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Eoxin A4

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Eoxin A4
Names

Preferred IUPAC name (5Z,8Z,10E,12E)-13-[(2S,3S)-3-Pentyloxiran-2-yl]trideca-5,8,10,12-tetraenoic acid
Other names EXa4; 14,15-LTA4
Identifiers
CAS Number	81918-96-9^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:63983
ChemSpider	27471348
PubChem CID	52921883
CompTox Dashboard (EPA)	DTXSID801032105
InChI InChI=1S/C20H30O3/c1-2-3-12-15-18-19(23-18)16-13-10-8-6-4-5-7-9-11-14-17-20(21)22/h4,6-10,13,16,18-19H,2-3,5,11-12,14-15,17H2,1H3,(H,21,22)/b6-4-,9-7-,10-8+,16-13+/t18-,19-/m0/s1 Key: URDQSJSEGRMOIT-FDMWOPBLSA-N
SMILES CCCCC[C@H]1[C@@H](O1)/C=C/C=C/C=C\C/C=C\CCCC(=O)O
Properties
Chemical formula	C₂₀H₃₀O₃
Molar mass	318.457 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Eoxin A4, also known as 14,15-leukotriene A4, is an eoxin. Cells make eoxins by metabolizing arachidonic acid with a 15-lipoxygenase enzyme to form 15(S)-hydroperoxyeicosapentaenoic acid (i.e. 15(S)-HpETE). This product is then converted serially to eoxin A4 (i.e. EXA4), EXC4, EXD4, and EXE4byLTC4 synthase, an unidentified gamma-glutamyltransferase, and an unidentified dipeptidase, respectively, in a pathway which appears similar if not identical to the pathway which forms leukotreines, i.e. LTA4, LTC4, LTD4, and LTE4. This pathway is schematically shown as follows:^[1]^[2]

Arachidonic acid + O₂ → 15(S)-HpETE → EXA4 → EXC4 → EXD4 → EXE4

EXA₄ is viewed as an intracellular-bound, short-lived intermediate which is rapidly metabolized to the down-stream eoxins. The eoxins down stream of EXA4 are secreted from their parent cells and, it is proposed but not yet proven, serve to regulate allergic responses and the development of certain cancers (see Eoxins).^[1]^[3]

References

[edit]

^ ^a ^b Claesson HE (September 2009). "On the biosynthesis and biological role of eoxins and 15-lipoxygenase-1 in airway inflammation and Hodgkin lymphoma". Prostaglandins Other Lipid Mediat. 89 (3–4): 120–5. doi:10.1016/j.prostaglandins.2008.12.003. PMID 19130894.