A lipid soluble, prodrug of LXA4
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Lipoxin A4 methyl ester

Item No. 10033

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5S,6R,15S-trihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid, methyl ester
CAS Number
97643-35-1
Synonyms
  • LXA4 methyl ester
  • 5(S),6(R),15(S)-TriHETE methyl ester
Molecular Formula
C21H34O5
Formula Weight
366.5
Purity
≥95%
Formulation (Request formulation change)
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
CCCCC[C@@H](O)/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)CCCC(OC)=O
InChi Code
InChI=1S/C21H34O5/c1-3-4-9-13-18(22)14-10-7-5-6-8-11-15-19(23)20(24)16-12-17-21(25)26-2/h5-8,10-11,14-15,18-20,22-24H,3-4,9,12-13,16-17H2,1-2H3/b7-5-,8-6+,14-10+,15-11+/t18-,19+,20-/m0/s1
InChi Key
UBPCKDCSZPRQJP-QDCMSWGPSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    25 µg

    $302

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    50 µg

    $571

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    100 µg

    $1,078

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    Product Description

    Lipoxin A4 (LXA4) methyl ester is a more lipid soluble, prodrug formulation of the transcellular metabolite LXA4. 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).