A leukotriene
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Leukotriene B5

Item No. 21110

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5S,12R-dihydroxy-6Z,8E,10E,14Z,17Z-eicosapentaenoic acid
CAS Number
80445-66-5
Synonyms
  • LTB5
Molecular Formula
C20H30O4
Formula Weight
334.5
Purity
≥98%
Formulation
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: >50 mg/mlDMSO: >50 mg/mlEthanol: >50 mg/mlPBS pH 7.2: >1 mg/ml
λmax
271 nm
SMILES
CC/C=C\C/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(O)=O
InChi Code
InChI=1S/C20H30O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h3-4,6-11,14-15,18-19,21-22H,2,5,12-13,16-17H2,1H3,(H,23,24)/b4-3-,8-7+,9-6-,14-10+,15-11-/t18-,19-/m1/s1
InChi Key
BISQPGCQOHLHQK-HDNPQISLSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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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.

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    25 µg

    $153

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    50 µg

    $291

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    100 µg

    $550

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    500 µg

    $2,141

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    Product Description

    Leukotriene B5 (LTB5) is a leukotriene with diverse biological activities.1,2,3,4,5 It is a metabolite of eicosapentaenoic acid (EPA; Item Nos. 90110 | 90110.1 | 21908) formed through the 5-lipoxygenase (5-LO) pathway.6 LTB5 increases contraction of bullfrog lung strips ex vivo in a concentration-dependent manner.1 In vivo, LTB5 (100 nM) reduces tumor volume in mice injected with Tm1 murine melanoma cells.2 LTB5 also elicits chemokinesis and lysosomal enzyme release from polymorphonuclear leukocytes (PMNLs) 20- to 30-fold less, and induces platelet aggregation 8-fold less, potently than LTB4 (Item No. 20110).3,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Andazola, J.J., Underwood, J.A., Chiono, M., et al. Leukotriene B4 and leukotriene B5 have binding sites on lung membranes and cause contraction of bullfrog lung. J. Pharmacol. Exp. Ther. 263(3), 1111-1117 (1992).

    2. Bachi, A.L., Kim, F.J., Nonogaki, S., et al. Leukotriene B4 creates a favorable microenvironment for murine melanoma growth. Mol. Cancer Res. 7(9), 1417-1424 (2009).

    3. Lee, T.H., Mencia-Huerta, J.M., Shih, C., et al. Characterization and biologic properties of 5,12-dihydroxy derivatives of eicosapentaenoic acid, including leukotriene B5 and the double lipoxygenase product. The Journal of Biological Chemisty 259(4), 2383-2389 (1984).

    4. Leitch, A.G., Lee, T.H., Ringel, E.W., et al. Immunologically induced generation of tetraene and pentaene leukotrienes in the peritoneal cavities of Menhaden-fed rats. J. Immunol. 132(5), 2559-2565 (1984).

    5. Terano, T., Salmon, J.A., and Moncada, S. Biosynthesis and biological activity of leukotriene B5. Prostaglandins 27(2), 217-232 (1984).

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

    Hartling, I., Cremonesi, A., Osuna, E., et al. Quantitative profiling of inflammatory and pro-resolving lipid mediators in human adolescents and mouse plasma using UHPLC-MS/MS. Clin. Chem. Lab. Med. 59(11), 1811-1823 (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).