An internal standard for the quantification of leukotriene B4
Related Products
Alternative(s)
36097Leukotriene B4-d5
Unlabeled Version(s)
20110Leukotriene B4
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Leukotriene B4-d4

Item No. 320110

Technical Information
Formal Name
5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraenoic-6,7,14,15-d4 acid
CAS Number
124629-74-9
Synonyms
  • LTB4-d4
Molecular Formula
C20H28D4O4
Formula Weight
Purity
≥99% deuterated forms (d1-d4)
Formulation
A 100 µg/ml solution in acetonitrile
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlPBS pH 7.2: 1 mg/ml
λmax
270 nm
SMILES
CCCCC/C=C\C[C@@H](O)/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O
InChi Code
InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t18-,19-/m1/s1/i6D,9D,11D,15D
InChi Key
VNYSSYRCGWBHLG-PHKHWAPOSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    Product Description

    Leukotriene B4-d4 (LTB4-d4) is intended for use as an internal standard for the quantification of LTB4 (Item No. 20110) by GC- or LC-MS. LTB4 is a dihydroxy fatty acid derived from arachidonic acid through the 5-lipoxygenase pathway.1,2,3 It promotes a number of leukocyte functions including aggregation, stimulation of ion fluxes, enhancement of lysosomal enzyme release, superoxide anion production, chemotaxis, and chemokinesis. In subnanomolar ranges (3.9 x 10−10 M), LTB4 causes chemotaxis and chemokinesis in human PMNL.4 At higher concentrations, (1.0 x 10−7 M), LTB4 leads to neutrophil aggregation and degranulation as well as superoxide anion production.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rådmark, O., Malmsten, C., Samuelsson, B., et alLeukotriene A: Stereochemistry and enzymatic conversion to leukotriene B. Biochem. Biophys. Res. Commun. 92(3), 954-961 (1980).

    2. Ford-Hutchinson, A.W., Bray, M.A., Doig, M.V., et alLeukotriene B, a potent chemokinetic and aggregating substance released from polymorphonuclear leukocytes. Nature 286(5770), 264-265 (1980).

    3. McGee, J., and Fitzpatrick, F. Enzymatic hydration of leukotriene A4. Purification and characterization of a novel epoxide hydrolase from human erythrocytes. The Journal of Biological Chemisty 260(23), 12832-12837 (1985).

    4. Ford-Hutchinson, A.W. Leukotriene B4 in inflammation. Crit. Rev. Immunol. 10(1), 1-12 (1990).

    5. McMillan, R.M., and Foster, S.J. Leukotriene B4 and inflammatory disease. Agents Actions 24(1-2), 114-119 (1988).

    Product Citations

    Tufail, Y.Z., Guijas, C., Kummer, D.A., et alSuppression of pain transmission and behavior by inhibition of peripheral diacylglycerol metabolism. Cell Chem. Bio. 33(1), 74-90.e19 (2025).

    Wu, Z., Xiao, H., Rao, D., et alAnalytical strategy for oxylipin annotation by combining chemical derivatization-based retention index algorithm and feature tandem mass spectrometric fragmentation as a biomarker discovery tool. Anal. Chem. 95(43), 15933-15942 (2023).

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

    Sugimoto, S., Mena, H.A., Sansbury, B.E., et alBrown adipose tissue-derived MaR2 contributes to cold-induced resolution of inflammation. Nat. Metab. 4(6), 775-790 (2022).

    Laval, T., Pedró-Cos, L., Malaga, W., et alDe novo synthesized polyunsaturated fatty acids operate as both host immunomodulators and nutrients for Mycobacterium tuberculosis. eLife 10, e71946 (2021).

    Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et alLipid 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 alAnti-inflammatory and proresolving effects of the omega-6 polyunsaturated fatty acid adrenic acid. J. Immunol. 205(10), 2840-2849 (2020).

    Meriwether, D., Sulaiman, D., Volpe, C., et alApolipoprotein A-I mimetics mitigate intestinal inflammation in COX2-dependent inflammatory bowel disease model. J. Clin. Invest. 130, 3670-3685 (2019).

    Yan, B., Chu, H., Yang, D., et alCharacterization of the lipidomic profile of human coronavirus-infected cells: Implications for lipid metabolism remodeling upon coronavirus replication. Viruses 11(1), 73 (2019).

    Balas, L., Rise, P., Gandrath, D., et alProtectin D1 is rapidly metabolized by #-oxidation of its polar head chain. J. Med. Chem. (2019).

    Kutzner, L., Rund, K.M., Ostermann, A.I., et alDevelopment of an optimized LC-MS method for the detection of specialized pro-resolving mediators in biological samples. Front. Pharmacol. 10, 169 (2019).

    Naoe, S., Tsugawa, H., Takahashi, M., et alCharacterization of lipid profiles after dietary intake of polyunsaturated fatty acids using integrated untargeted and targeted lipidomics. Metabolites 9(10), 241 (2019).

    Dalli, J., Colas, R.A., Walker, M.E., et alLipid Mediator Metabolomics via LC-MS/MS Profiling and Analysis. Clinical Metabolomics 59-72 (2018).

    Lin, N., Shay, J.E.S., Xie, H., et alMyeloid cell hypoxia-inducible factors promote resolution of inflammation in experimental colitis. Front. Immunol. 9(2565), (2018).

    Archambault, A.-S., Turcotte, C., Martin, C., et alComparison of eight 15-lipoxygenase (LO) inhibitors on the biosynthesis of 15-LO metabolites by human neutrophils and eosinophils. PLoS One 13(8), e0202424 (2018).

    English, J.T., Norris, P.C., Hodges, R.R., et alIdentification and profiling of specialized pro-resolving mediators in human tears by lipid mediator metabolomics. Prostaglandins Leukot. Essent. Fatty Acids 117, 17-27 (2017).