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iPF2α-VI-d4

Cayman Chemical Item Number 316300

8-iso-5(R),6E,14Z-Prostaglandin F2α-d4 (CAS 214977-79-4)

iPF2α-VI-d4 (CAS 214977-79-4)

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Description

iPF2α-VI-d4 contains four deuterium atoms at the 17, 17', 18, and 18' positions. It is intended for use as an internal standard for the quantification of iPF2α-VI 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 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

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
  • 8-iso-5(R),6E,14Z-Prostaglandin F2α-d4
Formal Name 5S,​9α,​11α-​trihydroxy-​(8β)-​prosta-​6E,​14Z-​dien-​1-​oic-​17,​17,​18,​18-​d4 acid
CAS Number 214977-79-4
Molecular Formula C20H30D4O5
Formula Weight 358.5
Formulation A solution in methyl acetate
Purity ≥99% deuterated forms (d1-d4)
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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CCCCC/C=C\C[C@H]​1[C@H]​(O)​C[C@H]​(O)​[C@H]​1\C=C\[C@@H]​(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).

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).

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).

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).

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).

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).

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).

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Size Price Quantity Subtotal
10 µg $123.00 $0.00
25 µg $292.00 $0.00
50 µg $554.00 $0.00
100 µg $984.00 $0.00
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Cart Total $0.00

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

Pricing updated 2012-05-26. 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.

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FAQs

It appears that there is a heterogenous mixture of deuterated species in your deuterated standards; is this normal?

Yes, this is typical of our deuterated products. Our deuterated products contain less than 1 % d0. However, the labeled compounds are not 100% of the deuterated form listed on our product insert. For example, upon analysis of 2-arachidonoyl glycerol-d8 it is expected to see masses associated with the d7, d6, d5 etc.

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