An internal standard for the quantification of leukotriene A4 methyl ester
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Unlabeled Version(s)
20010Leukotriene A4 methyl ester
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Leukotriene A4-d5 methyl ester

Item No. 10006197

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5S-trans-5,6-oxido-7E,9E,11Z,14Z-eicosatetraenoic-19,19,20,20, and 20-d5 acid, methyl ester
Synonyms
  • LTA4-d5 methyl ester
Molecular Formula
C21H27D5O3
Formula Weight
337.5
Purity
≥99% deuterated forms (d1-d5)
Formulation
A 100 µg/ml solution in hexane containing 1% triethylamine
Solubility(Learn about Variance in Solubility)
Acetone: >50 µg/mlDMF: >50 µg/mlDMSO: >50 µg/mlEthanol: >50 µg/mlPBS (pH 7.2): Insoluble & unstable
λmax
279 nm
SMILES
[2H]C([2H])([2H])C([2H])([2H])CCC/C=C\C/C=C\C=C\C=C\[C@H]1[C@@H](O1)CCCC(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/i1D3,3D2
InChi Key
WTKAVFHPLJFCMZ-RIVYOXCQSA-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

    $321

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    50 µg

    $609

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    100 µg

    $1,088

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    Product Description

    Leukotriene A4-d5 (LTA4-d5) methyl ester contains four deuterium atoms at the 19, 19', 20, 20, and 20 positions. It is intended for use as an internal standard for the quantification of LTA4 methyl ester by GC- or LC-mass spectrometry. 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).