An abundant, specific marker of oxidative injury
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Labeled Version(s)
10006654(±)5-iPF2α-VI-d11
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(±)5-iPF2α-VI

Item No. 16300

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(8β)-5,9α,11α-trihydroxy-prosta-6E,14Z-dien-1-oic acid
CAS Number
179094-11-2
Synonyms
  • iPF2α-I
  • Isoprostane F2α-I
  • 5-iso PGF2α-VI
  • 5-iso Prostaglandin F2α-VI
Molecular Formula
C20H34O5
Formula Weight
354.5
Purity
≥95%
Formulation (Request formulation change)
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): .5 mg/ml
SMILES
O[C@@H]1[C@@H](C/C=C\CC(O)=O)[C@@H](/C=C/[C@H](O)CCCCC)[C@H](O)C1
InChi Code
InChI=1S/C20H34O5/c1-2-3-4-5-6-7-10-16-17(19(23)14-18(16)22)13-12-15(21)9-8-11-20(24)25/h6-7,12-13,15-19,21-23H,2-5,8-11,14H2,1H3,(H,24,25)/b7-6-,13-12+/t15?,16-,17+,18-,19+/m1/s1
InChi Key
RZCPXIZGLPAGEV-SUHLLOIRSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    10 µg

    $65

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    25 µg

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    50 µg

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    100 µg

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    Product Description

    (±)5-iPF2α-VI is one of dozens of possible stereo- and regioisomeric isoprostanes which can be formed from arachidonic acid. To date, the most extensively studied of these is 8-isoprostane (8-epi-PGF2α, iPF2α-III).1,2 However, 8-isoprostane is a minor isoprostane constituent when compared to some of the other isomers which form in natural conditions of oxidative stress.3 (±)5-iPF2α-VI is an isoprostane from the unique Type VI class of isoprostanes. This class has been shown to be one of the major isoprostane products, in contrast to 8-isoprostane. In addition to being produced in greater abundance than 8-isoprostane, Type VI isoprostanes form internal lactones, which facilitates their extraction and purification from biological samples.3,4,5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Delanty, N., Reilly, M., Pratico, D., et al. 8-Epi PGF2α: Specific analysis of an isoeicosanoid as an index of oxidant stress in vivo. Br. J. Clin. Pharmacol. 42, 15-19 (1996).

    2. Reilly, M.P., Barry, P., Lawson, J.A., et al. Urinary 8-epi PGF2α: An index of oxidant stress in vivo. Fibrinolysis & Proteolysis 11, 81-84 (1997).

    3. Reilly, M.P., Pratico, D., Delanty, N., et al. Increased formation of distinct F2 isoprostanes in hypercholesterolemia. Circulation 98, 2822-2828 (1998).

    4. Li, H., Lawson, J.A., Reilly, M., et al. Quantitative high performance liquid chromatography/tandem mass spectrometric analysis of the four classes of F2-isoprostanes in human urine. Proc. Natl. Acad. Sci. USA 96(23), 13381-13386 (1999).

    5. 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).

    6. Praticò, D., Barry, O.P., Lawson, J.A., et al. IPF2α-I: An index of lipid peroxidation in humans. Proc. Natl. Acad. Sci. USA 95, 3449-3454 (1998).

    Product Citations

    Jovanović, V., Aziz, N.A., Lim, Y.T., et al. Lipid anti-lipid antibody responses correlate with disease activity in systemic lupus erythematosus. PLoS one 8(2), e55639 (2013).