A metabolite of linoleic acid
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9(S)-HODE

Item No. 38410

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9S-hydroxy-10E,12Z-octadecadienoic acid
CAS Number
73543-67-6
Synonyms
  • α-Dimorphecolic Acid
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
OC(CCCCCCC[C@H](O)/C=C/C=C\CCCCC)=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-/m1/s1
InChi Key
NPDSHTNEKLQQIJ-UINYOVNOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    100 µg

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    Product Description

    9(S)-HODE is a metabolite of the ω-6 polyunsaturated fatty acid linoleic acid (Item Nos. 90150 | 90150.1 | 21909).1,2 It is formed from linoleic acid by lipoxygenases. 9(S)-HODE (68 µM) increases transactivation of peroxisome proliferator-activated receptor α (PPARα) and PPARγ in reporter assays using mouse aortic endothelial cells.3 It induces chemotaxis of primary human monocytes when used at a concentration of 10 µM.4 9(S)-HODE has been found in oxidized LDL (oxLDL).5

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

    3. Hourton, D., Delerive, P., Stanková, J., et al. Oxidized low-density lipoprotein and peroxisome-proliferator-activated receptor α down-regulate platelet-activating-factor receptor expression in human macrophages. Biochem. J. 354(Pt 1), 225-232 (2001).

    4. 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).

    5. 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

    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).