5-iPF2α-VI • iPF<sub>2α</sub>-<wbr/>I (CAS 180469-63-0) (Inchi key RZCPXIZGLPAGEV-SUHLLOIRSA-N) || Cayman Chemical | Supplier
5-iPF-VI
Item № 16300
CAS № 180469-63-0
Purity ≥95%
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SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL $0.00
10 µg $46.00 $0.00
25 µg $109.00 $0.00
50 µg $207.00 $0.00
100 µg $368.00 $0.00

Pricing updated 2015-08-29. Prices are subject to change without notice.

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Description
Synonyms
  • iPF-I

Isoprostanes are prostaglandin (PG)-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 iPF-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-PGF, iPF-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 iPF-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.5,6,7,8

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Technical Information
Formal Name 5,​9α,​11α-​trihydroxy-​(8β)-​prosta-​6E,​14Z-​dien-​1-​oic acid
CAS Number 180469-63-0
Synonyms
  • iPF-I
Molecular Formula C20H34O5
Formula Weight 354.5
Purity ≥95%
Formulation A solution in ethanol
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 ​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

WARNING - This product is not for human or veterinary use.

Shipping & Storage
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
Stability 1 year
Product Downloads & Resources
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Download Product Insert 107 Kb PDF

Download Safety Data Sheet (SDS) 31 Kb PDF

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Additional Information

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References & Background Reading
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 9383-9387 (1990).

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

3. Delanty, N., Reilly, M., Pratico, D., et al. 8-Epi PGF: 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 PGF: 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 F-VI, in human urine. J Biol Chem 273 29295-29301 (1998).

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

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