An impurity in commercial lots of PGE1
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Isomer(s)
14010Prostaglandin E2
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5-trans Prostaglandin E2

Item No. 14210

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
11α,15S-dihydroxy-9-oxo-prosta-5E,13E-dien-1-oic acid
CAS Number
36150-00-2
Synonyms
  • trans-Dinoprostone
  • 5,6-trans PGE2
Molecular Formula
C20H32O5
Formula Weight
352.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: >100 mg/mlDMSO: >100 mg/mlEthanol: >100 mg/mlPBS (pH 7.2): >5 mg/ml
SMILES
O=C1[C@H](C/C=C/CCCC(O)=O)[C@@H](/C=C/[C@@H](O)CCCCC)[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/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4+,13-12+/t15-,16+,17+,19+/m0/s1
InChi Key
XEYBRNLFEZDVAW-BRNHSORCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

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    Product Description

    5-trans PGE2 occurs naturally in some gorgonian corals and is a common impurity in commercial lots of PGE1.1 It is 18 times more potent than PGE2 in activating adenylate cyclase in NCB-20 cell homogenates.2 5-trans PGE2 accelerates fibrinolysis by enhancing plasminogen activation mediated by tissue-type plasminogen activator.3 It also inhibits platelet aggregation in human PRP with an IC50 of 180 nM.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bundy, G.L., Schneider, W.P., Lincoln, F.H., et al. Isolation of a new naturally occurring prostaglandin, 5-trans-PGA2. Synthesis of 5-trans-PGE2 and 5-trans-PGF2α. J. Am. Chem. Soc. 94(6), 2124 (1972).

    2. Hensby, C.N., and MacDermot, J. Structure-activity relationships of prostanoids that activate adenylate cyclase of neuronal hybrid cells. Biochem. Soc. Trans. 7(6), 1302-1304 (1979).

    3. Shimokawa, M., Urano, T., and Kinoshita, T. trans-5-Prostaglandin E2 stimulates plasminogen activation by tissue-type plasminogen activator. Biochim. Biophys. Acta 1137(3), 317-320 (1992).

    4. Kobzar, G., Mardla, V., Järving, I., et al. Comparison of the inhibitory effect of E-prostaglandins in human and rabbit platelet-rich plasma and washed platelets. Comp. Biochem. Physiol. 106(2), 489-494 (1993).