A natural metabolite of LTB4
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12-oxo Leukotriene B4

Item No. 20140

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5S-hydroxy-12-oxo-6Z,8E,10E,14Z-eicosatetraenoic acid
CAS Number
136696-10-1
Synonyms
  • 12-keto LTB4
  • 12-oxo LTB4
Molecular Formula
C20H30O4
Formula Weight
334.4
Purity
≥90%
Formulation (Request formulation change)
A 100 µg/ml solution in acetonitrile
Solubility(Learn about Variance in Solubility)
DMF: MiscibleDMSO: MiscibleEthanol: MisciblePBS (pH 7.2): > 1 mg/ml
λmax
314 nm
SMILES
CCCCC/C=C\CC(=O)\C=C/C=C\C=C\[C@@H](O)CCCC(=O)O
InChi Code
InChI=1S/C20H30O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,19,22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t19-/m1/s1
InChi Key
SJVWVCVZWMJXOK-NOJHDUNKSA-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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    10 µg

    $117

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    25 µg

    $245

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    50 µg

    $456

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    100 µg

    $796

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    Product Description

    12-oxo LTB4 is an initial metabolite of LTB4 formed via the LTB4 12-hydroxydehydrogenase pathway.1,2,3 It is rapidly converted to 10,11-dihydro-12-oxo-LTB4, followed by reduction of the 12-oxo group to give 10,11-dihydro-LTB4.2 12-oxo-LTB4 (EC50 = 33 nM) is about 70-fold less potent than LTB4 (EC50 = 0.46 nM) at stimulating Ca2+ mobilization in human neutrophils.4 It is also significantly less potent than LTB4 at stimulating neutrophil migration with EC50 values of 170 and 2.7 nM for 12-oxo-LTB4 and LTB4, respectively.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yokomizo, T., Izumi, T., Takahashi, T., et al. Enzymatic inactivation of leukotriene B4 by a novel enzyme found in the porcine kidney. Purification and properties of leukotriene B4 12-hydroxydehydrogenase. The Journal of Biological Chemisty 268, 18128-18135 (1993).

    2. Wainwright, S.L., and Powell, W.S. Mechanism for the formation of dihydro metabolites of 12-hydroxyeicosanoids conversion of leukotriene B4 and 12-hydroxy-5,8,10,14-eicosatetraenoic acid to 12-oxo intermediates. The Journal of Biological Chemisty 266(31), 20899-20906 (1991).

    3. Wheelan, P., Zirrolli, J.A., Morelli, J.G., et al. Metabolism of leukotriene B4 by cultural human keratinocytes. Formation of glutathione conjugates and dihydro metabolites. The Journal of Biological Chemisty 268, 25439-25448 (1993).

    4. Powell, W.S., Rokach, J., Khanapure, S.P., et al. Effects of metabolites of leukotriene B4 on human neutrophil migration and cytosolic calcium levels. J. Pharmacol. Exp. Ther. 276(2), 728-736 (1996).

    Product Citations

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

    Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. Lipid storm within the lungs of severe COVID-19 patients: Extensive levels of cyclooxygenase and lipoxygenase-derived inflammatory metabolites. medRxiv (2020).