A polyunsaturated keto acid that stimulates neutrophil migration
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Alternative(s)
260595-OxoETE methyl ester
Labeled Version(s)
3342505-OxoETE-d7
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5-OxoETE

Item No. 34250

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid
CAS Number
106154-18-1
Synonyms
  • 5-KETE
Molecular Formula
C20H30O3
Formula Weight
318.5
Purity
≥95%
Formulation
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: MiscibleDMSO: MiscibleEthanol: MisciblePBS pH 7.2: 0.8 mg/ml
λmax
279 nm
SMILES
CCCCC/C=C\C/C=C\C/C=C\C=C/C(=O)CCCC(=O)O
InChi Code
InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+
InChi Key
MEASLHGILYBXFO-XTDASVJISA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    25 µg

    $86

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    50 µg

    $163

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    100 µg

    $292

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    250 µg

    $687

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    Product Description

    5-OxoETE is a polyunsaturated keto acid formed by the oxidation of 5-HETE in human neutrophils by a specific dehydrogenase.1 It stimulates cytosolic calcium levels in neutrophils with an EC50 value of 2 nM.2 5-OxoETE selectively stimulates the migration and degranulation of eosinophils and activates the MAPK pathway in stimulated neutrophils via a specific G protein-coupled receptor.3,4,5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Powell, W.S., Gravelle, F., and Gravel, S. Metabolism of 5(S)-hydroxy-6,8,11,14-eicosatetraenoic acid and other 5(S)-hydroxyeicosanoids by a specific dehydrogenase in human polymorphonuclear leukocytes. The Journal of Biological Chemisty 267(27), 19233-19241 (1992).

    2. Powell, W.S., Zhang, Y., and Gravel, S. Effects of phorbol myristate acetate on the synthesis of 5-oxo-6,8,11,14-eicosatetraenoic acid by human polymorphonuclear leukocytes. Biochemistry 33(13), 3927-3933 (1994).

    3. O'Flaherty, J.T., Kuroki, M., Nixon, A.B., et al. 5-Oxo-eicosanoids and hematopoietic cytokines cooperate in stimulating neutrophil function and the mitogen-activated protein kinase pathway. The Journal of Biological Chemisty 271(30), 17821-17828 (1996).

    4. O'Flaherty, J.T., Kuroki, M., Nixon, A.B., et al. 5-Oxo-eicosatetraenoate is a broadly active, eosinophil-selective stimulus for human granulocytes. J. Immunol. 157(1), 336-342 (1996).

    5. Hosoi, T., Koguchi, Y., Sugikawa, E., et al. Identification of a novel human eicosanoid receptor coupled to Gi/o. The Journal of Biological Chemisty 277 (35), 31459-31465 (2002).

    6. Jones, C.E., Holden, S., Tenaillon, L., et al. Expression and characterization of a 5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid receptor highly expressed on human eosinophils and neutrophils. Mol. Pharmacol. 63(3), 471-477 (2003).

    Product Citations

    Pang, Y., Liu, X., Zhao, C., et al. LC-MS/MS-based arachidonic acid metabolomics in acute spinal cord injury reveals the upregulation of 5-LOX and COX-2 products. Free Radic. Biol. Med. 193(Pt 1), 363-372 (2022).

    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).

    Sorgi, C.A., Peti, A.P.F., Petta, T., et al. Comprehensive high-resolution multiple-reaction monitoring mass spectrometry for targeted eicosanoid assays. Sci. Data 5, 180167 (2018).