A pro-inflammatory arachidonic acid metabolite
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14,15-Leukotriene D4

Item No. 10011361

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
S-[(1R,2E,4E,6Z,9Z)-13-carboxy-1-[(1S)-1-hydroxyhexyl]-2,4,6,9-tridecatetraen-1-yl]-L-cysteinyl-glycine
CAS Number
75290-64-1
Synonyms
  • Eoxin D4
  • EXD4
  • 14,15-LTD4
Molecular Formula
C25H40N2O6S
Formula Weight
496.7
Purity
≥97%
Formulation (Request formulation change)
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 1 mg/mlPBS (pH 7.2): >100 µg/ml
λmax
280 nm
SMILES
CCCCC[C@H](O)[C@H](SC[C@H](N)C(NCC(O)=O)=O)/C=C/C=C/C=C\C/C=C\CCCC(O)=O
InChi Code
InChI=1S/C25H40N2O6S/c1-2-3-12-15-21(28)22(34-19-20(26)25(33)27-18-24(31)32)16-13-10-8-6-4-5-7-9-11-14-17-23(29)30/h4,6-10,13,16,20-22,28H,2-3,5,11-12,14-15,17-19,26H2,1H3,(H,27,33)(H,29,30)(H,31,32)/b6-4-,9-7-,10-8+,16-13+/t20-,21-,22+/m0/s1
InChi Key
BUTLPEVGZIRJOA-SPCGXPCUSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    25 µg

    $140

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    50 µg

    $260

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    100 µg

    $492

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    Product Description

    14,15-Leukotriene D4 (14,15-LTD4) is a member of an alternate class of LTs synthesized by a pathway involving the dual actions of 15- and 12-lipoxygenases (15- and 12-LOs) on arachidonic acid via 15-HpETE and 14,15-LTA4 intermediates.1,2,3,4 14,15-LTD4 is classified as an eoxin (EXD4), because it is formed mostly by eosinophils.3 However, mast cells and nasal polyps can synthesize 14,15-LTD4 as well. Little is known about the physiological actions of 14,15-LTD4. It has weak contractile activity on both guinea pig ileum and pulmonary parenchyma in contrast to the effects of 5-LO-derived LTs.5,6 However, in an in vitro permeability assay, 14,15-LTD4 can increase vascular permeability of human endothelial cell monolayers, with similar potency to that of 5-LO-derived LTs, resulting in plasma leakage, a hallmark of inflammation.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. 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).

    3. 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).

    4. 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).

    5. Drazen, J.M., Lewis, R.A., Austen, K.F., et al. Contractile activities of structural analogs of leukotrienes C and D: Necessity of a hydrophobic region. Proc. Natl. Acad. Sci. USA 78(5), 3195-3198 (1987).

    6. Sala, A., Civelli, M., Oliva, D., et al. Contractile and binding activities of structural analogues of LTC4 in the longitudinal muscle of guinea-pig ileum. Eicosanoids 3(2), 105-110 (1990).

    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).