A monohydroxy fatty acid derived from linoleic acid
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(±)9-HODE

Item No. 38400

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(±)-9-hydroxy-10E,12Z-octadecadienoic acid
CAS Number
98524-19-7
Molecular Formula
C18H32O3
Formula Weight
296.5
Purity
≥98%
Formulation (Request formulation change)
A 1 mg/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=C\C=C/C(O)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+
InChi Key
NPDSHTNEKLQQIJ-ZJHFMPGASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    100 µg

    $160

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    500 µg

    $559

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    1 mg

    $1,038

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    Product Description

    (±)9-HODE is one of the two racemic monohydroxy fatty acids resulting from the non-enzymatic oxidation of linoleic acid. Approximately equal proportions of both isomers are found in mitochondrial and plasma membranes of rabbit reticulocytes.1,2 Oxidized LDL contains significant amounts of esterified 9- and 13-HpODEs and HODEs.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

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

    2. Kühn, H., Belkner, J., and Wiesner, R. Metabolism of polyenoic fatty acids by rabbit reticulocytes. Intracellular action of the erythroid lipoxygenase on membrane lipids. Biomedica Biochimica Acta 49, S25-S30 (1990).

    3. Folcik, V.A., and Cathcart, M.K. Predominance of esterified hydroperoxy-linoleic acid in human monocyte-oxidized LDL. J. Lipid Res. 35(9), 1570-1582 (1994).

    4. Ku, G., Thomas, C.E., Akeson, A.L., et al. Induction of interleukin 1β expression from human peripheral blood monocyte-derived macrophages by 9-hydroxyoctadecadienoic acid. The Journal of Biological Chemisty 267(20), 14183-14188 (1992).

    Product Citations

    Matsumoto, K., Takada, Y., Imamura, Y., et al. Live and heat-treated Lactiplantibacillus plantarum induce distinct metabolic and immune responses in intestinal epithelial cells. iScience 29(5), 115516 (2026).

    Yang, J., Yamashita-Kanemaru, Y., Morris, B.I., et al. Aspirin prevents metastasis by limiting platelet TXA2 suppression of T cell immunity. Nature (2025).

    Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. High levels of eicosanoids and docosanoids in the lungs of intubated COVID-19 patients. FASEB J. 35(6), e21666 (2021).

    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).

    Lahvic, J.L., Ammerman, M., Li, P., et al. Specific oxylipins enhance vertebrate hematopoiesis via the receptor GPR132. PNAS 115(37), 9252-9257 (2018).

    Kern, K., Schäfer, S.M.G., Cohnen, J., et al. The G2A receptor controls polarization of macrophage by determining their localization within the inflamed tissue. Front. Immunol. 9, 2261 (2018).

    Gouveia-Figueira, S., Karlsson, J., Deplano, A., et al. Characterisation of (R)-2-(2-fluorobiphenyl-4-yl)-N-(3-methylpyridin-2-yl)propanamide as a dual fatty acid amide hydrolase: Cyclooxygenase inhibitor. PLoS One 10(9), e0139212 (2015).

    Morgan, A.H., Hammond, V.J., Morgan, L., et al. Quantitative assays for esterified oxylipins generated by immune cells. Nat. Protoc. 5(12), 1919-1931 (2010).