An isomer of LXA4
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6(S)-Lipoxin A4

Item No. 10049

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5S,6S,15S-trihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid
CAS Number
94292-80-5
Synonyms
  • 5(S),6(S)-Lipoxin A4
  • 6-epi-Lipoxin A4
  • 6(S)-LXA4
  • 5(S),6(S),15(S)-TriHETE
Molecular Formula
C20H32O5
Formula Weight
352.5
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(O)=O
InChi Code
InChI=1S/C20H32O5/c1-2-3-8-12-17(21)13-9-6-4-5-7-10-14-18(22)19(23)15-11-16-20(24)25/h4-7,9-10,13-14,17-19,21-23H,2-3,8,11-12,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,13-9+,14-10+/t17-,18-,19-/m0/s1
InChi Key
IXAQOQZEOGMIQS-UZDWIPAXSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    25 µg

    $347

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    50 µg

    $659

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    Product Description

    6(S)-Lipoxin A4 (6(S)-LXA4) is an isomer of the trihydroxy fatty acid LXA4 (Item No. 90410). It is formed from arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) through double lipoxygenase-catalyzed reactions initiated by either 5-lipoxygenase (5-LO) followed by 12- or 15-LO, with a leukotriene A4 (LTA4) intermediate, or by 15-LO followed by 5-LO, with 15(S)-HETE (Item No. 34720) and 5(S)-Hp-15(S)-HETE intermediates.1 The generation of 6(S)-LXA4 and LXA4 typically requires transcellular metabolism of arachidonic acid.1,2 For example, LTA4 synthesized in neutrophils by 5-LO is metabolized to LXA4 in platelets by 12-LO.1 6(S)-LXA4 has been detected in co-incubations of human polymorphonuclear leukocytes (PMNs) and platelets.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Serhan, C.N., and Sheppard, K.-A. Lipoxin formation during human neutrophil-platelet interactions. Evidence for the transformation of leukotriene A4 by platelet 12-lipoxygenase in vitro. J. Clin. Invest. 85(3), 772-780 (1990).

    2. Serhan, C.N., Chiang, N., and Van Dyke, T.E. Resolving inflammation: Dual anti-inflammatory and pro-resolution lipid mediators. Nat. Rev. Immunol. 8(5), 349-361 (2008).

    3. Homann, J., Lehmann, C., Kahnt, A.S., et al. Chiral chromatography-tandem mass spectrometry applied to the determination of pro-resolving lipid mediators. J. Chromatogr. A 1360, 150-163 (2014).

    Product Citations

    Hartling, I., Cremonesi, A., Osuna, E., et al. Quantitative profiling of inflammatory and pro-resolving lipid mediators in human adolescents and mouse plasma using UHPLC-MS/MS. Clin. Chem. Lab. Med. 59(11), 1811-1823 (2021).

    Kutzner, L., Rund, K.M., Ostermann, A.I., et al. Development of an optimized LC-MS method for the detection of specialized pro-resolving mediators in biological samples. Front. Pharmacol. 10, 169 (2019).