prostaglandin E3

Base Information

• Chemical Name: prostaglandin E3
• CAS No.: 802-31-3
• Molecular Formula: C₂₀H₃₀O₅
• Molecular Weight: 350.455
• UNII: ZED6SBL53S
• ChEMBL ID: CHEMBL2074717
• DSSTox Substance ID: DTXSID301045731
• Metabolomics Workbench ID: 2478
• NCI Thesaurus Code: C121971
• Nikkaji Number: J14.036H
• Wikidata: Q15708280
• Wikipedia: Prostaglandin_E3
• Mol file: 802-31-3.mol

Synonyms:delta(17)-PGE1;delta(17)-prostaglandin E1;PGE1, delta(17)-;PGE3;prostaglandin E3

Chemical Property of prostaglandin E3

Chemical Property:

• Vapor Pressure: 5.86E-14mmHg at 25°C
• Melting Point: 84.5-85.5 °C
• Boiling Point: 541 °C at 760 mmHg
• PKA: 4.75±0.10(Predicted)
• Flash Point: 295 °C
• PSA: 94.83000
• Density: 1.166 g/cm³
• LogP: 3.02710
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 350.20932405
• Heavy Atom Count: 25
• Complexity: 506

Purity/Quality:

98%Min ^*data from raw suppliers

Prostaglandin E3 ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC(C=CC1C(CC(=O)C1CC=CCCCC(=O)O)O)O
• Isomeric SMILES: CC/C=C\C[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O)O
• Uses: Prostaglandin E3 (PGE3) is formed via the cyclooxygenase (COX) metabolism of eicosapentaenoic acid. In human ocular tissue, it comprises 2.4% of the COX products formed. When applied to the eyes of a rabbit, a 1 μg dose of PGE3 decreases intraocular pressure from 21 mmHg to about 17 mmHg.

Technology Process of prostaglandin E3

There total 7 articles about prostaglandin E3 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: 78.0%

(Z)-7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(1E,5Z)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-octa-1,5-dienyl]-5-oxo-cyclopentyl}-hept-5-enoic acid (127268-97-7) → Prostaglandin E3 (802-31-3)

Guidance literature:

With hydrogen fluoride; In acetonitrile; for 0.666667h; Ambient temperature;

DOI:10.1016/S0040-4039(00)99365-1

Reference yield:

(4R)-2-(N,N-diethylamino)methyl-4-(t-butyldimethylsiloxy)-cyclopent-2-en-1-ol (117254-07-6) → Prostaglandin E3 (802-31-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) n-BuLi, (2-thienyl)Cu(CN)Li / 1.) THF, -78 deg C; 2.) THF, -78 to 0 deg C, 1 h

2: 80 percent / t-BuLi, (2-thienyl)Cu(CN)Li / tetrahydrofuran; diethyl ether; pentane / 1 h / -78 deg C up to 0 deg C

3: 86 percent / PPTS / propan-2-ol; diethyl ether / 5 h / Ambient temperature

4: 79 percent / Jones reagent / acetone; diethyl ether / 0.5 h / 0 °C

5: 78 percent / aq. HF / acetonitrile / 0.67 h / Ambient temperature

With n-butyllithium; jones reagent; hydrogen fluoride; tert.-butyl lithium; thien-2-yl(cyano)copper lithium; pyridinium p-toluenesulfonate; In tetrahydrofuran; diethyl ether; isopropyl alcohol; acetone; acetonitrile; pentane;

DOI:10.1016/S0040-4039(00)99365-1

Reference yield:

tert-Butyl-dimethyl-[(Z)-(S)-1-((E)-2-tributylstannanyl-vinyl)-hex-3-enyloxy]-silane (127268-93-3) → Prostaglandin E3 (802-31-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) n-BuLi, (2-thienyl)Cu(CN)Li / 1.) THF, -78 deg C; 2.) THF, -78 to 0 deg C, 1 h

2: 80 percent / t-BuLi, (2-thienyl)Cu(CN)Li / tetrahydrofuran; diethyl ether; pentane / 1 h / -78 deg C up to 0 deg C

3: 86 percent / PPTS / propan-2-ol; diethyl ether / 5 h / Ambient temperature

4: 79 percent / Jones reagent / acetone; diethyl ether / 0.5 h / 0 °C

5: 78 percent / aq. HF / acetonitrile / 0.67 h / Ambient temperature

With n-butyllithium; jones reagent; hydrogen fluoride; tert.-butyl lithium; thien-2-yl(cyano)copper lithium; pyridinium p-toluenesulfonate; In tetrahydrofuran; diethyl ether; isopropyl alcohol; acetone; acetonitrile; pentane;

DOI:10.1016/S0040-4039(00)99365-1

upstream raw materials:

(Z)-7-{(1R,2R,3R,5S)-5-Hydroxy-3-(tetrahydro-pyran-2-yloxy)-2-[(1E,5Z)-(S)-3-(tetrahydro-pyran-2-yloxy)-octa-1,5-dienyl]-cyclopentyl}-hept-5-enoic acid

(Z)-7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(1E,5Z)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-octa-1,5-dienyl]-5-oxo-cyclopentyl}-hept-5-enoic acid

(4R)-2-(N,N-diethylamino)methyl-4-(t-butyldimethylsiloxy)-cyclopent-2-en-1-ol

tert-Butyl-dimethyl-[(Z)-(S)-1-((E)-2-tributylstannanyl-vinyl)-hex-3-enyloxy]-silane

Downstream raw materials:

(Z)-7-[(1R,2R,3R)-3-Hydroxy-2-((1E,5Z)-(S)-3-hydroxy-octa-1,5-dienyl)-5-oxo-cyclopentyl]-hept-5-enoic acid biphenyl-4-yloxycarbonylmethyl ester

Prostaglandin E(3)-p-phenylbenzylester

(Z)-7-[(1R,2R,3R)-3-Hydroxy-2-((1E,5Z)-(S)-3-hydroxy-octa-1,5-dienyl)-5-oxo-cyclopentyl]-hept-5-enoic acid 2-(2,5-dimethoxy-phenyl)-2-oxo-ethyl ester

Refernces

• 1、 Corey,Shirahama,Yamamoto,Terashima,Venkateswarlu,Schaaf. "Stereospecific total synthesis of prostaglandins E3 and F3 alpha.". . p. 1490 - 1491. Retrieved 2007/10/16.