6-Keto-prostaglandin F1alpha

Base Information

• Chemical Name: 6-Keto-prostaglandin F1alpha
• CAS No.: 58962-34-8
• Molecular Formula: C20H34O6
• Molecular Weight: 370.486
• Hs Code.: 2937909000
• European Community (EC) Number: 682-018-4
• UNII: 8URB805JJJ
• ChEMBL ID: CHEMBL2074840
• DSSTox Substance ID: DTXSID001317937
• Metabolomics Workbench ID: 2371
• NCI Thesaurus Code: C152068
• Nikkaji Number: J240.195I
• Wikidata: Q27103534
• Mol file: 58962-34-8.mol

Synonyms:6 Keto PGF1 alpha;6 Ketoprostaglandin F1 alpha;6 Oxo PGF1 alpha;6 Oxoprostaglandin F1 alpha;6-Keto-PGF1 alpha;6-Ketoprostaglandin F1 alpha;6-Oxo-PGF1 alpha;6-Oxoprostaglandin F1 alpha;alpha, 6-Keto-PGF1;alpha, 6-Ketoprostaglandin F1;alpha, 6-Oxo-PGF1;alpha, 6-Oxoprostaglandin F1;F1 alpha, 6-Ketoprostaglandin;F1 alpha, 6-Oxoprostaglandin

Chemical Property of 6-Keto-prostaglandin F1alpha

Chemical Property:

• Vapor Pressure: 1.25E-15mmHg at 25°C
• Refractive Index: 1.561
• Boiling Point: 575.3 °C at 760 mmHg
• PKA: 4.69±0.10(Predicted)
• Flash Point: 315.8 °C
• PSA: 115.06000
• Density: 1.191 g/cm³
• LogP: 2.44590
• Storage Temp.: −20°C
• Solubility.: ethanol: 10 mg/mL, clear, faintly yellow
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 370.23553880
• Heavy Atom Count: 26
• Complexity: 461

Purity/Quality:

99% ^*data from raw suppliers

Prostaglandin F1 alpha, 6-keto ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC(C=CC1C(CC(C1CC(=O)CCCCC(=O)O)O)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1CC(=O)CCCCC(=O)O)O)O)O
• Description: 6-keto prostaglandin F1α (6-keto PGF1α) is the inactive, non-enzymatic hydrolysis product of PGI2. 6-keto PGF1α serves as a useful marker of PGI2 biosynthesis in vivo. When [3H]-PGI2 is injected into healthy human males, 6.6% of the radioactivity is recovered from urine as [3H]-6-keto PGF1α.
• Uses: 6-Ketoprostaglandin F1α is the stable hydrolysis product of prostacyclin (P839060), an eicosanoid which prevents the formation of platelet plugs and an effective vasodilator.

Technology Process of 6-Keto-prostaglandin F1alpha

There total 18 articles about 6-Keto-prostaglandin F1alpha 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: 84.0%

6-keto-PGF1α methyl ester (63557-55-1) → 7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-6-oxo-heptanoic acid (58962-34-8)

Guidance literature:

With sodium hydroxide; In methanol; at 40 ℃; for 3h;

DOI:10.1016/S0040-4039(01)91266-3

Reference yield:

prostacyclin*α-cyclodextrin (77192-49-5) → 7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-6-oxo-heptanoic acid (58962-34-8) + alpha cyclodextrin (10016-20-3)

Guidance literature:

With phosphate buffer (pH=ca. 7); water; at 10 - 30 ℃; Thermodynamic data; Kinetics; activation parameters: ΔS(excit.), ΔG(excit.), E investigated;

DOI:10.1248/cpb.29.213

Reference yield:

prostacyclin*β-cyclodextrin (77164-53-5) → 7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-6-oxo-heptanoic acid (58962-34-8) + β‐cyclodextrin (7585-39-9)

Guidance literature:

With phosphate buffer (pH=ca. 7); water; at 10 - 30 ℃; Thermodynamic data; Kinetics; activation parameters: ΔS(excit.), ΔG(excit.), E investigated;

DOI:10.1248/cpb.29.213

upstream raw materials:

Epoprostenol

6-keto-PGF_1α methyl ester

prostacyclin*α-cyclodextrin

prostacyclin*β-cyclodextrin

Downstream raw materials:

6-keto-PGF_1α methyl ester

Refernces

• 1、 Chiang,Cho,Euser,Kresge. "Prostacyclin: Evidence that intramolecular general-acid catalysis by its carboxylic acid group is responsible for the extra hydrolytic lability". . p. 4192 - 4196. Retrieved 2007/10/02.
• 2、 Uekama,Hirayama,Wakuda,Otagiri. "Effects of cyclodextrins on the hydrolysis of prostacyclin and its methyl ester in aqueous solution". . p. 213 - 219. Retrieved 2007/10/02.