15-Keto-PGF2alpha

Base Information

• Chemical Name: 15-Keto-PGF2alpha
• CAS No.: 35850-13-6
• Molecular Formula: C20H32O5
• Molecular Weight: 352.471
• DSSTox Substance ID: DTXSID801317581
• Metabolomics Workbench ID: 2393
• Nikkaji Number: J366.794D
• Wikidata: Q27103699
• Mol file: 35850-13-6.mol

Synonyms:15-keto-PGF2alpha;15-keto-prostaglandin F2 alpha;15-ketoprostaglandin F2alpha

Chemical Property of 15-Keto-PGF2alpha

Chemical Property:

• Vapor Pressure: 1.1E-13mmHg at 25°C
• Refractive Index: 1.561
• Boiling Point: 535.2 °C at 760 mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 291.5 °C
• PSA: 94.83000
• Density: 1.149 g/cm³
• LogP: 3.25110
• Storage Temp.: −20°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 352.22497412
• Heavy Atom Count: 25
• Complexity: 469

Purity/Quality:

98%Min ^*data from raw suppliers

15-keto Prostaglandin F2α ≥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(C1CC=CCCCC(=O)O)O)O
• Isomeric SMILES: CCCCCC(=O)/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O
• Description: 15-keto Prostaglandin F2α (15-keto PGF2α) is the first metabolite of PGF2α (Item Nos. 16010 | 10007221). in the 15-hydroxy PGDH pathway. It is one of the critical components in the goldfish and Atlantic salmon postovulatory pheromone. 15-keto PGF2α stimulates the male goldfish and salmon olfactory receptors with detection thresholds of 10-12 and 10-8 M, respectively. 15-keto PGF2α is 10-fold less active than PGF2α in decreasing rabbit intraocular pressure.15-keto PGF2α MaxSpec? standard is a quantitative grade standard of 15-keto PGF2α that has been prepared specifically for mass spectrometry or any application where quantitativereproducibility is required. The solution has been prepared gravimetrically and is supplied in a deactivated glass ampule sealed under argon. The concentration was verified by comparison to an independentlyprepared calibration standard. This 15-keto PGF2α MaxSpec? standard is guaranteed to meet identity, purity, stability, and concentration specifications and is provided with a batch-specific certificate of analysis.Ongoing stability testing is performed to ensure the concentration remains accurate throughout the shelf life of the product. Note: The amount of solution added to the vial is in excess of the listed amount. Therefore, itis necessary to accurately measure volumes for preparation of calibration standards. Follow recommended storage and handling conditions to maintain product quality.
• Uses: 15-keto Prostaglandin F2α (15-keto PGF2α) is the first metabolite of PGF2α. in the 15-hydroxy PGDH pathway. It is one of the critical components in the goldfish and Atlantic salmon postovulatory pheromone. 15-keto PGF2α stimulates the male goldfish and salmon olfactory receptors with detection thresholds of 10-12 and 10-8 M, respectively. 15-keto PGF2α is 10-fold less active than PGF2α in decreasing rabbit intraocular pressure.

Technology Process of 15-Keto-PGF2alpha

There total 18 articles about 15-Keto-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: 20.0%

prostaglandin G2 → dinoprost (551-11-1) + 15-Keto PGF2a (35850-13-6) + 15-OOH-PGF2α

Guidance literature:

In water; for 0.166667h; Gersemia fruticosa preparation, pH 8.5;

DOI:10.1016/0040-4039(94)88299-1

Reference yield:

C15H24O4 + (4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → 15-Keto PGF2a (35850-13-6)

Guidance literature:

(4-carboxybutyl)triphenylphosphonium bromide; With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hexamethyldisilazane; In tetrahydrofuran; at -40 - -25 ℃; for 1.5h;

C₁₅H₂₄O₄; In tetrahydrofuran; at 20 ℃;

Reference yield:

(-)-7α-Hydroxy-3-oxo-6β-<3-oxo-1(E)-octenyl>-cis-2-oxabicyclo<3.3.0>octane (60623-67-8) → 15-Keto PGF2a (35850-13-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); zinc(II) tetrahydroborate / 1,2-dimethoxyethane / 24 h / -15 - -10 °C

1.2: 1 h / 0 - 20 °C

2.1: C₁₀H₁₆NO^(1-); potassium bromide; tetrabutylammomium bromide / dichloromethane / 0.17 h / 0 °C

2.2: 0.5 h / 5 °C

3.1: N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hexamethyldisilazane / tetrahydrofuran / 1.5 h / -40 - -25 °C

3.2: 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; zinc(II) tetrahydroborate; C₁₀H₁₆NO^(1-); tetrabutylammomium bromide; sodium hexamethyldisilazane; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); potassium bromide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;

upstream raw materials:

15-keto-PGG₂

(-)-7α-Hydroxy-3-oxo-6β-<3-oxo-1(E)-octenyl>-cis-2-oxabicyclo<3.3.0>octane

(4-carboxybutyl)triphenylphosphonium bromide

prostaglandin D₂

Refernces

• 1、 -. "A simple and efficient synthesis of the front row element of the method". . . Retrieved 2018/12/02.
• 2、 Baraldi, P. G.,Barco, A.,Benetti, S.,Pollini, G. P.,Simoni, D.,Zanirato, V.. "STEREOSPECIFIC NITROMETHANE CONJUGATE ADDITION TO 4-OXYGENATED-2-SUBSTITUTED-CYCLOPENT-2-ENONES: A SIMPLE APPROACH TO PROSTAGLANDINS". . p. 4669 - 4678. Retrieved 2007/10/02.