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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

5(S),6(S)-Lipoxin A4

Cayman Chemical Item Number 10049

5(S),6(S),15(S)-TriHETE; 5(S),6(S)-LXA4

5(S),6(S)-Lipoxin A4

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Description

The lipoxins are trihydroxy fatty acids containing a 7,9,11,13-conjugated tetraene.1 Lipoxin A4 (LXA4) was first described as a metabolite of 15-HpETE and/or 15-HETE when added in vitro to isolated human leukocytes.2 The material obtained in this manner consists of at least four distinct isomers: 5(S), 6(S); 5(S), 6(R); and the 11-trans and 11-cis isomers of each of these. 5(S),6(S)-LXA4 is one of the original four metabolites first identified by Serhan, Nicolaou, and Samuelsson.2 It was considered to be an artifact by these authors because it lacked the potency of the 5(S),6(R) isomer with respect to contraction of isolated guinea pig lung parenchymal strips. It has not been possible to isolate “natural” LXA4 from humans or other mammals in amounts sufficient for determination of absolute stereochemistry. Most authors refer to LXA4 as the 5(S),6(R), 11-cis isomer, but it is not clear that biological systems are aware of or agree with these conventions. Historically, conjugated tetraenes flanked by hydroxyl groups of mixed stereochemistry have been marketed as 'Lipoxin A4' by some biomolecular supply companies. The availability of single pure LXA4 enantiomers should help to reduce the confusion this has caused.

1 Samuelsson, B., Dahlén, S., Lindgren JÅ, et al. Leukotrienes and lipoxins: Structures, biosynthesis, and biological effects. Science 237 1171-1176 (1987).

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

Synonyms
  • 5(S),6(S),15(S)-TriHETE
  • 5(S),6(S)-LXA4
Formal Name 5S,​6S,​15S-​trihydroxy-​7E,​9E,​11Z,​13E-​eicosatetraenoic acid
Molecular Formula C20H32O5
Formula Weight 352.5
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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CCCCCCC(O)​\C=C\C=C/C=C\C=C/C(O)​C(O)​CCCC(=O)​O

Background Reading

Samuelsson, B., Dahlén, S., Lindgren JÅ, et al. Leukotrienes and lipoxins: Structures, biosynthesis, and biological effects. Science 237 1171-1176 (1987).

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

5(S),6(S)-Lipoxin A4 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.

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Pricing updated 2012-02-11. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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