ChemicalBook Product Catalog Pharmaceutical intermediates Bulk Drug Intermediates 13,14-Dihydro-15-keto prostaglandin E2

13,14-Dihydro-15-keto prostaglandin E2

Product Name13,14-Dihydro-15-keto prostaglandin E2
CAS363-23-5
MFC20H32O5
MW352.47
EINECS
MOL File363-23-5.mol

Chemical Properties

Boiling point	538.1±45.0 °C(Predicted)
Density	1.086±0.06 g/cm3(Predicted)
storage temp.	−20°C
solubility	DMF: >100 mg/ml DMSO: >100 mg/ml Ethanol: >100 mg/mlPBS (pH 7.2): >5 mg/ml
form	Liquid
pka	4.75±0.10(Predicted)
color	Colorless to light yellow

Safety Information

Hazard Codes	F,Xn,Xi
Risk Statements	11-20/21/22-36/37/38-67-66-36
Safety Statements	16-26-36
RIDADR	UN 1231 3/PG 2
WGK Germany	3

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Description

13,14-dihydro-15-keto Prostaglandin E₂ (13,14-dihydro-15-keto PGE₂) is a metabolite of PGE₂ and the primary PGE₂ metabolite in plasma. It is formed from PGE₂ via a 15-keto PGE₂ intermediate by 15-oxo-PG Δ¹³ reductase. Unlike PGE₂, 13,14-dihydro-15-keto PGE₂ does not bind effectively to the PGE₂ receptors EP₂ and EP₄ expressed in CHO cells (K_is = 12 and 57 μM, respectively) or induce adenylate cyclase activity in the same cells (EC₅₀s = >18 and >38 μM, respectively). Levels of 13,14-dihydro-15-keto PGE₂ are increased in the plasma of women in the third trimester of pregnancy and in women during and immediately after labor and delivery. Levels of 13,14-dihydro-15-keto PGE₂ levels are decreased in tumor tissue compared to adjacent non-cancerous tissue isolated from patients with non-small cell lung cancer (NSCLC).

Uses

13,14-Dihydro-15-ketoPGE2 is a primary metabolite of PGE2 in plasma.

Definition

ChEBI: The 13,14-dihydro derivative of 15-oxo-prostaglandin E2.

References

[1] P. HUSSLEIN H. S. Concentration of 13,14-dihydro-15-keto-prostaglandin E2 in the maternal peripheral plasma during labour of spontaneous onset[J]. Bjog-An International Journal of Obstetrics and Gynaecology, 1984, 91 3: 228-231. DOI: 10.1111/j.1471-0528.1984.tb04757.x
[2] DUNCAN HUGHES. NAD+-dependent 15-hydroxyprostaglandin dehydrogenase regulates levels of bioactive lipids in non-small cell lung cancer.[J]. Cancer prevention research (Philadelphia, Pa.), 2008, 1 4: 241-249. DOI: 10.1158/1940-6207.capr-08-0055
[3] JOVANA MARIC PHD , PHD Gerd G M Nerea Ferreirós PhD, PHD Danielle F M, et al. Cytokine-induced endogenous production of prostaglandin D2 is essential for human group 2 innate lymphoid cell activation[J]. Journal of Allergy and Clinical Immunology, 2019, 143 6: Pages 2202-2214.e5. DOI: 10.1016/j.jaci.2018.10.069
[4] M. HAMBERG B S. On the Metabolism of Prostaglandins E1 and E2 in Man[J]. Journal of Biological Chemistry, 1971, 246 1: 6713-6721. DOI: 10.1016/s0021-9258(19)45905-x
[5] N. NISHIGAKI A I M Negishi. Two Gs-coupled prostaglandin E receptor subtypes, EP2 and EP4, differ in desensitization and sensitivity to the metabolic inactivation of the agonist.[J]. Molecular Pharmacology, 1996, 146 1: 1031-1037. DOI: 10.1254/fpj.108.supplement_65
[6] DAVID MERIWETHER. Apolipoprotein A-I mimetics mitigate intestinal inflammation in COX2-dependent inflammatory bowel disease model.[J]. Journal of Clinical Investigation, 2019, 129 9: 3670-3685. DOI: 10.1172/jci123700

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