The parent cysteinyl leukotriene produced by LTC4 synthase catalyzed conjugation of glutathione to LTA4
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Active Metabolite(s)
20310Leukotriene D4
Labeled Version(s)
10006198Leukotriene C4-d5
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Leukotriene C4

Item No. 20210

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5S-hydroxy-6R-(S-glutathionyl)-7E,9E,11Z,14Z-eicosatetraenoic acid
CAS Number
72025-60-6
Synonyms
  • LTC4
Molecular Formula
C30H47N3O9S
Formula Weight
625.8
Purity
≥95%
Formulation
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 1 mg/mlEthanol:H20 (95:5): 2 mg/mlPBS pH 7.2: 100 µg/ml
λmax
280 nm
SMILES
CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](NC(CC[C@H](N)C(O)=O)=O)C(NCC(O)=O)=O)[C@@H](O)CCCC(O)=O
InChi Code
InChI=1S/C30H47N3O9S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-25(24(34)15-14-17-27(36)37)43-21-23(29(40)32-20-28(38)39)33-26(35)19-18-22(31)30(41)42/h6-7,9-13,16,22-25,34H,2-5,8,14-15,17-21,31H2,1H3,(H,32,40)(H,33,35)(H,36,37)(H,38,39)(H,41,42)/b7-6-,10-9-,12-11+,16-13+/t22-,23-,24-,25+/m0/s1
InChi Key
GWNVDXQDILPJIG-MOKORLJISA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    25 µg

    $171

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    50 µg

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    100 µg

    $580

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    Product Description

    Leukotriene C4 (LTC4) is the parent cysteinyl leukotriene produced by the LTC4 synthase catalyzed conjugation of glutathione to LTA4. LTC4 is produced by neutrophils, macrophages, mast cells, and by transcellular metabolism in platelets.1 It is one of the constituents of slow-reacting substance of anaphylaxis (SRS-A) and exhibits potent smooth muscle contracting activity.2 LTC4-induced bronchoconstriction and enhanced vascular permeability contribute to the pathogenesis of asthma and acute allergic hypersensitivity.3,4 The concentration of LTC4 required to produce marked contractions of lung parenchymal strips and isolated tracheal rings is about 1 nM.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Maclouf, J.A., and Murphy, R.C. Transcellular metabolism of neutrophil-derived leukotriene A4 by human platelets. A potential cellular source of leukotriene C4. The Journal of Biological Chemisty 263(1), 174-181 (1988).

    2. Piper, P.J. Formation and actions of leukotrienes. Physiol. Rev. 64(2), 744-761 (1984).

    3. Samuelsson, B. Leukotrienes: Mediators of immediate hypersensitivity reactions and inflammation. Science 220(4597), 568-575 (1983).

    4. Lefer, A.M. Leukotrienes as mediators of ischemia and shock. Biochem. Pharmacol. 35(2), 123-127 (1986).

    Product Citations

    Archambault, A.-S., Brassard, J., Bernatchez, É., et al. Human and mouse eosinophils differ in their ability to biosynthesize eicosanoids, docosanoids, the endocannabinoid 2-arachidonoyl-glycerol and its congeners. Cells 11(1), 141 (2022).

    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).

    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).

    Lu, E., Wolfreys, F.D., Muppidi, J.R., et al. S-Geranylgeranyl-L-glutathione is a ligand for human B cell-confinement receptor P2RY8. Nature 567(7724), 244-248 (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).

    Ono, E., Mita, H., Taniguchi, M., et al. Concentration of 14,15-leukotriene C4 (eoxin C4) in bronchoalveolar lavage fluid. Clin. Exp. Allergy (2009).

    Thompson, C., Cloutier, A., Bossé, Y., et al. Signaling by the cysteinyl-leukotriene receptor 2. Involvement in chemokine gene transcription. The Journal of Biological Chemisty 283(4), 1974-1984 (2008).