Prostaglandin D3

Base Information

• Chemical Name: Prostaglandin D3
• CAS No.: 71902-47-1
• Molecular Formula: C₂₀H₃₀O₅
• Molecular Weight: 350.455
• UNII: 895XE61E0I
• Metabolomics Workbench ID: 2484
• Nikkaji Number: J39.537D
• Wikidata: Q28529673
• Mol file: 71902-47-1.mol

Synonyms:PGD3;prostaglandin D3

Chemical Property of Prostaglandin D3

Chemical Property:

• Vapor Pressure: 6.25E-15mmHg at 25°C
• Boiling Point: 561.2 °C at 760 mmHg
• Flash Point: 307.2 °C
• PSA: 94.83000
• Density: 1.166 g/cm³
• LogP: 3.02710
• XLogP3: 2
• 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:

99% ^*data from raw suppliers

9alpha,15S-Dihydroxy-11-oxo-prosta-5Z,13E,17Z-trien-1-oicacid 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC(C=CC1C(C(CC1=O)O)CC=CCCCC(=O)O)O
• Isomeric SMILES: CC/C=C\C[C@@H](/C=C/[C@@H]1[C@H]([C@H](CC1=O)O)C/C=C\CCCC(=O)O)O
• Uses: Prostaglandin D3 (PGD3) is produced by the metabolism of EPA via the COX pathway. It is equipotent to PGD2 in decreasing systemic blood pressure in rats and in decreasing intraocular pressure in rabbits. However, it is 3-5 times more potent than PGD2 in the inhibition of ADP-induced human platelet aggregation.[Cayman Chemical]

Technology Process of Prostaglandin D3

There total 13 articles about Prostaglandin D3 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: 68.0%

(E)-7-{(1R,2R,5S)-3-Oxo-5-(tetrahydro-pyran-2-yloxy)-2-[(1E,5E)-(S)-3-(tetrahydro-pyran-2-yloxy)-octa-1,5-dienyl]-cyclopentyl}-hept-5-enoic acid methyl ester → (E)-7-[(1R,2R,5S)-5-Hydroxy-2-((1E,5E)-(S)-3-hydroxy-octa-1,5-dienyl)-3-oxo-cyclopentyl]-hept-5-enoic acid (71902-47-1)

Guidance literature:

With acetic acid; In water;

DOI:10.1246/cl.1980.377

Reference yield:

(3aR,4R,5R,6aS)-4-((1E,5E)-(S)-3-Hydroxy-octa-1,5-dienyl)-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one (32233-42-4) → (E)-7-[(1R,2R,5S)-5-Hydroxy-2-((1E,5E)-(S)-3-hydroxy-octa-1,5-dienyl)-3-oxo-cyclopentyl]-hept-5-enoic acid (71902-47-1)

Guidance literature:

Multi-step reaction with 11 steps

2: diisobutylaluminium hydride / toluene / -78 °C

4: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

5: 57 percent / p-toluenesulphonic acid / methanol / Ambient temperature

6: pyridine / CH₂Cl₂

7: 93 percent / K₂CO₃ / methanol / 0.17 h / 0 °C

8: p-toluenesulfonic acid / CH₂Cl₂

9: 85 percent / KOH / H₂O; ethanol / 2 h / 45 °C

10: 85 percent / chromic acid

11: 68 percent / acetic acid / H₂O

With pyridine; potassium hydroxide; chromic acid; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; In methanol; ethanol; dichloromethane; water; toluene;

DOI:10.1246/cl.1980.377

Reference yield:

(3aR,4R,5R,6aS)-4-[(1E,5E)-(S)-3-(1-Methoxy-1-methyl-ethoxy)-octa-1,5-dienyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol (75351-53-0) → (E)-7-[(1R,2R,5S)-5-Hydroxy-2-((1E,5E)-(S)-3-hydroxy-octa-1,5-dienyl)-3-oxo-cyclopentyl]-hept-5-enoic acid (71902-47-1)

Guidance literature:

Multi-step reaction with 9 steps

2: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

3: 57 percent / p-toluenesulphonic acid / methanol / Ambient temperature

4: pyridine / CH₂Cl₂

5: 93 percent / K₂CO₃ / methanol / 0.17 h / 0 °C

6: p-toluenesulfonic acid / CH₂Cl₂

7: 85 percent / KOH / H₂O; ethanol / 2 h / 45 °C

8: 85 percent / chromic acid

9: 68 percent / acetic acid / H₂O

With pyridine; potassium hydroxide; chromic acid; potassium carbonate; toluene-4-sulfonic acid; acetic acid; In methanol; ethanol; dichloromethane; water;

DOI:10.1246/cl.1980.377

upstream raw materials:

(3aR,4R,5R,6aS)-4-((1E,5E)-(S)-3-Hydroxy-octa-1,5-dienyl)-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one

(3aR,4R,5R,6aS)-4-[(1E,5E)-(S)-3-(1-Methoxy-1-methyl-ethoxy)-octa-1,5-dienyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol

(3aR,4R,5R,6aS)-4-[(1E,5E)-(S)-3-(1-Methoxy-1-methyl-ethoxy)-octa-1,5-dienyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one

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

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