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6(S)-Lipoxin A4 Sale

(Synonyms: 5(S),6(S)-Lipoxin A4, 6-epi-Lipoxin A4, 6(S)-LXA4, 5(S),6(S),15(S)-TriHETE) 目录号 : GC41424

An isomer of LXA4

6(S)-Lipoxin A4 Chemical Structure

Cas No.:94292-80-5

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25μg
¥3,838.00
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50μg
¥7,298.00
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100μg
¥13,808.00
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Sample solution is provided at 25 µL, 10mM.

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产品描述

The lipoxins are trihydroxy fatty acids containing a 7,9,11,13-conjugated tetraene. Lipoxin A4 (LXA4) was first described as a metabolite of 15-HpETE and/or 15-HETE when added in vitro to isolated human leukocytes. 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. 6(S)-LXA4 is one of the original four metabolites first identified by Serhan, Nicolaou, and Samuelsson. 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.

Chemical Properties

Cas No. 94292-80-5 SDF
别名 5(S),6(S)-Lipoxin A4, 6-epi-Lipoxin A4, 6(S)-LXA4, 5(S),6(S),15(S)-TriHETE
Canonical SMILES CCCCCCC(O)\C=C\C=C/C=C\C=C/C(O)C(O)CCCC(=O)O
分子式 C20H32O5 分子量 352.5
溶解度 DMF: 50 mg/ml,Ethanol: 50 mg/ml,PBS (pH 7.2): 1 mg/ml 储存条件 Store at -20°C
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1 mM 2.8369 mL 14.1844 mL 28.3688 mL
5 mM 0.5674 mL 2.8369 mL 5.6738 mL
10 mM 0.2837 mL 1.4184 mL 2.8369 mL
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Research Update

Conversion of 5,6-dihydroxyeicosatetraenoic acids. A novel pathway for lipoxin formation by human platelets

FEBS Lett 1992 Jun 8;304(1):78-82.PMID:1618303DOI:10.1016/0014-5793(92)80593-6

Leukotriene A4 may be metabolized to 5(S),6(R)- and 5(S),6(S)-dihydroxy-7,9-trans-11,14-cis-eicosatetraenoic acids by enzymatic or non-enzymatic hydrolysis. Incubation of human platelet suspensions with these dihydroxy acids led to the formation of lipoxin A4 and 6(S)-Lipoxin A4 via lipoxygenation at C-15. Furthermore, human platelets converted the two 5(R),6(S)- and 5(R),6(R)-dihydroxy-7,9-trans-11,14-cis-eicosatetraenoic acids to tetraene-containing trihydroxyeicosatetraenoic acids. In contrast, leukotrienes C4, D4 and E4 were not transformed to cysteinyl-lipoxins. Time-course studies of leukotriene A4 metabolism in human platelet suspensions indicated lipoxin formation via two pathways: (i) direct conversion of leukotriene A4, leading to formation of the lipoxin intermediate 15-hydroxy-leukotriene A4; and (ii) 15-lipoxygenation of the 5(S),6(R)- and 5(S),6(S)-dihydroxyeicosatetraenoic acids. The results demonstrate that lipoxygenation at C-15 of 5,6-dihydroxy-7,9,11,14-eicosatetraenoic acids may be an alternative novel pathway for platelet-dependent lipoxin formation.