A deuterated internal standard for a predominant isoprostane isomer
Related Products
Unlabeled Version(s)
163108,12-iso-iPF2α-VI
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8,12-iso-iPF-VI-d11

Item No. 10006878

Technical Information
Formal Name
(12α)-5,9α,11α-trihydroxy-prosta-6E,14Z-dien-1-oic-16,16,17,17,18,18,19,19,20,20,20-d11 acid
CAS Number
1616977-85-5
Synonyms
  • 8,12-iso-Isoprostane-F-VI-d11
  • 12-iso-5,6E,14Z-PGF-d11
  • 12-iso-5,6E,14Z-Prostaglandin F-d11
Molecular Formula
C20H23D11O5
Formula Weight
Purity
≥99% deuterated forms (d1-d11)
Formulation
A 50 µg/ml solution in acetonitrile
DMF: >100mg/ml (PGF2 alpha)DMSO: >100mg/ml (PGF2 alpha)Ethanol: >100mg/ml (PGF2 alpha)PBS pH 7.2: 3 mg/ml (PGF2 alpha)
SMILES
OC(CCCC(O)=O)/C=C/[C@@H]1[C@H](C/C=C\C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])[2H])[C@H](O)C[C@@H]1O
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-/m0/s1/i1D3,2D2,3D2,4D2,5D2
InChi Key
RZCPXIZGLPAGEV-JVUJZTPFSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    Product Description

    8,12-iso-isoprostane F-VI-d11 (8,12-iso-iPF-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 8,12-iso-iPF-VI by GC- or LC-mass spectrometry. The relative abundance of deuterium atoms incorporated into each molecule has not been determined. Cayman certifies that less that 1% of the product has no deuterium incorporation (<1% d0). Isoprostanes are non-enzymatic, non-cyclooxygenase prostanoid products of peroxidative damage to membrane lipids.1 Among the many isoprostane isomers, 8,12-iso-iPF-VI has been demonstrated to be one of the predominant isomers formed and is also present in urine as one of the major isoprostane products.2 8,12-iso-iPF-VI-d11 is a deuterated internal standard for use in isoprostane quantitation by mass spec modalities. The compound is diastereomeric at C-5, but is otherwise an optically active, single enantiomer.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Diaz, M.N., Frei, B., Vita, J.A., et alAntoixidants and atherosclerotic heart disease. New Engl. J. Med. 337(6), 408-416 (1997).

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