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Cat. Number
652586964038794
Chemical Name
5(S),6(R)-Lipoxin A4 Lipid Maps MS Standard
References
Synonyms
  • 5(S),6(R),15(S)-TriHETE
  • 5(S),6(R)-LXA4
Formal Name 5S,​6R,​15S-​trihydroxy-​7E,​9E,​11Z,​13E-​eicosatetraenoic acid
CAS Number 89663-86-5
Molecular Formula C20H32O5
Formula Weight 352.5
Formulation A solution in ethanol
Purity ≥95%
Stability 1 year
Storage -80°C
Shipping Dry ice in continental US; may vary elsewhere
SMILES CCCCCC(O)​C=C/C=C/C=CC=C/[C@@H]​(O)​C(O)​CCCC(=O)​O

Background Reading

Serhan, C.N., Hamberg, M., Samuelsson, B., et al. On the stereochemistry and biosynthesis of lipoxin B. Proc Natl Acad Sci USA 83 1983-1987 (1986).

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 138 266-270 (1987).

Serhan, C.N., Nicolaou, K.C., Webber, S.E., et al. Lipoxin A. Stereochemistry and biosynthesis. J Biol Chem 261 16340-16345 (1986).

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 5335-5339 (1984).

Kim, S.J., and Tominaga, T. Formation of lipoxins by the brain. Ann N Y Acad Sci 559 461-464 (1989).

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 183 137-146 (1996).

Serhan, C.N. Lipoxin biosynthesis and its impact in inflammatory and vascular events. Biochim Biophys Acta 1212 1-25 (1994).

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Description

5(S),6(R)-Lipoxin A4 (LXA4) is a trihydroxy fatty acid containing a conjugated tetraene, produced by the metabolism of 15-HETE or 15-HpETE with human leukocytes.1 5(S),6(R)-LXA4 is equipotent to leukotriene B4 (LTB4) in inducing superoxide generation in human neutrophils at 0.1 µM.2 5(S),6(R)-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

1 Serhan, C.N., Nicolaou, K.C., Webber, S.E., et al. Lipoxin A. Stereochemistry and biosynthesis. J Biol Chem 261 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 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 138 266-270 (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 183 137-146 (1996).

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