A metabolite of 8-iso PGF2α
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Parent Compound(s)
163508-iso Prostaglandin F2α
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2,3-dinor-8-iso Prostaglandin F2α

Item No. 16290

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3Z)-5-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-1-octen-1-yl]cyclopentyl]-3-pentenoic acid
CAS Number
221664-05-7
Synonyms
  • 2,3-dinor-iPF2α-III
  • 2,3-dinor-8-iso PGF2α
Molecular Formula
C18H30O5
Formula Weight
326.4
Purity
≥95%
Formulation (Request formulation change)
A 100 µg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: >100 mg/mlDMSO: >100 mg/mlEthanol: >100 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
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
InChI=1S/C18H30O5/c1-2-3-4-7-13(19)10-11-15-14(16(20)12-17(15)21)8-5-6-9-18(22)23/h5-6,10-11,13-17,19-21H,2-4,7-9,12H2,1H3,(H,22,23)/b6-5-,11-10+/t13-,14-,15+,16-,17+/m0/s1
InChi Key
IDKLJIUIJUVJNR-JSEKUSAISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 µg

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    100 µg

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    Product Description

    8-iso Prostaglandin F2α (8-iso PGF2α; 8-isoprostane) is a prostaglandin-like product of non-specific lipid peroxidation.1 2,3-dinor-8-iso PGF2α is a metabolite of 8-iso PGF2α in humans and rats.2 In these species, exogenously infused 8-iso PGF2α is converted to 2,3-dinor-8-iso PGF1α and (2,3-dinor-8-iso PGF2α.2,3 Rat hepatocytes further metabolize 8-iso PGF2α to another β-oxidation product, 2,3,4,5-tetranor-8-iso PGF2α.2 2,3-dinor-8-iso PGF2α is present in normal human urine at concentrations of 200-300 pg/ml.2 Its concentration is increased in conditions of oxidative injury (for example, smoking), and correlates well with that of the parent isoprostane, 8-iso PGF2α.2

    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. Roberts, L.J., II, Moore, K.P., Zackert, W.E., et al. Identification of the major urinary metabolite of the F2-isoprostane 8-iso-prostaglandin F2α in humans. The Journal of Biological Chemisty 271(34), 20617-20620 (1996).

    Product Citations

    Sasaki, A., Fukuda, H., Shiida, N., et al. Determination of ω-6 and ω-3 PUFA metabolites in human urine samples using UPLC/MS/MS. Anal. Bioanal. Chem. 407(6), 1625-1639 (2015).