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ChemicalBook--->CAS DataBase List--->191919-02-5

191919-02-5

191919-02-5 Structure

191919-02-5 Structure
IdentificationBack Directory
[Name]

(Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid
[CAS]

191919-02-5
[Synonyms]

VKTIONYPMSCHQI-JPRPWBOBSA-N
8-iso-13,14-dihydro-15-keto-PGF2a
8-iso-13,14-dihydro-15-keto Prostaglandin F2α
(Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid
[Molecular Formula]

C20H34O5
[MOL File]

191919-02-5.mol
[Molecular Weight]

354.48
Chemical PropertiesBack Directory
[Boiling point ]

543.0±40.0 °C(Predicted)
[density ]

1.091±0.06 g/cm3(Predicted)
[storage temp. ]

Store at -20°C
[solubility ]

10 mM Na2CO3: >6.5 mg/ml; DMF: >100 mg/ml; DMSO: >100 mg/ml; Ethanol: >100 mg/ml; PBS (pH 7.2): >10 mg/ml
[pka]

4.76±0.10(Predicted)
Safety DataBack Directory
[Symbol(GHS) ]


GHS02,GHS07,GHS08
[Signal word ]

Danger
Hazard InformationBack Directory
[Description]

8-iso-13,14-dihydro-15-keto Prostaglandin F (8-iso-13,14-dihydro-15-keto PGF) is a metabolite of the isoprostane, 8-isoprostane (8-iso PGF), in rabbits, monkeys and humans.1 8-iso PGF is a PG-like product of non-specific lipid peroxidation.2 In both humans and monkeys, exogenously infused 8-isoprostane is converted primarily to metabolites having 2 or 4 carbon atoms removed from the top side chain by β-oxidation.1 A similar pattern is observed when tritiated 8-isoprostane is infused into rabbits.3 Early in the infusion (within 10 minutes) 8-iso-13,14-dihydro-15-keto PGF was a significant component of the metabolite profile, which was comprised mostly of dinor 8-isoprostane metabolites. 8-iso-13,14-dihydro-15-keto PGF weakly inhibits the U-46619 or collagen-induced aggregation of human platelets, although a number of the E-series isoprostanes are much more potent in this assay.4
[Uses]

8-iso-13,14-dihydro-15-keto Prostaglandin F2α is an oxidative metabolite of 8-iso-prostaglandin F2α (HY-113209). 8-iso-13,14-dihydro-15-keto Prostaglandin F2α can be used in the study of oxidative stress-related diseases[1].
[References]

1. Chiabrando, C., Valagussa, A., Rivalta, C., et al. Identification and measurement of endogenous β-oxidation metabolites of 8-epi-prostaglandin F J. Biol. Chem. 274(3),1313-1319(1999).
2. 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(23),9383-9387(1990).
3. Basu, S. Metabolism of 8-iso-prostaglandin F FEBS Lett. 428(112),32-36(1998).
4. Cranshaw, J.H., Evans, T.W., and Mitchell, J.A. Charcterization of the effects of isoprostanes on platelet aggregation in human whole blood Br. J. Pharmacol. 132,1699-1706(2001).
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