6-ketoprostaglandin E1

Base Information

• Chemical Name: 6-ketoprostaglandin E1
• CAS No.: 67786-53-2
• Molecular Formula: C20H32O6
• Molecular Weight: 368.47
• European Community (EC) Number: 688-563-4
• ChEMBL ID: CHEMBL138482
• DSSTox Substance ID: DTXSID701318279
• Metabolomics Workbench ID: 2382
• Nikkaji Number: J428.385F
• Wikidata: Q27103600
• Mol file: 67786-53-2.mol

Synonyms:6-keto-PGE1;6-keto-prostaglandin E1;6-ketoprostaglandin E1;6-oxo-PGE1;6-oxoprostaglandin E1

Chemical Property of 6-ketoprostaglandin E1

Chemical Property:

• Vapor Pressure: 8.1E-16mmHg at 25°C
• Boiling Point: 579°C at 760 mmHg
• Flash Point: 318°C
• PSA: 111.90000
• Density: 1.187g/cm³
• LogP: 2.65410
• Storage Temp.: −20°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 368.21988874
• Heavy Atom Count: 26
• Complexity: 499

Purity/Quality:

6-keto Prostaglandin E1 ≥99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC1C(CC(=O)C1CC(=O)CCCCC(=O)O)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CC(=O)CCCCC(=O)O)O)O
• Uses: 6-Keto-PGE1 is a metabolite of prostacyclin(P839060). Prostacyclin is an Eicosanoid which prevents the formation of platelet plugs and is an effective vasodilator.

Technology Process of 6-ketoprostaglandin E1

There total 10 articles about 6-ketoprostaglandin E1 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: 89.0%

6-oxo-PGE1 methyl ester (67786-49-6) → 6-keto prostaglandin E1 (67786-53-2)

Guidance literature:

for 18h; Ambient temperature; hydrolysis porcine liver esterase;

DOI:10.1016/S0040-4039(01)91266-3

Reference yield:

Methyl 6-nitro-6-heptenoate (88462-11-7) → 6-keto prostaglandin E1 (67786-53-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) t-butyllithium; 2) copper(I)iodide, tributylphosphine

2: 1) triphenylphosphine; 2) 25percent aq. TiCl₃, NH₄OAc / 1) THF, rt., 15 min; 2) THF-water-MeOH, rt., 5 h

3: 92 percent / hydrogen fluoride-pyridine / acetonitrile / 1.5 h / Ambient temperature

4: 89 percent / porcine liver esterase, phosphate buffer solution (pH=8) / acetone; H₂O / 20 h / Ambient temperature

With porcine liver esterase; copper(l) iodide; titanium(III) chloride; tributylphosphine; phosphate buffer solution; ammonium acetate; tert.-butyl lithium; pyridine hydrogenfluoride; triphenylphosphine; In water; acetone; acetonitrile;

DOI:10.1016/S0040-4020(01)90018-3

Reference yield:

methyl 6-bromohexanoate (14273-90-6) → 6-keto prostaglandin E1 (67786-53-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 51 percent / sodium nitrite, phloroglucinol / dimethylsulfoxide / 20 h / Ambient temperature

2: 1) 3N sodium hydroxide; 3) acetic acid / 1) H₂O, 0 deg C, 3 h; 2) H₂O, 0 deg C, 5 h; 3) H₂O, room temp., 20 h

3: 79 percent / mesyl chloride, triethylamine / CH₂Cl₂ / 1 h / 0 °C

4: 1) t-butyllithium; 2) copper(I)iodide, tributylphosphine

5: 1) triphenylphosphine; 2) 25percent aq. TiCl₃, NH₄OAc / 1) THF, rt., 15 min; 2) THF-water-MeOH, rt., 5 h

6: 92 percent / hydrogen fluoride-pyridine / acetonitrile / 1.5 h / Ambient temperature

7: 89 percent / porcine liver esterase, phosphate buffer solution (pH=8) / acetone; H₂O / 20 h / Ambient temperature

With porcine liver esterase; sodium hydroxide; copper(l) iodide; titanium(III) chloride; 3,5-dihydroxyphenol; tributylphosphine; phosphate buffer solution; ammonium acetate; tert.-butyl lithium; pyridine hydrogenfluoride; acetic acid; methanesulfonyl chloride; triethylamine; triphenylphosphine; sodium nitrite; In dichloromethane; water; dimethyl sulfoxide; acetone; acetonitrile;

DOI:10.1016/S0040-4020(01)90018-3

upstream raw materials:

6-oxo-PGE₁ methyl ester

methyl 6-bromohexanoate

Methyl 6-nitro-6-heptenoate

11,15-O-Bis(tert-butyldimethylsilyl)-6-nitro-PGE₁ methyl ester

Refernces

• 1、 Tanaka, Toshio,Hazato, Atsuo,Bannai, Kiyoshi,Okamura, Noriaki,Sugiura, Satoshi,et al.. "Nitro-Olefin Trapping Reactions of Enolates In Situ Generated by Conjugate Addition Reaction: Short Syntheses of PGE1, 6-Oxo-PGE1, 6-Oxo-PGF1α, and PGI2". . p. 813 - 824. Retrieved 2007/10/02.