An active metabolite of LTC4 and a constituent of SRS-A
Related Products
Labeled Version(s)
10006199Leukotriene D4-d5
Parent Compound(s)
20210Leukotriene C4
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Leukotriene D4

Item No. 20310

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5S-hydroxy-6R-(S-cysteinylglycinyl)-7E,9E,11Z,14Z-eicosatetraenoic acid
CAS Number
73836-78-9
Synonyms
  • 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=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N)C(NCC(O)=O)=O)[C@@H](O)CCCC(O)=O
InChi Code
InChI=1S/C25H40N2O6S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-22(21(28)15-14-17-23(29)30)34-19-20(26)25(33)27-18-24(31)32/h6-7,9-13,16,20-22,28H,2-5,8,14-15,17-19,26H2,1H3,(H,27,33)(H,29,30)(H,31,32)/b7-6-,10-9-,12-11+,16-13+/t20-,21-,22+/m0/s1
InChi Key
YEESKJGWJFYOOK-IJHYULJSSA-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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    100 µg

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    Product Description

    Leukotriene D4 (LTD4) is an active metabolite of LTC4 (Item No. 20210) and a constituent of slow-reacting substance of anaphylaxis (SRS-A).1,2 It is formed via metabolism of LTC4 by γ-glutamyl transpeptidase. Like LTC4, LTD4 (0.01-0.1 pM) induces contractions in isolated guinea pig parenchymal strips and tracheal spirals.3 In vivo, LTD4 increases insufflation pressure, a marker of bronchoconstriction, in anesthetized guinea pigs by 100% when administered at a dose of 89 pmol per animal.4 It also increases vascular permeability in guinea pig skin when administered intradermally at a dose of 0.1 pmol per animal.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Örning, L., Hammarström, S., and Samuelsson, B. Leukotriene D: A slow reacting substance from rat basophilic leukemia cells. Proc. Natl. Acad. Sci. USA 77(4), 2014-2017 (1980).

    2. Hammarström, S., Örning, L., and Bernström, K. Metabolism of leukotrienes. Mol. Cell Biochem. 69(1), 7-16 (1985).

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

    4. Hedqvist, P., Dahlén, S.E., Gustafsson, L., et al. Biological profile of leukotrienes C4 and D4. Acta Physiol. Scand. 110(3), 331-333 (1980).

    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).

    Ceraudo, E., Horioka, M., Mattheisen, J.M., et al. Direct evidence that the GPCR CysLTR2 mutant causative of uveal melanoma is constitutively active with highly biased signaling. The Journal of Biological Chemisty 296, 100163 (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).

    Brouwers, H., Jónasdóttir, H.S., Kuipers, M.E., et al. Anti-inflammatory and proresolving effects of the omega-6 polyunsaturated fatty acid adrenic acid. J. Immunol. 205(10), 2840-2849 (2020).

    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).

    Ni, N.C., Yan, D., Ballantyne, L.L., et al. A selective cysteinyl leukotriene receptor 2 antagonist blocks myocardial ischemia/reperfusion injury and vascular permeability in mice. J. Pharmacol. Exp. Ther. 339(3), 768-778 (2011).

    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).

    Sasaki, A., Fukuda, H., Shiida, N., et al. Determination of ω-6 and ω-3 PUFA metabolites in human urine samples using UPLC/MS/MS. Anal. Bioanal. Chem. 407(6), 1625-1639 (2015).

    Qi, H.-Y., Daniels, M.P., Liu, Y., et al. A cytosolic phospholipase A2-initiated lipid mediator pathway induces autophagy in macrophages. J. Immunol. 187(10), 5286-5292 (2011).

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

    Medina, P.P., and Sanchez-Cespedes, M. Involvement of the chromatin-remodeling factor BRG1/SMARCA4 in human cancer. Epigenetics 3(2), 64-68 (2008).

    Gronert, K., Martinsson-Niskanen, T., Ravasi, S., et al. Selectivity of recombinant human leukotriene D4, leukotriene B4, and lipoxin A4 receptors with aspirin-triggered 15-epi-LXA4 and regulation of vascular and inflammatory responses. Am. J. Pathol. 158(1), 3-9 (2001).