PROSTAGLANDIN J2

Base Information

• Chemical Name: PROSTAGLANDIN J2
• CAS No.: 60203-57-8
• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.456
• Mol file: 60203-57-8.mol

Synonyms:9,10-Didehydro-9-deoxy-PGD2;PGJ2; Prostaglandin J2

Chemical Property of PROSTAGLANDIN J2

Chemical Property:

• Vapor Pressure: 4.57E-13mmHg at 25°C
• Boiling Point: 521.7°C at 760 mmHg
• PKA: 4.75±0.10(Predicted)
• Flash Point: 283.4°C
• PSA: 74.60000
• Density: 1.103g/cm³
• LogP: 4.05630
• Storage Temp.: −20°C

Purity/Quality:

≥95% ^*data from raw suppliers

PGJ2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi,F
• Statements: 20/21/22-36/37/38-67-66-36-11
• Safety Statements: 26-36-33-29-16

MSDS Files:

SDS file from LookChem

Useful:

• Description: Prostaglandin J2 (PGJ2) is formed from PGD2 by the elimination of the C-9 hydroxyl group, a process which is accelerated by the presence of albumin. PGJ2 inhibits platelet aggregation with an IC50 of about 5-10 nM. PGJ2 has antimitotic and antiproliferative effects on a variety of cultured normal cells and tumor cell lines. However, this activity has been attributed to further metabolites of PGJ2 and not the parent compound itself.
• Uses: PGJ2 (Prostaglandin J2) is a Prostaglandin D2 metabolite that has shown potent anti-neoplastic and antiviral activity.

Technology Process of PROSTAGLANDIN J2

There total 33 articles about PROSTAGLANDIN J2 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: 88.0%

(5Z)-7-{(1S,5R)-5-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-4-oxo-cyclopent-2-enyl}-hept-5-enoic acid (587869-89-4) → prostaglandin J2 (60203-57-8)

Guidance literature:

With hydrogen fluoride; In acetonitrile; at -20 ℃; for 4h;

DOI:10.1021/jo034502h

Reference yield: 25.0%

(Z)-7-{(1R,5S)-5-[(E)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-4-oxo-cyclopent-2-enyl}-hept-5-enoic acid → (+/-)-prostaglandin-J2 (60203-57-8,72974-57-3,73712-08-0,74364-97-9,76820-67-2) + (Z)-7-[(1R,5S)-5-((E)-(S)-3-Hydroxy-oct-1-enyl)-4-oxo-cyclopent-2-enyl]-hept-5-enoic acid (60203-57-8,72974-57-3,73712-08-0,74364-97-9,76820-67-2)

Guidance literature:

With hydrogen fluoride; In acetonitrile; for 1h;

DOI:10.1055/s-2003-39885

Reference yield: 25.0%

(Z)-7-{(1R,5S)-5-[(E)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-4-oxo-cyclopent-2-enyl}-hept-5-enoic acid → (+/-)-prostaglandin-J2 (60203-57-8,72974-57-3,73712-08-0,74364-97-9,76820-67-2) + (Z)-7-[(1R,5S)-5-((E)-(S)-3-Hydroxy-oct-1-enyl)-4-oxo-cyclopent-2-enyl]-hept-5-enoic acid (60203-57-8,72974-57-3,73712-08-0,74364-97-9,76820-67-2)

Guidance literature:

With hydrogen fluoride; In acetonitrile; for 1h;

DOI:10.1055/s-2003-39885

upstream raw materials:

9-deoxy-9,10-dehydro-15-t-butyldimethylsilyloxyprostaglandin D₂

(4-carboxybutyl)triphenylphosphonium bromide

<5-<3'-(dimethyl-t-butylsilyloxy)oct-1'-enyl>-4-hydroxycyclopent-2-enyl>acetaldehyde

4-exo-(3'-t-butyldimethylsilyloxyoct-1'-enyl)-6-endo-hydroxymethylbicyclo<3.1.0>hex-2-ene

Downstream raw materials:

15-deoxy-delta prostaglandin J₂

Δ12-prostaglandin J2

Refernces

• 1、 Zanoni, Giuseppe,Porta, Alessio,de Toma, Quintino,Castronovo, Francesca,Vidari, Giovanni. "First enantioselective total synthesis of (8S,12R,15S)-prostaglandin J2". . p. 6437 - 6439. Retrieved 2007/10/03.