15-keto-PGF1alpha

Base Information

• Chemical Name: 15-keto-PGF1alpha
• CAS No.: 21562-58-3
• Molecular Formula: C20H34O5
• Molecular Weight: 354.487
• DSSTox Substance ID: DTXSID20332375
• Nikkaji Number: J428.386D
• Wikidata: Q27140001
• Metabolomics Workbench ID: 2492
• Mol file: 21562-58-3.mol

Synonyms:15-keto-PGF1alpha;15-ketoprostaglandin F1alpha;15-oxo-PGF1alpha;15k-PGF1a;9S,11R-dihydroxy-15-oxo-13E-prostaenoic acid;15-oxoprostaglandin F1alpha;15-keto-Prostaglandin F1alpha;(9alpha,11alpha,13E)-9,11-dihydroxy-15-oxoprost-13-en-1-oic acid;9alpha,11alpha-Dihydroxy-15-oxo-prost-13E-en-1-oic acid;7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E)-3-oxooct-1-enyl]cyclopentyl]heptanoic acid;7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((E)-3-oxooct-1-enyl)cyclopentyl)heptanoic acid;15-KetoPGF1alpha;LMFA03010150;15-keto Prostaglandin F1??;CHEBI:72593;DTXSID20332375;HMS3648N03;AKOS040756159;PD021105;SR-01000946453;J-014148;SR-01000946453-1;Q27140001

Chemical Property of 15-keto-PGF1alpha

Chemical Property:

• PSA: 94.83000
• LogP: 3.47510
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 13
• Exact Mass: 354.24062418
• Heavy Atom Count: 25
• Complexity: 432

Purity/Quality:

98% ^*data from raw suppliers

15-keto Prostaglandin F1α ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(=O)C=CC1C(CC(C1CCCCCCC(=O)O)O)O
• Isomeric SMILES: CCCCCC(=O)/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1CCCCCCC(=O)O)O)O
• Description: 15-keto PGF1α is the initial metabolite of PGF1α via 15-hydroxy PGDH. In mammals, oxidation of C-15 markedly attenuates receptor binding and activity. In fish, the 15-keto compounds serve as post-ovulatory pheromones and are more active than the parent prostaglandins.

Technology Process of 15-keto-PGF1alpha

There total 2 articles about 15-keto-PGF1alpha 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:

C22H38O6 → ALPROSTADIL (745-65-3) + (9α,11α,13E)-9,11-dihydroxy-15-oxoprost-13-en-1-oic acid (21562-58-3)

Guidance literature:

C₂₂H₃₈O₆; With 3,4-dihydro-2H-pyran; pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 27h;

With potassium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 12h; Further stages;

DOI:10.1134/S1070428014010266

Reference yield:

( 13E )-9α-acetoxy-11α-hydroxy-15-oxoprost-13-enoic acid methyl ester → ALPROSTADIL (745-65-3) + (9α,11α,13E)-9,11-dihydroxy-15-oxoprost-13-en-1-oic acid (21562-58-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: diisobutylaluminium 2,6-di-tert-butyl-4-methylphenoxide / -78 °C

2.1: pyridinium p-toluenesulfonate; 3,4-dihydro-2H-pyran / dichloromethane / 27 h / 20 °C

2.2: 12 h / 20 °C

With 3,4-dihydro-2H-pyran; diisobutylaluminium 2,6-di-tert-butyl-4-methylphenoxide; pyridinium p-toluenesulfonate; In dichloromethane;

DOI:10.1134/S1070428014010266

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