5-trans-Prostaglandin E2

Base Information

• Chemical Name: 5-trans-Prostaglandin E2
• CAS No.: 36150-00-2
• Molecular Formula: C₂₀H₃₂O₅
• Molecular Weight: 352.471
• Hs Code.: 2937500000
• UNII: 6V30L285LP
• DSSTox Substance ID: DTXSID40189722
• Nikkaji Number: J17.783K
• Wikidata: Q27265557
• Metabolomics Workbench ID: 2490
• Mol file: 36150-00-2.mol

Synonyms:5-trans-Prostaglandin E2;36150-00-2;5-trans Prostaglandin E2;trans-Dinoprostone;5-trans-PGE2;5,6-trans-Dinoprostone;5,6-trans-PGE2;Alprostadil impurity H [EP];UNII-6V30L285LP;6V30L285LP;(E)-7-((1R,2R,3R)-3-Hydroxy-2-((E)-(3S)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoic acid;Dinoprostone specified impurity C [EP];9-oxo-11R,15S-dihydroxy-5E,13E-prostadienoic acid;Dinoprostone impurity, 5,6-trans-dinoprostone- [USP];Prosta-5,13-dien-1-oic acid, 11,15-dihydroxy-9-oxo-, (5E,11alpha,13E,15S)-;(E)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid;Dinoprostone impurity C;5,6-trans PGE2;PGE2, 5,6-trans;(5E)-PROSTAGLANDIN E2;SCHEMBL23352614;DTXSID40189722;7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]-5-heptenoic acid;HMS3648F17;BDBM50213982;LMFA03010148;PDSP2_001531;PD021141;ALPROSTADIL IMPURITY H [EP IMPURITY];DINOPROSTONE IMPURITY C [EP IMPURITY];SR-01000946421;SR-01000946421-1;Q27265557;9-Oxo-11|A,15S-dihydroxy-prosta-5E,13E-dien-1-oic acid;PROSTA-5,13-DIEN-1-OIC ACID, 11,15-DIHYDROXY-9-OXO-, (5E,11.ALPHA.,13E,15S)-;(5E)-7-((1R,2R,3R)-3-HYDROXY-2-((1E,3S)-3-HYDROXYOCT-1-ENYL)-5-OXOCYCLOPENTYL)HEPT-5-ENOIC ACID ((5E)-PROSTAGLANDIN E2);(E)-7-((1R,2R,3R)-3-hydroxy-2-((S,E)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoic acid

Chemical Property of 5-trans-Prostaglandin E2

Chemical Property:

• PSA: 94.83000
• LogP: 3.25110
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 352.22497412
• Heavy Atom Count: 25
• Complexity: 469

Purity/Quality:

99%, ^*data from raw suppliers

5-trans-ProstaglandinE2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC1C(CC(=O)C1CC=CCCCC(=O)O)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1C/C=C/CCCC(=O)O)O)O
• Uses: 5-trans-Prostaglandin E2 is used as a substance for the isolation of new naturally occuring prostaglandin 5-trans-PGA2, in the synthesis of 5-trans-PGE2, 5-trans-PGF2a and their 5,6-trans isomers.

Technology Process of 5-trans-Prostaglandin E2

There total 26 articles about 5-trans-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:

(5Z,8R,9R,11S,12S,13E,15R)-11,15-bis-(tert-butyldimethylsilyloxy)-9-oxoprosta-5,13-dienoic acid (303015-41-0) → ent-prostaglandin E2 (363-24-6,13164-28-8,22230-04-2,27415-25-4,31660-13-6,31660-17-0,36150-00-2,37495-69-5,37785-90-3,38310-90-6,38873-82-4,39265-67-3,39648-42-5,54324-09-3,54324-10-6,57759-80-5,57759-81-6,63179-97-5,65026-02-0,65085-69-0,70051-84-2,85548-91-0) + ent-15-E2t-isoprostane

Guidance literature:

(5Z,8R,9R,11S,12S,13E,15R)-11,15-bis-(tert-butyldimethylsilyloxy)-9-oxoprosta-5,13-dienoic acid; With pyridine; hydrogen fluoride; In tetrahydrofuran; water; acetonitrile; at 20 ℃; for 6h;

With potassium acetate; In methanol; at 20 ℃; for 96h;

DOI:10.1016/S0040-4020(00)00531-7

Reference yield:

(Z)-7-[(1R,2S,3S,5R)-5-Acetoxy-3-hydroxy-2-((E)-(R)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid ethyl ester (214748-78-4) → ent-prostaglandin E2 (363-24-6,13164-28-8,22230-04-2,27415-25-4,31660-13-6,31660-17-0,36150-00-2,37495-69-5,37785-90-3,38310-90-6,38873-82-4,39265-67-3,39648-42-5,54324-09-3,54324-10-6,57759-80-5,57759-81-6,63179-97-5,65026-02-0,65085-69-0,70051-84-2,85548-91-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 82 percent / imidazole; DMAP / CH₂Cl₂ / 24 h / 20 °C

2.1: 92 percent / LiOH*H₂O / tetrahydrofuran; H₂O; methanol / 24 h / 20 °C

3.1: 95 percent / Dess-Martin periodinate / CH₂Cl₂ / 20 h / 20 °C

4.1: HF; pyridine / H₂O; tetrahydrofuran; acetonitrile / 6 h / 20 °C

4.2: KOAc / methanol / 96 h / 20 °C

With pyridine; 1H-imidazole; dmap; lithium hydroxide; hydrogen fluoride; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 1.1: Substitution / 2.1: Hydrolysis / 3.1: Oxidation / 4.1: Hydrolysis / 4.2: Isomerization;

DOI:10.1016/S0040-4020(00)00531-7

Reference yield:

(5Z,8R,9R,11S,12S,13E,15R)-11,15-bis-(tert-butyldimethylsilyloxy)-9-hydroxyprosta-5,13-dienoic acid (303015-43-2) → ent-prostaglandin E2 (363-24-6,13164-28-8,22230-04-2,27415-25-4,31660-13-6,31660-17-0,36150-00-2,37495-69-5,37785-90-3,38310-90-6,38873-82-4,39265-67-3,39648-42-5,54324-09-3,54324-10-6,57759-80-5,57759-81-6,63179-97-5,65026-02-0,65085-69-0,70051-84-2,85548-91-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / Dess-Martin periodinate / CH₂Cl₂ / 20 h / 20 °C

2.1: HF; pyridine / H₂O; tetrahydrofuran; acetonitrile / 6 h / 20 °C

2.2: KOAc / methanol / 96 h / 20 °C

With pyridine; hydrogen fluoride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; water; acetonitrile; 1.1: Oxidation / 2.1: Hydrolysis / 2.2: Isomerization;

DOI:10.1016/S0040-4020(00)00531-7

upstream raw materials:

(5Z,8R,9R,11S,12S,13E,15R)-11,15-bis-(tert-butyldimethylsilyloxy)-9-oxoprosta-5,13-dienoic acid

(Z)-7-[(1R,2S,3S,5R)-5-Acetoxy-3-hydroxy-2-((E)-(R)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid ethyl ester

(5Z,8R,9R,11S,12S,13E,15R)-11,15-bis-(tert-butyldimethylsilyloxy)-9-hydroxyprosta-5,13-dienoic acid

ethyl (5Z,8R,9R,11S,12S,13E,15R)-9-acetoxy-11,15-bis-(tert-butyldimethylsilyloxy)prosta-5,13-dienoate

Downstream raw materials:

(+/-)-prostaglandin E₂ methyl ester

Refernces

• 1、 -. "Racemic prostaglandins of the 2-series and analogs thereof". . . Retrieved 2008/06/13.
• 2、 Bundy,Daniels,Lincoln,Pike. "Isolation of a new naturally occurring prostaglandin, 5-trans-PGA 2 . Synthesis of 5-trans-PGE 2 and 5-trans-PGF 2a .". . p. 2124 - 2124. Retrieved 2007/10/06.