Lactone form of 8,12-iso-iPF2α-VI
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8,12-iso-iPF2α-VI-1,5-lactone

Item No. 10312

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
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 100 µg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 100 mg/mlDMSO: 100 mg/mlEthanol: 100 mg/mlPBS (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
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    25 µg

    $128

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    50 µg

    $241

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    100 µg

    $454

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    Product Description

    F2 isoprostanes (F2-iPs) are thought to arise from the free radical-mediated peroxidation of phospholipid-bound arachidonic acid.1 They are cleaved, presumably by an unidentified phospholipase A2, and are found in the circulation and the urine. 8,12-iso-iPF2α-VI-1,5-lactone is a racemic mixture of the lactone forms of the free acid, 8,12-iso- iPF2α-VI. Previously called IPF2α -I,2 the free acid form, iPF2α-VI, is the most abundant F2-iP regioisomer measured in the urine of rats treated with CCl4 to induce lipid peroxidation.3 iPF2α-VI is the only regioisomer that undergoes lactonization, and this occurs slowly in vivo or can be driven chemically.4 The less polar lactone is readily separated from the free acid forms of iPF2α.4 While the level of iPF2α-VI in plasma, urine and organs is used as a biomarker for oxidative stress,5,6 some F2-iPs also evoke significant biological effects.7 It is not known if 8,12-iso-iPF2α-VI-1,5-lactone has important physiological effects.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lawson, J.A., Li, H., Rokach, J., et al. Identification of two major F2 isoprostanes, 8,12-iso- and 5-epi-8,12-iso-isoprostane F2α-VI, in human urine. The Journal of Biological Chemisty 273(45), 29295-29301 (1998).

    2. Morrow, J.D., Hill, K.E., Burk, R.F., et al. A series of prostaglandin F2-like compounds are produced in vivo in humans by a non-cyclooxygenase, free radical-catalyzed mechanism. Proc. Natl. Acad. Sci. USA 87(23), 9383-9387 (1990).

    3. Waugh, R.J., Morrow, J.D., Roberts, L.J., II, et al. Identification and relative quantitation of F2-isoprostane regioisomers formed in vivo in the rat. Free Radic. Biol. Med. 23(6), 943-954 (1997).

    4. Adiyaman, M., Lawson, J.A., Khanapure, S.P., et al. Total synthesis of 17,17,18,18-d4-iPF2α-VI and quantification of iPF2α-VI in human urine by gas chromatography/mass spectrometry. Anal. Biochem. 262(1), 45-56 (1998).

    5. Practico, D., Barry, O.P., Lawson, J.A., et al. IPF2a-I: An index of lipid peroxidation in humans. Proc. Natl. Acad. Sci. USA 95(7), 3449-3454 (1998).

    6. Van Eck, M., Hoekstra, M., Hildebrand, R.B., et al. Increased oxidative stress in scavenger receptor BI knockout mice with dysfunctional HDL. Arterioscler. Thromb. Vasc. Biol. 27(11), 2413-2419 (2007).

    7. Gardi, C., Arezzini, B., Monaco, B., et al. F2-isoprostane receptors on hepatic stellate cells. Lab. Invest. 88, 124-131 (2008).