A metabolite of 8-iso PGF2α with vasoconstrictor activity
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Parent Compound(s)
163508-iso Prostaglandin F2α
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8-iso-15-keto Prostaglandin F2α

Item No. 16390

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9α,11α-dihydroxy-15-oxo-(8β)-prosta-5Z,13E-dien-1-oic acid
CAS Number
191919-01-4
Synonyms
  • 8-epi-15-keto PGF2α
  • 8-iso-15-keto PGF2α
Molecular Formula
C20H32O5
Formula Weight
352.5
Purity
≥95%
Formulation (Request formulation change)
A 1 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
10 mM Na2CO3: >6.5 mg/mlDMF: >100 mg/mlDMSO: >100 mg/mlEthanol: >100 mg/mlPBS pH 7.2: >10 mg/ml
λmax
230 nm
SMILES
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
InChI=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
LOLJEILMPWPILA-RLXHZABYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    8-iso-15-keto Prostaglandin F2α (8-iso-15-keto PGF2α) is a metabolite of the isoprostane 8-iso PGF2α in rabbits, monkeys, and humans. 8-isoprostane (8-iso PGF2α) is a prostaglandin-like product of non-specific lipid peroxidation.1 In both humans and monkeys, exogenously infused 8-iso PGF2α 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 PGF2α is infused into rabbits.3 Early in the infusion (within 1-2 minutes) 8-iso -15-keto PGF2α was a major component of the metabolite profile, which was comprised mostly of unmetabolized 8-iso PGF2α. 8-iso -15-keto PGF2α is a vasoconstrictor when tested on the rat isolated thoracic aorta, acting via the TP (thromboxane) receptor.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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(23), 9383-9387 (1990).

    2. Chiabrando, C., Valagussa, A., Rivalta, C., et al. Identification and measurement of endogenous β-oxidation metabolites of 8-epi-prostaglandin F2α. The Journal of Biological Chemisty 274(3), 1313-1319 (1999).

    3. Basu, S. Metabolism of 8-iso-prostaglandin F2α. FEBS Lett. 428(112), 32-36 (1998).

    4. Cracowski, J.L., Camus, L., Durand, T., et al. Response of rat thoracic aorta to F2-isoprostane metabolites. J. Cardiovasc. Pharmacol. 39(3), 396-403 (2002).