8,12-iso-iPF2alpha-VI-1,5-lactone

F2 isoprostanes (F2-iPs) are thought to arise from the free radical-mediated peroxidation of phospholipid-bound arachidonic acid. They are cleaved, presumably by an unidentified phospholipase A2, and are found in the circulation and the urine. 8,12-iso-iPF2alpha-VI-1,5-lactone is a racemic mixture of the lactone forms of the free acid, 8,12-iso- iPF2alpha-VI. Previously called IPF2alpha -I, the free acid form, iPF2alpha-VI, is the most abundant F2-iP regioisomer measured in the urine of rats treated with CCl4 to induce lipid peroxidation. iPF2alpha-VI is the only regioisomer that undergoes lactonization, and this occurs slowly in vivo or can be driven chemically. The less polar lactone is readily separated from the free acid forms of iPF2alpha. While the level of iPF2alpha-VI in plasma, urine and organs is used as a biomarker for oxidative stress, some F2-iPs also evoke significant biological effects. It is not known if 8,12-iso-iPF2alpha-VI-1,5-lactone has important physiological effects.Formal Name: 6-((E)-2-((1R,2S,3R,5S)-3,5-dihydroxy-2-((Z)-oct-2-enyl)cyclopentyl)vinyl)tetrahydro-2H-pyran-2-one. Molecular Formula: C20H32O4. Formula Weight: 336.5. Purity: >98%. Formulation: (Request formulation change), A solution in methyl acetate. Solubility: DMF: 100 mg/ml, DMSO: 100 mg/ml, Ethanol: 100 mg/ml, PBS (pH 7.2): 1 mg/ml. SMILES: O[C@H]1[C@@H](C/C=C\CCCCC)[C@@H](/C=C/C2OC(CCC2)=O)[C@@H](O)C1. InChi Code: InChI=1S/C20H32O4/c1-2-3-4-5-6-7-10-16-17(19(22)14-18(16)21)13-12-15-9-8-11-20(23)24-15/h6-7,12-13,15-19,21-22H,2-5,8-11,14H2,1H3/b7-6-,13-12+/t15?,16-,17+,18+,19-/m0/s1. InChi Key: AWRLHDHWBSHXSP-DCOIXEBESA-N.