An active metabolite of arachidonic acid
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15(S)-HETE

Item No. 34720

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
15S-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid
CAS Number
54845-95-3
Synonyms
  • 15(S)-Hydroxyeicosatetraenoic Acid
Molecular Formula
C20H32O3
Formula Weight
320.5
Purity
≥98%
Formulation (Request formulation change)
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
0.1 M Na2CO3: 2 mg/mlDMF: MiscibleDMSO: MiscibleEthanol: MisciblePBS (pH 7.2): 0.8 mg/ml
λmax
236 nm
SMILES
CCCCC[C@H](O)/C=C/C=C\C/C=C\C/C=C\CCCC(O)=O
InChi Code
InChI=1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14+/t19-/m0/s1
InChi Key
JSFATNQSLKRBCI-VAEKSGALSA-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

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    50 µg

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    100 µg

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    500 µg

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    Product Description

    15(S)-HETE is an active metabolite of arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607).1 It is formed via oxidation of arachidonic acid by 15-lipoxygenase 2 (15-LO-2) in macrophages, as well as the prostate, lung, and skin, but also by 15-LO-1 in airway epithelial cells, eosinophils, and reticulocytes.2,3 15(S)-HETE inhibits the proliferation of HT-29 colorectal and PC3 prostate cancer cells (IC50s = 40 and 30 µM, respectively).4,5 It increases kruppel-like factor 10 (KLF10) and decreases B cell lymphoma 2 (Bcl-2) protein levels in HT-29 cells when used at a concentration of 40 µM.4 15(S)-HETE (0.1 µM) increases HMG-CoA reductase protein levels in human dermal microvascular endothelial cells (HDMVECs).6 It increases Rac1 protein levels and induces farnesylation of Rac1 in HDMVECs when used at a concentration of 0.1 µM.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nadel, J.A., Conrad, D.J., Ueki, I.F., et al. Immunocytochemical localization of arachidonate 15-lipoxygenase in erythrocyes, leukocytes, and airway cells. J. Clin. Invest. 87(4), 1139-1145 (1991).

    2. Yuan, H., Li, M.-Y., Ma, L.T., et al. 15-Lipoxygenases and its metabolites 15(S)-HETE and 13(S)-HODE in the development of non-small cell lung cancer. Thorax. 65(4), 321-326 (2010).

    3. Powell, W.S., and Rokach, J. Biosynthesis, biological effects, and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid. Biochim. Biophys. Acta 1851(4), 340-355 (2014).

    4. Chen, G.G., Xu, H., Lee, J.F.Y., et al. 15-Hydroxy-eicosatetraenoic acid arrests growth of colorectal cancer cells via a peroxisome proliferator-activated receptor gamma-dependent pathway. Int. J. Cancer 107(5), 837-843 (2003).

    5. Shappell, S.B., Gupta, R.A., Manning, S., et al. 15S-hydroxyeicosatetraenoic acid activates peroxisome proliferator-activated receptor γ and inhibits proliferation in PC3 prostate carcinoma cells. Cancer Res. 61, 497-503 (2001).

    6. Singh, N.K., Kundumani-Sridharan, V., and Rao, G.N. 12/15-Lipoxygenase gene knockout severely impairs ischemia-induced angiogenesis due to lack of Rac1 farnesylation. Blood 118(20), 5701-5712 (2011).

    Product Citations

    Mainka, M., George, S., Angioni, C., et al. On the biosynthesis of specialized pro-resolving mediators in human neutrophils and the influence of cell integrit. Biochim. Biophys. Acta Mol. Cell Biol. Lipids 1867(3), 159093 (2022).

    Sun, W.-Y., Tyurin, V.A., Mikulska-Ruminska, K., et al. Phospholipase iPLA2β averts ferroptosis by eliminating a redox lipid death signal. Nat. Chem. Biol. (2021).

    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).

    Sasaki, A., Fukuda, H., Shiida, N., et al. Determination of ω-6 and ω-3 PUFA metabolites in human urine samples using UPLC/MS/MS. Anal. Bioanal. Chem. 407(6), 1625-1639 (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).

    Dobierzewska, A., Soman, S., Illanes, S.E., et al. Plasma cross-gestational sphingolipidomic analyses reveal potential first trimester biomarkers of preeclampsia. PLoS One 12(4), e0175118 (2017).

    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).

    Thollon, C., Iliou, J.P., Cambarrat, C., et al. Nature of the cardiomyocyte injury induced by lipid hydroperoxides. Cardiovasc. Res. 30, 648-655 (1995).

    Rao, C.V., Desai, D., Rivenson, A., et al. Chemoprevention of colon carcinogenesis by phenylethyl-3-methylcaffeate. Cancer Res. 55(11), 2310-2315 (1995).