An internal standard for the quantification of 5-OxoETE
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Unlabeled Version(s)
342505-OxoETE
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5-OxoETE-d7

Item No. 334250

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic-6,8,9,11,12,14,15-d7 acid
CAS Number
1881277-29-7
Synonyms
  • 5-KETE-d7
Molecular Formula
C20H23D7O3
Formula Weight
325.5
Purity
≥99% deuterated forms (d1-d7)
Formulation
A 250 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([2H])=C([2H])\C/C([2H])=C([2H])\C/C([2H])=C([2H])\C=C([2H])\C(CCCC(O)=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+/i6D,7D,9D,10D,12D,13D,16D
InChi Key
MEASLHGILYBXFO-BWRCDNCFSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    25 µg

    $229

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    50 µg

    $431

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    100 µg

    $813

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    Product Description

    5-OxoETE-d7 contains seven deuterium atoms at the 6, 8, 9, 11, 12, 14, and 15 positions. It is intended for use as an internal standard for the quantification of 5-oxoETE by GC- or LC-mass spectrometry. 5-OxoETE is a polyunsaturated keto acid formed by the oxidation of 5-HETE in human neutrophils.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 mitogen-activated protein kinase (MAPK) pathway in stimulated neutrophils.3,4

    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-eicosatetraenoate is a broadly active, eosinophil-selective stimulus for human granulocytes. J. Immunol. 157(1), 336-342 (1996).

    4. 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).

    Product Citations

    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).