An internal standard for the quantification of Lipoxin A4
Related Products
Unlabeled Version(s)
90410Lipoxin A4
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Lipoxin A4-d5

Item No. 10007737

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5S,6R,15S-trihydroxyicosa-7E,9E,11Z,13E-tetraenoic-19,19,20,20,20-d5 acid
CAS Number
1622429-53-1
Synonyms
  • LXA4-d5
  • 5(S),6(R),15(S)-TriHETE-d5
Molecular Formula
C20H27D5O5
Formula Weight
357.5
Purity
≥99% deuterated forms (d1-d5)
Formulation
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
302 nm
SMILES
O[C@@H](CCCC([2H])([2H])C([2H])([2H])[2H])/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)CCCC(O)=O
InChi Code
InChI=1S/C20H32O5/c1-2-3-8-12-17(21)13-9-6-4-5-7-10-14-18(22)19(23)15-11-16-20(24)25/h4-7,9-10,13-14,17-19,21-23H,2-3,8,11-12,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,13-9+,14-10+/t17-,18+,19-/m0/s1/i1D3,2D2
InChi Key
IXAQOQZEOGMIQS-YUMLLTTFSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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.

Download most recent Certificate of Analysis for this product

    10 µg

    $219

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    25 µg

    $521

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    50 µg

    $986

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    Product Description

    Lipoxin A4-d5 (LXA4-d5) is intended for use as an internal standard for the quantification of LXA4 (Item No. 90410) by GC- or LC-MS. LXA4 is a trihydroxy fatty acid containing a conjugated tetraene, produced by the metabolism of 15-HETE or 15-HpETE with human leukocytes.1 LXA4 is equipotent to leukotriene B4 (LTB4) in inducing superoxide generation in human neutrophils at 0.1 µM.2 LXA4 is associated with several other biological functions including leukocyte activation, chemotaxis effects, natural killer cell inhibition, and monocyte migration and adhesion.2,3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Serhan, C.N., Nicolaou, K.C., Webber, S.E., et al. Lipoxin A. Stereochemistry and biosynthesis. The Journal of Biological Chemisty 261(35), 16340-16345 (1986).

    2. Serhan, C.N., Hamberg, M., and Samuelsson, B. Lipoxins: Novel series of biologically active compounds formed from arachidonic acid in human leukocytes. Proc. Natl. Acad. Sci. USA 81(17), 5335-5339 (1984).

    3. Ramstedt, U., Serhan, C.N., Nicolaou, K.C., et al. Lipoxin A-induced inhibition of human natural killer cell cytotoxicity: Studies on stereospecificity of inhibition and mode of action. J. Immunol. 138(1), 266-270 (1987).

    4. Maddox, J.F., and Serhan, C.N. Lipoxin A4 and B4 are potent stimuli for human monocyte migration and adhesion: Selective inactivation by dehydrogenation and reduction. J. Exp. Med. 183(1), 137-146 (1996).

    Product Citations

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

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

    Norris, P.C., Libreros, S., and Serhan, C.N. Resolution metabolomes activated by hypoxic environment. Sci. Adv. 5(10), eaax4895 (2019).

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

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

    Sorgi, C.A., Peti, A.P.F., Petta, T., et al. Comprehensive high-resolution multiple-reaction monitoring mass spectrometry for targeted eicosanoid assays. Sci. Data 5, 180167 (2018).

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

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

    Sasaki, A., Fukuda, H., Shiida, N., et al. Determination of ω-6 and ω-3 PUFA metabolites in human urine samples using UPLC/MS/MS. Anal. Bioanal. Chem. 407(6), 1625-1639 (2015).