tetranor-PGEM

Base Information

• Chemical Name: tetranor-PGEM
• CAS No.: 24769-56-0
• Molecular Formula: C₁₆H₂₄O₇
• Molecular Weight: 328.362
• Hs Code.: 2918990090
• DSSTox Substance ID: DTXSID50947678
• Nikkaji Number: J1.264.716F
• Wikidata: Q27144287
• Metabolomics Workbench ID: 2398
• Mol file: 24769-56-0.mol

Synonyms:11 alpha-hydroxy-9,15-dioxo-2,3,4,5,20-pentanor-19-carboxyprostanoic acid;HDOPNP;PGE-MUM

Chemical Property of tetranor-PGEM

Chemical Property:

• Vapor Pressure: 4.35E-18mmHg at 25°C
• Boiling Point: 622.2°Cat760mmHg
• PKA: 4.61±0.10(Predicted)
• Flash Point: 344.1°C
• PSA: 128.97000
• Density: 1.266g/cm³
• LogP: 1.41160
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 328.15220310
• Heavy Atom Count: 23
• Complexity: 457

Purity/Quality:

98%Min ^*data from raw suppliers

PGE-M ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C1=O)CCC(=O)O)CCC(=O)CCCCC(=O)O)O
• Isomeric SMILES: C1[C@H]([C@@H]([C@H](C1=O)CCC(=O)O)CCC(=O)CCCCC(=O)O)O
• Description: tetranor-PGEM is the major urinary metabolite of PGE1 and PGE2, and is used as a marker of PGE2 biosynthesis. About 15% of an infused dose of PGE2 appears as this metabolite in the urine of humans. Normal healthy males excrete 7-40 μg of tetranor-PGEM over a 24-hour period.
• Uses: The major urinary metabolite of Prostaglandin E2 (P838610).

Technology Process of tetranor-PGEM

There total 7 articles about tetranor-PGEM 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: 90.0%

dibenzyl (1,2,3,4-tetranor)-9,15-dioxo-11-hydroxyprostanedioate → tetranor prostaglandinEmetabolite (24769-56-0)

Guidance literature:

With palladium on carbon; hydrogen; In ethanol; at 20 ℃; for 0.666667h;

DOI:10.1016/j.tet.2009.05.059

Reference yield:

C28H48O8Si → tetranor prostaglandinEmetabolite (24769-56-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium tetrahydroborate / ethanol / 0.67 h / Inert atmosphere

1.2: 24 h / 20 °C / Inert atmosphere

1.3: Inert atmosphere

2.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / Inert atmosphere

3.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

4.1: pyridine; hydrogen fluoride / water; acetonitrile / 7 h / Inert atmosphere

5.1: palladium on carbon; hydrogen / ethanol / 0.67 h / 20 °C

With pyridine; sodium tetrahydroborate; palladium on carbon; hydrogen fluoride; hydrogen; potassium carbonate; Dess-Martin periodane; In ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.tet.2009.05.059

Reference yield:

dibenzyl (1,2,3,4-tetranor)-9,15-dioxo-11-dimethyl-(dimethylethyl)silyloxyprostanedioate → tetranor prostaglandinEmetabolite (24769-56-0)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine; hydrogen fluoride / water; acetonitrile / 7 h / Inert atmosphere

2: palladium on carbon; hydrogen / ethanol / 0.67 h / 20 °C

With pyridine; palladium on carbon; hydrogen fluoride; hydrogen; In ethanol; water; acetonitrile;

DOI:10.1016/j.tet.2009.05.059

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