A stable form of LTA4
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Labeled Version(s)
10006197Leukotriene A4-d5 methyl ester
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Leukotriene A4 methyl ester

Item No. 20010

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5S-trans-5,6-oxido-7E,9E,11Z,14Z-eicosatetraenoic acid, methyl ester
CAS Number
73466-12-3
Synonyms
  • LTA4 methyl ester
Molecular Formula
C21H32O3
Formula Weight
332.5
Purity
≥97%
Formulation (Request formulation change)
A 100 µg/ml solution in hexane containing 1% triethylamine
Solubility(Learn about Variance in Solubility)
Acetone: >50 mg/mlDMF: >50 mg/mlDMSO: >50 mg/mlEthanol: >50 mg/mlPBS pH 7.2: insoluble and unstable.
λmax
279 nm
SMILES
CCCCC/C=C\C/C=C\C=C\C=C\[C@H](O1)[C@@H]1CCCC(OC)=O
InChi Code
InChI=1S/C21H32O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-16-19-20(24-19)17-15-18-21(22)23-2/h7-8,10-14,16,19-20H,3-6,9,15,17-18H2,1-2H3/b8-7-,11-10-,13-12+,16-14+/t19-,20-/m0/s1
InChi Key
WTKAVFHPLJFCMZ-NIBLXIPLSA-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

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    25 µg

    $159

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    50 µg

    $302

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    100 µg

    $571

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    Product Description

    Leukotriene A4 (LTA4) is synthesized in mast cells, eosinophils, and neutrophils from arachidonic acid by 5-lipoxygenase (5-LO), which exhibits both lipoxygenase and LTA4 synthase activities.1,2 LTA4 is rapidly metabolized by LTA4 hydrolase or LTC4 synthase to LTB4 or LTC4, respectively.2 LTA4, from leukocytes, is known to undergo transcellular metabolism in platelets, erythrocytes, and endothelial cells.3 Further metabolism of LTA4 by 15-LO leads to lipoxin biosynthesis.2 LTA4 as a free acid is highly unstable. The methyl ester is stable and can be readily hydrolyzed to the free acid as needed.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Shimizu, T., Rådmark, O., and Samuelsson, B. Enzyme with dual lipoxygenase activities catalyzes leukotriene A4 synthesis from arachidonic acid. Proc. Natl. Acad. Sci. USA 81, 689-693 (1984).

    2. Samuelsson, B., Dahlén, S.E., Lindgren, J.Å., et al. Leukotrienes and lipoxins: Structures, biosynthesis, and biological effects. Science 237(4819), 1171-1176 (1987).

    3. 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).

    Product Citations

    Van Anh, T.T., Mostafa, A., Rao, Z., et al. From Vietnamese plants to a biflavonoid that relieves inflammation by triggering the lipid mediator class switch to resolution. Acta Pharm. Sin. B. 11(6), 1629-1647 (2021).