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5-trans Prostaglandin E₂

Cayman Chemical Item Number 14210

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

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

See more	Prostaglandins (513)

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_2α. 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	trans-Dinoprostone 5,6-trans PGE2
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	Copy SMILES to clipboard CCCCCC(O)/C=C/[C@H]1C(O)CC(=O)C1C\C=C\CCCC(=O)O

Background Reading

Lohmus, M., Vahemets, A., Järving, I., et al. Preparative separation of natural prostaglandins E. Preparative Chromatography 1 279-300 (1991).

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).

Brookes, L.G., and Marshall, R.C. The effects of some prostaglandins on respiration in the rabbit. J Pharm Pharmacol 26, Suppl. 80P-81P (1974).

Blair, I.A., Hensby, C.N., and MacDermot, J. Prostacyclin-dependent activation of adenylate cyclase in a neuronal somatic cell hybrid: Prostanoid structure-activity relationships. Br J Pharmacol 69 519-525 (1980).

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_2α. J Am Chem Soc 94 2124 (1972).

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).

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).

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

Size	Price	Quantity	Subtotal
1 mg	$46.00		$0.00
5 mg	$207.00		$0.00
10 mg	$368.00		$0.00
100 mg	$2,760.00		$0.00
Bulk	Contact
		Cart Total	$0.00

Pricing updated 2012-02-12. Prices are subject to change without notice.

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Related Products

Prostaglandin E₁

Prostaglandin E₂

Prostaglandin E₂-d₉

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5-trans Prostaglandin E2