prostaglandin G2

Base Information

• Chemical Name: prostaglandin G2
• CAS No.: 51982-36-6
• Molecular Formula: C20H32 O6
• Molecular Weight: 368.47
• UNII: AZ87DUD2Y8
• DSSTox Substance ID: DTXSID00866229
• Metabolomics Workbench ID: 2379
• Nikkaji Number: J10.404C
• Wikidata: Q19835971
• Wikipedia: Prostaglandin_G2
• Mol file: 51982-36-6.mol

Synonyms:PGG(2);PGG2;prostaglandin G2

Chemical Property of prostaglandin G2

Chemical Property:

• Appearance/Colour: acetone solution
• Vapor Pressure: 7.3E-13mmHg at 25°C
• Boiling Point: 517.3 °C at 760 mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 175.5 °C
• PSA: 85.22000
• Density: 1.157 g/cm³
• LogP: 4.51740
• Storage Temp.: −70°C
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 368.21988874
• Heavy Atom Count: 26
• Complexity: 475

Purity/Quality:

99% ^*data from raw suppliers

Prostaglandin G2 ≥95% (HPLC), acetone solution ^*data from reagent suppliers

Safty Information:

• Pictogram(s): FXi
• Hazard Codes: F,Xi
• Statements: 11-36-66-67
• Safety Statements: 9-16-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC(C=CC1C2CC(C1CC=CCCCC(=O)O)OO2)OO
• Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@H]2C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)OO2)OO
• Uses: Prostaglandin G2 is the first intermediary in the COX pathway which is stable enough to be isolated and characterized. It maintains the ability to inhibit indoleamine 2,3-dioxygenase activity and affect immune suppression and tumor induce tolerance.

Technology Process of prostaglandin G2

There total 7 articles about prostaglandin G2 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:

(Z)-7-[(1S,2S,3R,5S)-3,5-Dibromo-2-((E)-(S)-3-chloro-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid (73991-36-3) → PGG2 (51982-36-6)

Guidance literature:

With dihydrogen peroxide; silver trifluoroacetate; In diethyl ether; Yield given;

DOI:10.1021/ja00523a056

Reference yield:

(Z)-7-[(1S,2S,3R,5S)-3,5-Dibromo-2-((E)-(S)-3-chloro-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid methyl ester (73991-35-2) → PGG2 (51982-36-6)

Guidance literature:

Multi-step reaction with 2 steps

1: commercial hog pancrease lipase

2: silver trifluoroacetate, 90percent H₂O₂ / diethyl ether

With commercial hog pancrease lipase; dihydrogen peroxide; silver trifluoroacetate; In diethyl ether;

DOI:10.1021/ja00523a056

Reference yield:

(Z)-7-[(1S,2S,3R,5S)-3,5-Dibromo-2-((E)-(R)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid methyl ester (65147-40-2,65147-41-3,65185-29-7) → PGG2 (51982-36-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / 2-chloro-3-ethylbenzoxazolium tetrafluoroborate, benzyltributylammonium chloride / CH₂Cl₂ / 0.5 h / Ambient temperature

2: commercial hog pancrease lipase

3: silver trifluoroacetate, 90percent H₂O₂ / diethyl ether

With 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate; commercial hog pancrease lipase; dihydrogen peroxide; silver trifluoroacetate; benzyltri(n-butyl)ammonium chloride; In diethyl ether; dichloromethane;

DOI:10.1021/ja00523a056

upstream raw materials:

(Z)-7-[(1S,2S,3R,5S)-3,5-Dibromo-2-((E)-(S)-3-chloro-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid

all cis 5,8,11,14-eicosatetraenoic acid

(Z)-7-[(1S,2S,3R,5S)-3,5-Dibromo-2-((E)-(S)-3-chloro-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid methyl ester

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

Downstream raw materials:

prostaglandin H₂

5-trans-PGF_2α

dinoprost