8-iso-15-keto Prostaglandin F

Cayman Chemical Item Number 16390

8-epi-15-keto PGF; 8-iso-15-keto PGF (CAS 191919-01-4)

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Description

8-iso-15-keto Prostaglandin F (8-iso-15-keto PGF) is a metabolite of the isoprostane 8-iso PGF in rabbits, monkeys, and humans. 8-isoprostane (8-iso PGF) is a prostaglandin-like product of non-specific lipid peroxidation.1 In both humans and monkeys, exogenously infused 8-iso PGF is converted primarily to metabolites having 2 or 4 carbon atoms removed from the top side chain by β-oxidation.2 A similar pattern is observed when tritiated 8-iso PGF is infused into rabbits.3 Early in the infusion (within 1-2 minutes) 8-iso -15-keto PGF was a major component of the metabolite profile, which was comprised mostly of unmetabolized 8-iso PGF. 8-iso -15-keto PGF is a vasoconstrictor when tested on the rat isolated thoracic aorta, acting via the TP (thromboxane) receptor.4

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. Chiabrando, C., Valagussa, A., Rivalta, C., et al. Identification and measurement of endogenous β-oxidation metabolites of 8-epi-prostaglandin F2a. J Biol Chem 274 1313-1319 (1999).

3. Basu, S. Metabolism of 8-iso-prostaglandin F. FEBS Lett 428 32-36 (1998).

4. Cracowski, J., Camus, L., Durand, T., et al. Response of rat thoracic aorta to F2-isoprostane metabolites. J Cardiovasc Pharmacol 39 396-403 (2002).

Synonyms
  • 8-epi-15-keto PGF
  • 8-iso-15-keto PGF
Formal Name 9α,​11α-​dihydroxy-​15-​oxo-​(8β)-​prosta-​5Z,​13E-​dien-​1-​oic acid
CAS Number 191919-01-4
Molecular Formula C20H32O5
Formula Weight 352.5
Formulation A solution in methyl acetate
Purity ≥95%
λmax 230 nm
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O[C@@H]​1[C@@H]​(C/C=C\CCCC(O)​=O)​[C@@H]​(/C=C/C(CCCCC)​=O)​[C@H]​(O)​C1
InCHI Code
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​1S/C20H32O5/c1-2-3-6-9-15(21)​12-13-17-16(18(22)​14-19(17)​23)​10-7-4-5-8-11-20(24)​25/h4,7,12-13,16-19,22-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)​/b7-4-,13-12+/t16-,17+,18-,19+/m0/s1
InCHI Key
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LOLJEILMPWPILA-RLXHZABYSA-N

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8-iso-15-keto Prostaglandin F is available in the following screening library:

Size Price Quantity Subtotal
100 µg $25.00 $0.00
500 µg $75.00 $0.00
1 mg $138.00 $0.00
Bulk Contact
Cart Total $0.00

Pricing updated 2015-07-05. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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8-iso-15-keto Prostaglandin F

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