Hepoxilin

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Hepoxilin A3
IUPAC name (5E,9E)-8-hydroxy-10-[3-[(E)-oct-2-enyl] -2-oxiranyl]deca-5,9-dienoic acid
Other names HXA3
Identifiers
CAS number
PubChem 5353666
SMILES CCCCCC=CCC1C(O1)C=CC(CC=CCCCC(=O)O)O
Properties
Molecular formula C20H32O4
Molar mass 336.46568
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

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Hepoxilins (HxA3 and HxB3) are nonclassic eicosanoid hormones involved in inflammation.

History

Hepoxilins were identified and named in Canada in 1984 by CR Pace-Asciak and JM Martin.[1]

Biochemistry

They derive from arachidonic acid via oxidation by the enzyme 12-lipoxygenase. Hepoxilins are differentiated from closely related eicosanoids, the leukotrienes and the lipoxins, in that hepoxilins have no conjugated double bonds. Corresponding trioxlins A4 and B4 are formed by the same pathway from EPA [1]

Physiological effect

In the skin, Hx are pro-inflammatory, but in neutrophils they are anti-inflammatory.[1] Hx are potent insulin secretagogues.[1] One hepoxilin, HepA3, mediates neutrophil migration across the intestines.[1] Hepoxilins are also produced in the brain.[1] Cells under oxidative stress secrete HX3, which in turn upregulates peroxidase, decreasing oxidative stress. This is proposed to constitute a compensatory defense response to protect the vitality and functionality of the cell.[1]

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Acknowledgement and Attribution Regarding Sources of Content

Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .

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