See personalized New Product recommendations! Get personalized New Product recommendations! Register or Login for personalized New Product recommendations!

Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

5-iPF2α-VI Exclusive

Cayman Chemical Item Number 16300

iPF2α-I (CAS 180469-63-0)

5-iPF2α-VI (CAS 180469-63-0)

See more

Description

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 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 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.5,6,7,8

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 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. J Biol Chem 273 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).

Synonyms
  • iPF2α-I
Formal Name (±)5,​9α,​11α-​trihydroxy-​(8β)-​prosta-​6E,​14Z-​dien-​1-​oic acid
CAS Number 180469-63-0
Molecular Formula C20H34O5
Formula Weight 354.5
Formulation A solution in ethanol
Purity ≥95%
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
CCCCC/C=C\C[C@H]​1C(O)​CC(O)​[C@H]​1\C=C\C(O)​CCCC(=O)​O

Background Reading

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).

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).

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. J Biol Chem 273 29295-29301 (1998).

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).

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).

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

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).

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).

Show all 8 Hide all but first 3

5-iPF2α-VI is available in the following screening library:

Size Price Quantity Subtotal
10 µg $44.00 $0.00
50 µg $198.00 $0.00
100 µg $352.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-02-12. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

Related Products

5-iPF2α-VI-d11
8,12-iso-iPF2α-VI-d11 Exclusive
iPF2α-VI-d4
iPF2α-VI EIA Kit
Show all 4 Hide all but first 3

Downloads

Batch-specific Information

Login to access batch-specific information

Cayman Chemical is a manufacturer, supplier and vendor of biochemical reagents, assay kits, antibodies, and proteins.

Other Resources
Management Team Company Profile Company History ChemAssistant Tools FAQs Cayman Europe Cayman Pharma CaBRI Cayman Gear Press Releases Illustrations and Charts Key Research Area Posters Article Library Analysis Tools Conference Schedule Order Terms Browser Recommendation Privacy Statement Site Map

Cayman Chemical Company · 1180 East Ellsworth Road · Ann Arbor, Michigan 48108 · USA

Toll Free: (800) 364-9897 (USA and Canada Only) · Fax: (734) 971-3640

Copyright 2012 Cayman Chemical Company

Lost password?