5-trans-PGF2alpha

Base Information

• Chemical Name: 5-trans-PGF2alpha
• CAS No.: 551-11-1
• Molecular Formula: C20H34O5
• Molecular Weight: 354.487
• UNII: EM5T9R5FAS
• DSSTox Substance ID: DTXSID501317801
• Nikkaji Number: J1.068.163D
• Wikidata: Q63398817
• Metabolomics Workbench ID: 2438
• Mol file: 551-11-1.mol

Synonyms:9alpha,11beta PGF2;9alpha,11beta-PGF2;alpha, PGF2;Dinoprost;Enzaprost F;Estrofan;F2 alpha, Prostaglandin;F2alpha, Prostaglandin;PGF2;PGF2 alpha;PGF2alpha;Prostaglandin F2;Prostaglandin F2 alpha;Prostaglandin F2alpha

Chemical Property of 5-trans-PGF2alpha

Chemical Property:

• Appearance/Colour: White to off-white crystalline solid
• Vapor Pressure: 1.71E-13mmHg at 25°C
• Melting Point: 25-35°
• Refractive Index: 1.569
• Boiling Point: 531 °C at 760 mmHg
• PKA: pKa 4.90(H2O,t=25±2,I=0.0，c<0.01,N2) (Uncertain)
• 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

Prostaglandin F2α ^*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
• Description: Prostaglandin F2α (PGF2α) is a widely distributed PG occurring in many species. It causes contraction of vascular, bronchial, intestinal, and myometrial smooth muscle, and also exhibits potent luteolytic activity. PGF2α exerts its receptor mediated physiological activity at 50-100 nM. Maximal ovine myometrial contraction can be achieved at 125 nM PGF2α in vitro.
• Uses: Prostaglandin F2α is one of the most biologically studied of the primary prostaglandins. Closely related to Prostaglandin E2 (PGE2) in that both prostaglandins are biosynthesized from the same precursors and that PGF2 is the synthetic reduction product of PGE2.

Technology Process of 5-trans-PGF2alpha

There total 257 articles about 5-trans-PGF2alpha 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: 99.0%

(Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((S,E)-3-(tert-butyldimethylsilyloxy)oct-1-enyl)-5-(triethylsilyloxy)cyclopentyl)hept-5-enoic acid → dinoprost (551-11-1)

Guidance literature:

With hydrogenchloride; In water; acetone; at 20 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1016/j.tet.2019.130593

Reference yield: 95.0%

methyl (5Z)-7-{(1R,2R,3R,5R)-5-acetoxy-3-hydroxy-2-[(1E,3S)-3-hydroxy-1-octenyl]cyclopentyl}-5-heptenoate (55022-57-6) → dinoprost (551-11-1)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; Ambient temperature;

DOI:10.1055/s-1997-3268

Reference yield: 90.0%

(Z)-7-((1R,2R,3R,5S)-3-[(tert-butyldimethylsilanyl)oxy]-2-{(S,E)-3-[(tert-butyldimethylsilanyl)oxy]oct-1-en-1-yl}-5-hydroxycyclopentyl)hept-5-enoic acid (1239683-12-5) → dinoprost (551-11-1)

Guidance literature:

With hydrogen fluoride; water; In acetonitrile; at 20 ℃; for 7h; stereoselective reaction;

DOI:10.1016/j.tet.2010.07.069

upstream raw materials:

(+)-prostaglandin F_2α

dinoprostone

(3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol

5-(Triphenyl-λ⁵-phosphanylidene)-pentanoic acid anion

Downstream raw materials:

(Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid 2-(2,5-dimethoxy-phenyl)-2-oxo-ethyl ester

(+)-prostaglandin F_2α

Dihydro-PGF1alpha

dinoprost tromethamine

Refernces

A MILD METHOD FOR THE SYNTHESIS OF 2-KETOPYRROLES FROM CARBOXYLIC ACIDS

10.1016/S0040-4039(01)83003-3

The study presents a mild and efficient method for synthesizing 2-ketopyrroles from carboxylic acids. The key chemicals involved in this synthesis are 2-pyridylthiolesters and pyrrylmagnesium chloride. The process begins with the conversion of a carboxylic acid to a 2-pyridylthiolester using 2,2'-dipyridyl-disulfide and triphenylphosphine in toluene at 25°C under an argon atmosphere. Subsequently, pyrrylmagnesium chloride is added at -78°C, leading to the formation of the 2-ketopyrrole product. This method is notable for its mildness, selectivity, and efficiency, making it suitable for the synthesis of complex polyfunctional molecules. The study demonstrates the versatility of this method by synthesizing various 2-ketopyrroles, including those derived from biologically active molecules such as pinanethromboxane A2, prostaglandin F2a, and monensin. The synthesized 2-ketopyrroles are isolated in excellent yields using techniques like preparative layer chromatography or flash column chromatography.