5-iPF-VI

Cayman Chemical Item Number 16300

iPF-I (CAS 180469-63-0)

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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 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

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).

Synonyms
  • iPF-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
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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
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​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
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RZCPXIZGLPAGEV-SUHLLOIRSA-N

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

Size Price Quantity Subtotal
10 µg $46.00 $0.00
25 µg $109.00 $0.00
50 µg $207.00 $0.00
100 µg $368.00 $0.00
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Cart Total $0.00

Pricing updated 2015-07-30. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

Related Products

5-iPF-VI-d11
8,12-iso-iPF-VI-d11
iPF-VI-d4

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Cayman Chemical Company regularly evaluates our shipping methods to ensure product stability is maintained and our corporate environmental impact is minimized. Products selected for review are evaluated and shipping methods are certified by our Scientists. While occasionally our method of shipping a product may change, rest assured the shipping conditions on all Cayman Chemical products have been reviewed and validated.

Upon receipt, it is important to check the storage requirements of your products and place them at the appropriate temperature. Products shipped without ice may require frozen storage for long term stability.

Cayman Chemical was formed over thirty years ago by demonstrating the value of naturally growing gorgonian corals as a renewable, economically viable source of prostaglandins. Today we operate our business knowing that we owe our start to the renewable resources our environment had provided. As Cayman Chemical continues to grow we consistently evaluate our business processes to ensure we are operating at the highest environmental standards.

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Ann Arbor, Michigan 48108 USA

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