A theoretical 5-LO metabolite of arachidonoyl ethanolamide
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Leukotriene B4 Ethanolamide

Item No. 20112

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2-hydroxyethyl)-5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraenamide
CAS Number
877459-63-7
Synonyms
  • LTB4-EA
Molecular Formula
C22H37NO4
Formula Weight
379.5
Purity
≥97%
Formulation
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 100 mg/mlDMSO: 100 mg/mlEthanol: 100 mg/mlPBS (pH 7.2): 12 mg/ml
λmax
270 nm
SMILES
CCCCC/C=C\C[C@@H](O)/C=C/C=C\C=C\[C@@H](O)CCCC(=O)NCCO
InChi Code
InChI=1S/C22H37NO4/c1-2-3-4-5-6-9-13-20(25)14-10-7-8-11-15-21(26)16-12-17-22(27)23-18-19-24/h6-11,14-15,20-21,24-26H,2-5,12-13,16-19H2,1H3,(H,23,27)/b8-7+,9-6-,14-10+,15-11-/t20-,21-/m1/s1
InChi Key
DQLVVNIINUTUIU-XLFGVTECSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

    $165

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    50 µg

    $289

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    100 µg

    $543

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    Product Description

    The effects of Leukotriene B4 (LTB4) are mediated by two known receptors, BLT1 and BLT2.1,2 LTB4 is a high affinity ligand for BLT1, and many of its pro-inflammatory effects are believed to be transduced through this receptor. The BLT2 is more enigmatic, in that LTB4 is not a high-affinity ligand, nor is it clear that BLT2 activation promotes inflammation. LTB4 ethanolamide (LTB4-EA) is a theoretical 5-LO metabolite of arachidonoyl ethanolamide (AEA). In CHO cells transfected with human BLTR1, LTB4-EA was a potent antagonist with about three times greater affinity for the receptor than LTB4 (Ki = 1.22 nM versus 3.88 nM). LTB4-EA antagonizes the LTB4-induced contractions of guinea pig lung parenchyma with an EC50 of 10 nM.3 LTB4-EA thus represents a potential endogenous anti-inflammatory compound functioning as a natural antagonist of BLTR1.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yokomizo, T., Izumi, T., Chang, K., et al. A G-protein-coupled receptor for leukotriene B4 that mediates chemotaxis. Nature 387(6633), 620-624 (1997).

    2. Yokomizo, T., Kato, K., Terawaki, K., et al. A second leukotriene B4 receptor, BLT2: A new therapeutic target in inflammation and immunological disorders. J. Exp. Med. 193(3), 421-431 (2000).

    3. McHugh, D., McMaster, S., and Ross, R. Pharmacological characterization of LTB4 ethanolamide: Interaction with leukotriene (BLT) and vanilloid (TRPV1) receptors. 121-121.