5-trans Prostaglandin E2

Cayman Chemical Item Number 14210

5,6-trans PGE2; trans-Dinoprostone (CAS 36150-00-2)

5-trans Prostaglandin E2 (CAS 36150-00-2)

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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

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-PGF. J Am Chem Soc 94 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 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 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).

Synonyms
  • 5,6-trans PGE2
  • trans-Dinoprostone
Formal Name 9-​oxo-​11α,​15S-​dihydroxy-​prosta-​5E,​13E-​dien-​1-​oic acid
CAS Number 36150-00-2
Molecular Formula C20H32O5
Formula Weight 352.5
Formulation A crystalline solid
Purity >98%
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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CCCCCC(O)​/C=C/[C@H]​1C(O)​CC(=O)​C1C\C=C\CCCC(=O)​O
InCHI Code
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​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
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XEYBRNLFEZDVAW-BRNHSORCSA-N

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5-trans Prostaglandin E2 is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $51.00 $0.00
5 mg $230.00 $0.00
10 mg $408.00 $0.00
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Pricing updated 2014-04-24. Prices are subject to change without notice.

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Cayman Chemical was formed over thirty years ago by demonstrating the value of naturally growing gorgonian corals as a renewable, economically viable source of prostaglandins. Today we operate our business knowing that we owe our start to the renewable resources our environment had provided. As Cayman Chemical continues to grow we consistently evaluate our business processes to ensure we are operating at the highest environmental standards.

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