A linoleic acid metabolite
Related Products
Enantiomer(s)
384109(S)-HODE
Isomer(s)
38400(±)9-HODE
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9(R)-HODE

Item No. 38405

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9R-hydroxy-10E,12Z-octadecadienoic acid
CAS Number
10075-11-3
Synonyms
  • 9(R)-Hydroxyoctadecadienoic Acid
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
O[C@@H](/C=C/C=C\CCCCC)CCCCCCCC(O)=O
InChi Code
InChI=1S/C18H32O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14,17,19H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6-,14-11+/t17-/m0/s1
InChi Key
NPDSHTNEKLQQIJ-WXUVIADPSA-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

    $90

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    50 µg

    $168

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    100 µg

    $280

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    250 µg

    $653

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    Product Description

    9(R)-HODE is a monohydroxy fatty acid and metabolite of linoleic acid (Item Nos. 90150 | 90150.1 | 21909).1,2 It is formed from linoleic acid by COX and lipoxygenase (LO).3,4 9(R)-HODE induces chemotaxis, increases the levels of chemokine (C-C motif) receptor 9 (CCR9) and chemokine (C-X-C motif) receptor 4 (CXCR4), and inhibits IL-6 release in primary human monocytes.5 It inhibits CD3α- and CD28-induced proliferation of isolated human peripheral blood lymphocytes when used at a concentration of 25 µg/ml.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Baer, A.N., Costello, P.B., and Green, F.A. Stereospecificity of the hydroxyeicosatetraenoic and hydroxyoctadecadienoic acids produced by cultured bovine endothelial cells. Biochim. Biophys. Acta 1085(1), 45-52 (1991).

    2. Camacho, M., Godessart, N., Anton, R., et al. Interleukin-1 enhances the ability of cultured human umbilical vein endothelial cells to oxidize linoleic acid. The Journal of Biological Chemisty 270(29), 17279-17286 (1995).

    3. Hamberg, M. Stereochemistry of oxygenation of linoleic acid catalyzed by prostaglandin-endoperoxide H synthase-2. Arch. Biochem. Biophys. 349(2), 376-380 (1998).

    4. Kühn, H., Belkner, J., and Wiesner, R. Subcellular distribution of lipoxygenase products in rabbit reticulocyte membranes. Eur. J. Biochem. 191(1), 221-227 (1990).

    5. Rolin, J., Vego, H., and Maghazachi, A.A. Oxidized lipids and lysophosphatidylcholine induce the chemotaxis, up-regulate the expression of CCR9 and CXCR4 and abrogate the release of IL-6 in human monocytes. Toxins (Basel) 6(9), 2840-2856 (2014).

    6. Wefers, C., Duiveman-de Boer, T., Zusterzeel, P.L.M., et al. Different lipid regulation in ovarian cancer: Inhibition of the immune system. Int. J. Mol. Sci. 19(1), 273 (2018).