An internal standard for the quantification of (±)5-iPF2α-VI
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Unlabeled Version(s)
16300(±)5-iPF2α-VI
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(±)5-iPF2α-VI-d11

Item No. 10006654

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(±)5,9α,11α-trihydroxy-(8β)-prosta-6E,14Z-dien-1-oic-16,16,17,17,18,18,19,19,20,20,20-d11 acid
CAS Number
936565-17-2
Molecular Formula
C20H23D11O5
Formula Weight
365.6
Purity
≥99% deuterated forms (d1-d11)
Formulation
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): 1 mg/ml
SMILES
CCCCC/C=C\C[C@H]1C(O)CC(O)[C@H]1\C=C\C(O)CCCC(=O)O
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/i1D3,2D2,3D2,4D2,5D2
InChi Key
RZCPXIZGLPAGEV-AOORLBIGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    10 µg

    $438

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    25 µg

    $1,041

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    Product Description

    (±)5-iPF2α-VI-d11 contains 11 deuterium atoms at the 16, 16, 17, 17, 18, 18, 19, 19, 20, 20, and 20 positions. It is intended for use as an internal standard for the quantification of (±)5-iPF2α-VI (Item No. 16300) by GC- or LC-mass spectrometry. Isoprostanes are prostaglandin-like products of free-radical induced lipid peroxidation.1 Although the isoprostanes derived from arachidonic acid are the best characterized, many other polyunsaturated fatty acids can form isoprostanes.2 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).3,4 However, 8-isoprostane is a minor isoprostane constituent when compared to some of the other isomers which form in natural conditions of oxidative stress,5 including iPF2α-VI of the type-VI 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 facilitate their extraction and purification from biological samples.5,6,7,8

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. Parchmann, S., and Mueller, M.J. Evidence for the formation of dinor isoprostanes E1 from α-linolenic acid in plants. The Journal of Biological Chemisty 273, 32650-32655 (1998).

    3. 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).

    4. 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).

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

    6. 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).

    7. 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).

    8. 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).