8-iso Prostaglandin E2 | CAS 27415-25-4

Element: prostaglandin

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C-S » Chemicals » iso-prostaglandin-PX73561

Identification

8-iso Prostaglandin E2

CAS:

27415-25-4

EINECS:

Molecular Formula:

C₂₀H₃₂O₅

MDL:

SMILES:

CCCCCC(O)/C=C/[C@H]1C(O)CC(=O)[C@H]1C/C=CCCCC(=O)O

Synonym:

8-iso prostaglandin e2 exclusive ; 8-iso prostaglandin e2 ; 9-oxo-11alpha,15s-dihydroxy-(8beta)-prosta-5z,13e-dien-1-oic acid ; (z)-7-[(1s,2r,3r)-3-hydroxy-2-[(e,3s)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid

Description

8-iso Prostaglandin E₂ is the epimer at C8 of PGE2 and is one of several isoprostanes produced from arachidonic acid during lipid peroxidation. This compound has been shown to be a potent renal vasoconstrictor in the rat, and to inhibit U-46619 or I-BOP-induced platelet aggregation with IC₅₀ values of 0.5 and 5 μM, respectively. Interestingly it has been reported that this compound also relaxes smooth muscle and has been shown to cause vasodilation of porcine coronary artery. Furthermore, 8-iso Prostaglandin E₂ demonstrated brochodilation in porcine tracheal smooth muscle via K⁺ current suppression caused by activation of thromboxane A2 receptors.