A pro-inflammatory arachidonic acid metabolite
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

14,15-Leukotriene C4

Item No. 10011360

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
15S-hydroxy-14R-(S-glutathionyl)-5Z,8Z,10E,12E-eicosatetraenoic acid
CAS Number
75290-60-7
Synonyms
  • Eoxin C4
  • EXC4
  • 14,15-LTC4
Molecular Formula
C30H47N3O9S
Formula Weight
625.8
Purity
≥95%
Formulation (Request formulation change)
A 100 µg/ml solution in methanol
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](NC(CC[C@@H](C(O)=O)N)=O)C(NCC(O)=O)=O)/C=C/C=C/C=C\C/C=C\CCCC(O)=O
InChi Code
InChI=1S/C30H47N3O9S/c1-2-3-12-15-24(34)25(16-13-10-8-6-4-5-7-9-11-14-17-27(36)37)43-21-23(29(40)32-20-28(38)39)33-26(35)19-18-22(31)30(41)42/h4,6-10,13,16,22-25,34H,2-3,5,11-12,14-15,17-21,31H2,1H3,(H,32,40)(H,33,35)(H,36,37)(H,38,39)(H,41,42)/b6-4-
InChi Key
OBQVBASHEWLKCQ-JWVGDOKUSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    25 µg

    $140

    Add

    50 µg

    $260

    Add

    100 µg

    $492

    Add
    Lipid Resource Center
    Discover Products & Resources for Lipid Research
    • High-purity lipid standards
    • Lipid roles in biology
    • Lipids in health & disease
    • Lipids for pharmaceutical development
    • Protocols, advice, & resources
    EXPLORE NOW
    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-LTC4 is a member of 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 14,15-LTC4 is classified as an eoxin, because it is formed mostly by eosinophils.4 However, mast cells and nasal polyps can synthesize 14,15-LTC4 as well. Little is known about the physiological actions of 14,15-LTC4. It has weak contractile activity on both guinea pig ileum and pulmonary parenchyma in contrast to the effects of 5-LO-derived LTs.6,7 However, in an in vitro permeability assay, 14,15-LTC4 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.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).

    6. 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).

    7. 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).