A metabolite of 14,15-LTC4 with pro-inflammatory activity
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14,15-Leukotriene E4

Item No. 10011362

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
14R-[[(2R)-2-amino-2-carboxyethyl]thio]-15S-hydroxy-5Z,8Z,10E,12E-eicosatetraenoic acid
CAS Number
1000852-57-2
Synonyms
  • Eoxin E4
  • EXE4
  • 14,15-LTE4
Molecular Formula
C23H37NO5S
Formula Weight
439.6
Purity
≥97%
Formulation (Request formulation change)
A 100 µg/ml solution in methanol
Solubility(Learn about Variance in Solubility)
DMF: >50 mg/mlDMSO: >50 mg/mlEthanol: >50 mg/mlPBS (pH 7.2): >100 µg/ml
λmax
281 nm
SMILES
CCCCC[C@H](O)[C@H](SC[C@H](N)C(O)=O)/C=C/C=C/C=C\C/C=C\CCCC(O)=O
InChi Code
InChI=1S/C23H37NO5S/c1-2-3-12-15-20(25)21(30-18-19(24)23(28)29)16-13-10-8-6-4-5-7-9-11-14-17-22(26)27/h4,6-10,13,16,19-21,25H,2-3,5,11-12,14-15,17-18,24H2,1H3,(H,26,27)(H,28,29)/b6-4-,9-7-,10-8+,16-13+/t19?,20-,21+/m0/s1
InChi Key
JLJNENVYAVKECZ-RITCDKMASA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    25 µg

    $146

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    50 µg

    $274

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    100 µg

    $516

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    Product Description

    Leukotrienes (LTs) are a group of acute inflammatory mediators derived from arachidonic acid in leukocytes. The majority of these metabolites are formed through the 5-lipoxygenase (5-LO) pathway.1 14,15-Leukotriene E4 (14,15-LTE4) is a metabolite of 14,15-LTC4 and 14,15-LTD4, an alternate class of LTs synthesized by a pathway involving the dual actions of 15- and 12-LOs on arachidonic acid via 15-HpETE and 14,15-LTA4 intermediates.2,3,4,5 These metabolites are classified as eoxins because they are formed mostly by eosinophils.4 Mast cells and nasal polyps can synthesize 14,15-LTC4 as well, however metabolism to 14,15-LTE4 in these cells and tissue has not been documented. 14,15-LTE4 increases vascular permeability of human endothelial cell monolayers with about 10-fold less potency than LTC4, but approximately 100-fold greater potency than histamine.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Luo, M., Lee, S., and Brock, T.G. Leukotriene synthesis by epithelial cells. Histol. Histopathol. 18(2), 587-595 (2003).

    2. Yokoyama, C., Shinjo, F., Yoshimoto, T., et al. Arachidonate 12-lipoxygenase purified from porcine leukocytes by immunoaffinity chromatography and its reactivity with hydroperoxyeicosatetraenoic acids. The Journal of Biological Chemisty 261(35), 16714-16721 (1986).

    3. Bryant, R.W., Schewe, T., Rapoport, S.M., et al. Leukotriene formation by a purified reticulocyte lipoxygenase enzyme. Conversion of arachidonic acid and 15-hydroperoxyeicosatetraenoic acid to 14,15-leukotriene A4. The Journal of Biological Chemisty 260(6), 3548-3555 (1985).

    4. Feltenmark, S., Gautam, N., Brunnström, Å., et al. Eoxins are proinflammatory arachidonic acid metabolites produced via the 15-lipoxygenase-1 pathway in human eosinophils and mast cells. Proc. Natl. Acad. Sci. USA 105(2), 680-685 (2008).

    5. Sailesh, S., Kumar, Y.V.K., Prasad, M., et al. Sheep uterus dual lipoxygenase in the synthesis of 14,15-leukotrienes. Arch. Biochem. Biophys. 315(2), 362-368 (1994).

    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).