prostaglandin B2

Base Information

• Chemical Name: prostaglandin B2
• CAS No.: 13367-85-6
• Molecular Formula: C20H30 O4
• Molecular Weight: 334.456
• European Community (EC) Number: 635-050-8
• UNII: BIU61O9T9T
• ChEMBL ID: CHEMBL1901620
• DSSTox Substance ID: DTXSID50864391
• Metabolomics Workbench ID: 2385
• Nikkaji Number: J16.062H
• Wikidata: Q27093323
• Mol file: 13367-85-6.mol

Synonyms:PGB2;prostaglandin B2

Chemical Property of prostaglandin B2

Chemical Property:

• Vapor Pressure: 8.99E-14mmHg at 25°C
• Boiling Point: 537°Cat760mmHg
• PKA: 4.74±0.10(Predicted)
• Flash Point: 292.6°C
• PSA: 74.60000
• Density: 1.118g/cm³
• LogP: 4.34450
• Storage Temp.: −20°C
• Solubility.: ethanol: ~100 mg/mL
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 12
• Exact Mass: 334.21440943
• Heavy Atom Count: 24
• Complexity: 500

Purity/Quality:

95-99% ^*data from raw suppliers

PGB2(ProstaglandinB2) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi,F
• Hazard Codes: Xn,Xi,F
• Statements: 20/21/22-67-66-36-11
• Safety Statements: 36/37-26-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC(C=CC1=C(C(=O)CC1)CC=CCCCC(=O)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/C1=C(C(=O)CC1)C/C=C\CCCC(=O)O)O
• Description: Prostaglandin B2 (PGB2) is a non-enzymatic dehydration product resulting from the treatment of PGE2 or PGA2 (Item Nos. 10210 | 10007199) with strong base. It has weak agonist activity on TP receptors and can increase pulmonary blood pressure in the rabbit at relatively high doses (5 μg/kg).PGB2 MaxSpec? standard is a quantitative grade standard of PGB2 that has been prepared specifically for mass spectrometry or any application where quantitative reproducibility 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 independently prepared calibration standard. This PGB2 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, it is necessary to accurately measure volumes for preparation of calibration standards. Follow recommended storage and handling conditions to maintain product quality.
• Uses: PGB2 (Prostaglandin B2) is an abundant prostaglandin released from osteoblasts.

Technology Process of prostaglandin B2

There total 7 articles about prostaglandin B2 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:

prostaglandin A2 (13345-50-1) → prostaglandin B2 (13367-85-6)

Guidance literature:

With piperidine; In methanol; for 72h;

DOI:10.1021/jm00182a018

Reference yield:

(5Z,13E)-15-hydroxy-9-oxoprosta 5,10,13 trien-1-oic acid (31753-19-2) → prostaglandin B2 (13367-85-6)

Guidance literature:

Multi-step reaction with 5 steps

1: imidazole / dimethylformamide / 18 h / 25 °C

2: 1.) aq. H₂O₂, 1N NaOH, 2.) aluminum amalgam / 1.) methanol, -10-0 deg C, 2 h

3: 83 percent / morphilinosulfotrifluoride / CH₂Cl₂ / 1 h / -78 °C

4: 75 percent / aq. acetic acid, 1N HCl / tetrahydrofuran / 30 h / 25 °C

5: alkaline medium

With 1H-imidazole; hydrogenchloride; sodium hydroxide; aluminium amalgam; dihydrogen peroxide; acetic acid; morpholinosulfur trifluoride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

15α-O-t-butyldimethylsilyl-PGA2 methyl ester (53122-04-6) → prostaglandin B2 (13367-85-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) aq. H₂O₂, 1N NaOH, 2.) aluminum amalgam / 1.) methanol, -10-0 deg C, 2 h

2: 83 percent / morphilinosulfotrifluoride / CH₂Cl₂ / 1 h / -78 °C

3: 75 percent / aq. acetic acid, 1N HCl / tetrahydrofuran / 30 h / 25 °C

4: alkaline medium

With hydrogenchloride; sodium hydroxide; aluminium amalgam; dihydrogen peroxide; acetic acid; morpholinosulfur trifluoride; In tetrahydrofuran; dichloromethane;

upstream raw materials:

prostaglandin A₂

methyl ester of 11-fluoro-11-desoxyprostaglandin E₂

(5Z,13E)-15-hydroxy-9-oxoprosta 5,10,13 trien-1-oic acid

15α-O-t-butyldimethylsilyl-PGA₂ methyl ester

Downstream raw materials:

Prostaglandin B⁽²⁾-p-phenylbenzylester

(Z)-7-[2-((E)-(S)-3-Hydroxy-oct-1-enyl)-5-oxo-cyclopent-1-enyl]-hept-5-enoic acid biphenyl-4-yloxycarbonylmethyl ester

Prostaglandin B⁽²⁾-p-phenylphenacylester

Prostaglandin B⁽²⁾-p-bromphenacylester

Refernces

• 1、 Hirayama,Kurihara,Uekama. "Mechanisms of deceleration by methylated cyclodextrins in the dehydration of prostaglandin E2 and isomerization of prostaglandin A2 in aqueous solution". . p. 5093 - 5101. Retrieved 2007/10/02.
• 2、 Bezuglov, V. V.,Serkov, I. V.,Gafurov, R. G.,Bergel'son, L. D.. "SYNTHESIS OF FLUORODESOXYPROSTAGLANDIN E2". . p. 264 - 266. Retrieved 2007/10/02.