8-isoprostaglandin E2

Base Information

• Chemical Name: 8-isoprostaglandin E2
• CAS No.: 27415-25-4
• Molecular Formula: C₂₀H₃₂O₅
• Molecular Weight: 352.471
• UNII: W1ANC8Q5NW
• DSSTox Substance ID: DTXSID701024826
• Nikkaji Number: J838.387A
• Wikidata: Q27292182
• Metabolomics Workbench ID: 2819
• Mol file: 27415-25-4.mol

Synonyms:8-iso-PGE2;8-isoprostaglandin E2

Chemical Property of 8-isoprostaglandin E2

Chemical Property:

• Vapor Pressure: 1.89E-13mmHg at 25°C
• Boiling Point: 530.1°Cat760mmHg
• PKA: 4.75±0.10(Predicted)
• Flash Point: 288.4°C
• PSA: 94.83000
• Density: 1.148g/cm³
• 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:

98%Min ^*data from raw suppliers

8-iso Prostaglandin E2 ≥99% ^*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: 8-?iso Prostaglandin E2 is a Prostaglandin formed from arachidonic acid. 8-?iso Prostaglandin E2 is an inhibitor of endogenous amino acid neurotransmitter levels in bovine retina.

Technology Process of 8-isoprostaglandin E2

There total 30 articles about 8-isoprostaglandin 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: 92.0%

15-E2t-isoprostane methyl ester (31753-18-1) → 8-isoprostaglandin E2 (27415-25-4)

Guidance literature:

With water; In tert-butyl methyl ether; at 35 ℃; for 18h; Enzymatic reaction;

DOI:10.1021/jo101806m

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:

Methyl (Z)-7-<(3R)-3-Hydroxy-5-oxo-1-cyclopentenyl>-5-heptenoate (42541-96-8) → 8-isoprostaglandin E2 (27415-25-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: imidazole; Et₃N / dimethylformamide

2.1: n-BuLi; MeLi; CuCN / diethyl ether / -78 °C

2.2: 54 percent / methyl acetoacetate / diethyl ether / -78 °C

3.1: 78 percent / HF; Py / tetrahydrofuran / 20 °C

4.1: 50 percent / porcine pancreatic lipase; NaCl; CaCl₂ / H₂O; tetrahydrofuran / 20 °C

With pyridine; 1H-imidazole; n-butyllithium; porcine pancreatic lipase; hydrogen fluoride; methyllithium; triethylamine; sodium chloride; calcium chloride; In tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(02)02252-9

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