Prostaglandin F2beta

Base Information

• Chemical Name: Prostaglandin F2beta
• CAS No.: 4510-16-1
• Molecular Formula: C20H34O5
• Molecular Weight: 354.487
• ChEMBL ID: CHEMBL1894513
• DSSTox Substance ID: DTXSID40859478
• Metabolomics Workbench ID: 2392
• Nikkaji Number: J20.420J
• Wikidata: Q27103967
• Mol file: 4510-16-1.mol

Synonyms:PGF2beta;prostaglandin F2beta;prostaglandin F2beta, (5Z,8beta,9beta,11alpha,12alpha,13E,15S)-isomer;prostaglandin F2beta, (5Z,9beta,11beta,13E,15R)-isomer;prostaglandin F2beta, (5Z,9beta,11beta,13E,15S)-isomer

Chemical Property of Prostaglandin F2beta

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 1.71E-13mmHg at 25°C
• Melting Point: 105-106°C
• Refractive Index: 1.569
• Boiling Point: 531 °C at 760 mmHg
• Flash Point: 289 °C
• PSA: 97.99000
• Density: 1.153 g/cm³
• LogP: 3.04290
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 354.24062418
• Heavy Atom Count: 25
• Complexity: 432

Purity/Quality:

99% ^*data from raw suppliers

9β,11α-ProstaglandinF2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC(C=CC1C(CC(C1CC=CCCCC(=O)O)O)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@H]([C@@H]1C/C=C\CCCC(=O)O)O)O)O
• Uses: 9beta,11alpha-Prostaglandin F2 is the C-9 epimer of PGF2α, a bronchodilator that exhibits negative chronotopic activity.

Technology Process of Prostaglandin F2beta

There total 76 articles about Prostaglandin F2beta 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: 57.0%

C15H26O4 + (4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → prostaglandin F2α (551-11-1,4510-16-1,13164-29-9,23518-25-4,23518-26-5,27415-26-5,28977-22-2,36150-01-3,36150-02-4,37658-84-7,38310-95-1,38432-87-0,39762-37-3,42586-88-9,51262-67-0,51830-20-7,51830-21-8,52521-76-3,54324-23-1,54324-24-2,54324-25-3,54483-31-7,54483-32-8,57759-78-1,57759-79-2,57759-85-0,58717-39-8,59727-54-7,61046-31-9,61302-52-1,62446-65-5,64395-46-6,65026-00-8,65026-01-9,88391-39-3,88391-40-6,99880-86-1,117558-80-2,118456-51-2,123123-44-4,125411-82-7,146388-90-1)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1038/nature11411

Reference yield:

dinoprostone (363-24-6) → dinoprost (551-11-1) + Prostaglandin F2b (4510-16-1)

Guidance literature:

With ammonia; lithium; In tetrahydrofuran; Product distribution;

Reference yield:

(3aR,6aS)-2-methoxy-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-5-carbaldehyde → prostaglandin F2α (551-11-1,4510-16-1,13164-29-9,23518-25-4,23518-26-5,27415-26-5,28977-22-2,36150-01-3,36150-02-4,37658-84-7,38310-95-1,38432-87-0,39762-37-3,42586-88-9,51262-67-0,51830-20-7,51830-21-8,52521-76-3,54324-23-1,54324-24-2,54324-25-3,54483-31-7,54483-32-8,57759-78-1,57759-79-2,57759-85-0,58717-39-8,59727-54-7,61046-31-9,61302-52-1,62446-65-5,64395-46-6,65026-00-8,65026-01-9,88391-39-3,88391-40-6,99880-86-1,117558-80-2,118456-51-2,123123-44-4,125411-82-7,146388-90-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / tetrahydrofuran

2.1: ozone / methanol; dichloromethane / -78 °C

2.2: -78 - 20 °C

3.1: hydrogenchloride / tetrahydrofuran; water / 16 h / 20 °C

4.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C

With hydrogenchloride; potassium tert-butylate; ozone; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1038/nature11411

upstream raw materials:

dinoprostone

9,11-Dibenzyl-PGF_2β

Biphenyl-4-carboxylic acid 2-{(1R,2R,3R,5R)-3,5-bis-benzyloxy-2-[(E)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethyl ester

2-{(1R,2R,3R,5R)-3,5-Bis-benzyloxy-2-[(E)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-ethanol

Refernces

• 1、 Mahrwald, Rainer,Schick, Hans,Pivnitsky, Kasimir K.,Schwarz, Sigfrid. "Prostaglandins and Prostaglandin Intermediates. Part 26 A Novel Route to PGF2α using Triisopropoxy-hept-1-ynyl-titanium as Precursor for the β-Side Chain". . p. 403 - 413. Retrieved 2007/10/02.
• 2、 Marino, Joseph P.,Pradilla, Roberto F. de la,Laborde, Edgardo. "Regio- and Stereoselectivity of the Reaction between Cyanocuprates and Cyclopentene Epoxides. Application to the Total Synthesis of Prostaglandins". . p. 4898 - 4913. Retrieved 2007/10/02.