessel endothelium and experimental metastasis. Prostaglandins 44(5), 413-429 (1992).

    3. Grossi, I.M., Fitzgerald, L.A., Umbarger, L.A., et al. Bidirectional control of membrane expression and/or activation of the tumor cell IRGpIIb/IIIa receptor and tumor cell adhesion by lipoxygenase products of arachidonic acid and linoleic acid. Cancer Res. 49(4), 1029-1037 (1989).

    Product Citations

    Liu, F., Zuo, X., Liu, Y., et al. Suppression of membranous LRP5 recyling, Wnt/β-catenin signaling, and colon carcinogenesis by 15-LOX-1 peroxidation of linoleic acid in PI3P. Cell Rep. 32(7), 108049 (2020).

    Meriwether, D., Sulaiman, D., Volpe, C., et al. Apolipoprotein A-I mimetics mitigate intestinal inflammation in COX2-dependent inflammatory bowel disease model. J. Clin. Invest. 130, 3670-3685 (2019).

    Banthiya, S., Kalms, J., Yoga, E.G., et al. Structural and functional basis of phospholipid oxygenase activity of bacterial lipoxygenase from Pseudomonas aeruginosa. Biochim. Biophys. Acta 1861, 1681-1692 (2016).