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5(S),6(R)-Lipoxin A4 methyl ester

Cayman Chemical Item Number 10033

5(S),6(R)-LXA4 methyl ester; 5(S),6(R),15(S)-TriHETE methyl ester (CAS 97643-35-1)

5(S),6(R)-Lipoxin A4 methyl ester (CAS 97643-35-1)

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Description

5(S),6(R)-Lipoxin A4 methyl ester (5(S),6(R)-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 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).

Synonyms
  • 5(S),6(R)-LXA4 methyl ester
  • 5(S),6(R),15(S)-TriHETE methyl ester
Formal Name 5S,​6R,​15S-​trihydroxy-​7E,​9E,​11Z,​13E-​eicosatetraenoic acid,​ methyl ester
CAS Number 97643-35-1
Molecular Formula C21H34O5
Formula Weight 366.5
Formulation A solution in ethanol
Purity >95%
λmax 302 nm
ε 50
Stability 1 year
Storage -80°C
Shipping Dry ice in continental US; may vary elsewhere
SMILES
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CCCCC[C@@H]​(O)​/C=C/C=C\C=C\C=C\[C@@H]​(O)​[C@@H]​(O)​CCCC(OC)​=O

Background Reading

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).

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).

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).

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5(S),6(R)-Lipoxin A4 methyl ester is available in the following screening library:

Size Price Quantity Subtotal
25 µg $213.00 $0.00
50 µg $405.00 $0.00
100 µg $767.00 $0.00
250 µg $1,704.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-05-25. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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