15-keto-prostaglandin E2

Base Information

• Chemical Name: 15-keto-prostaglandin E2
• CAS No.: 26441-05-4
• Molecular Formula: C20H30O5
• Molecular Weight: 350.455
• UNII: 2S0F1FTK13
• ChEMBL ID: CHEMBL1447369
• DSSTox Substance ID: DTXSID401317991
• Metabolomics Workbench ID: 2396
• Nikkaji Number: J346.055J
• Wikidata: Q27098095
• Mol file: 26441-05-4.mol

Synonyms:15-keto-PGE2;15-keto-prostaglandin E2;15-ketoprostaglandin E2;15-ketoprostaglandin E2, (11alpha)-isomer;15-oxo-PGE2;9,15-dioxo-11-hydroxyprosta-5,13-dienoic acid

Chemical Property of 15-keto-prostaglandin E2

Chemical Property:

• Vapor Pressure: 1.19E-13mmHg at 25°C
• Refractive Index: 1.552
• Boiling Point: 534.4 °C at 760 mmHg
• PKA: 4.75±0.10(Predicted)
• Flash Point: 291 °C
• PSA: 91.67000
• Density: 1.144 g/cm³
• LogP: 3.45930
• Storage Temp.: −20°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 350.20932405
• Heavy Atom Count: 25
• Complexity: 506

Purity/Quality:

99% ^*data from raw suppliers

15-KetoProstaglandinE2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(=O)C=CC1C(CC(=O)C1CC=CCCCC(=O)O)O
• Isomeric SMILES: CCCCCC(=O)/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O
• Description: 15-keto Prostaglandin E2 (15-keto PGE2) is a metabolite of PGE2 (Item Nos. 14010) formed by 15-hydroxy prostaglandin dehydrogenase (15-PGDH). Unlike PGE2, 15-keto PGE2 does not bind effectively to the PGE2 receptors EP2 and EP4 expressed in CHO cells (Kis = 2.6 and 15 μM, respectively) or induce adenylate cyclase activity in the same cells (EC50s = 1.8 and >33 μM, respectively). However, it does bind to EP2 and EP4 in HEK cells expressing these receptors (IC50s = 0.117 and 2.82 μM, respectively), as well as induces cAMP formation (EC50s = 0.137 and 0.426 μM, respectively) and the transcriptional activity of β-catenin/TCF in the same cells. 15-keto PGE2 inhibits CD3-CD28-MHC-I-induced proliferation of isolated human CD4+ T cells in a concentration-dependent manner. It also reduces mortality in a mouse model of LPS-induced sepsis when administered at a dose of 15 mg/kg.15-keto PGE2 MaxSpec? standard is a quantitative grade standard of 15-keto PGE2 that has been prepared specifically for mass spectrometry or any application where quantitative reproducibility is required. The solution has been prepared gravimetrically and is supplied in a deactivated glass ampule sealed under argon. The concentration was verified by comparison to an independently prepared calibration standard. This 15-keto PGE2 MaxSpec? standard is guaranteed to meet identity, purity, stability, and concentration specifications and is provided with a batch-specific certificate of analysis. Ongoing stability testing is performed to ensure the concentration remains accurate throughout the shelf life of the product. Note: The amount of solution added to the vial is in excess of the listed amount. Therefore, it is necessary to accurately measure volumes for preparation of calibration standards. Follow recommended storage and handling conditions to maintain product quality.
• Uses: 15-keto Prostaglandin E2 (15-keto PGE2) is a metabolite of PGE2 formed by 15-hydroxy PGDH. In vivo, 15-keto PGE2 is essentially inactive. It has an attenuated affinity for the EP4 and EP2 receptors compared to PGE2 (Ki = 2,600-15,000 nM for the inhibition of PGE2 binding compared to a Kd = 1 nM for PGE2).[Cayman Chemical] 15-Keto Prostaglandin E2 is a lipid compound derived from arachidonic acid by the action of cyclooxygenases. Prostaglandins act locally as messenger molecules in a variety of physiological processes.

Technology Process of 15-keto-prostaglandin E2

There total 3 articles about 15-keto-prostaglandin E2 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

15-hydroperoxy-PGE2 → dinoprostone (363-24-6) + 15-Oxoprostaglandin E2 (26441-05-4,914804-63-0)

Guidance literature:

With methanol; sodium tetrahydroborate; at 37 ℃; for 24h; Temperature;

DOI:10.1002/anie.201910461

Reference yield:

dinoprostone (363-24-6) → 15-Oxoprostaglandin E2 (26441-05-4,914804-63-0)

Guidance literature:

With hydrogenchloride; nicotinamide adenine dinucleotide; 2-amino-2-hydroxymethyl-1,3-propanediol; 15-hydroxyprostaglandin dehydrogenase; In water; at 37 ℃; pH=7.5; Further Variations:; Catalysts; Kinetics; Enzyme kinetics;

DOI:10.1016/j.bmc.2006.06.030

Reference yield:

→ 15-Oxoprostaglandin E2 (26441-05-4,914804-63-0)

Guidance literature:

Verb. 1b, CrO3;

DOI:10.1021/jo00951a043

upstream raw materials:

dinoprostone

Refernces

• 1、 Jagusch, Hans,Werner, Markus,Werz, Oliver,Pohnert, Georg. "15-Hydroperoxy-PGE2: Intermediate in Mammalian and Algal Prostaglandin Biosynthesis". . p. 17641 - 17645. Retrieved 2019.