A stable, base-catalyzed transformation product of 13,14-dihydro-15-keto PGE2
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Bicyclo Prostaglandin E2

Item No. 14530

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5Z)-7-[(1R,3aS,7aS)-4-butyloctahydro-2,5-dioxo-1H-inden-1-yl]-5-heptenoic acid
CAS Number
109826-53-1
Synonyms
  • Bicyclo PGE2
Molecular Formula
C20H30O4
Formula Weight
334.5
Purity
≥98%
Formulation (Request formulation change)
A 10 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: >25 mg/mlDMSO: >25 mg/mlEthanol: >30 mg/mlPBS (pH 7.2): >1.4 mg/ml
SMILES
CCCCC1([H])C(CC[C@H]([C@H]2C/C=C\CCCC(O)=O)[C@@H]1CC2=O)=O
InChi Code
InChI=1S/C20H30O4/c1-2-3-8-16-17-13-19(22)15(14(17)11-12-18(16)21)9-6-4-5-7-10-20(23)24/h4,6,14-17H,2-3,5,7-13H2,1H3,(H,23,24)/b6-4-/t14-,15-,16?,17+/m1/s1
InChi Key
CGCZPIJMGKLVTQ-PAJBVNRRSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Bicyclo prostaglandin E2 (Bicyclo PGE2) is a stable breakdown product of PGE2 (Item No. 14010) and 13,14-dihydro-15-keto PGE2 (Item No. 14650). Bicyclo PGE2 is a stable, base-catalyzed transformation product of 13,14-dihydro-15-keto PGE2. 13,14-dihydro-15-keto PGE2 itself is a metabolite of PGE2 found in human plasma at a median level of 20-25 pg/ml.1,2 Due to the inherent instability of 13,14-dihydro-15-keto PGE2, it is advisable to quantify it as bicyclo PGE2 to estimate PGE2 biosynthesis or metabolism in vivo.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hamberg, M., and Samuelsson, B. On the metabolism of prostaglandins E1 and E2 in man. The Journal of Biological Chemisty 246(22), 6713-6721 (1971).

    2. Leonhardt, A., Krauss, M., Gieler, U., et al. In vivo formation of prostaglandin E1 and prostaglandin E2 in atopic dermatitis. Br. J. Dermatol. 136(3), 337-340 (1997).

    3. Murphy, R.C., and Fitzgerald, G.A. Current approaches to estimation of eicosanoid formation in vivo. Adv. Prostaglandin Thromboxane Leukot. Res. 22, 341-348 (1994).

    4. Granström, E., Hamberg, M., Hansson, G., et al. Chemical instability of 15-keto-13,14-dihydro-PGE2: The reason for low assay reliability. Prostaglandins 19(6), 933-945 (1980).