Prostaglandin F2alpha-1,15 lactone

Base Information

• Chemical Name: Prostaglandin F2alpha-1,15 lactone
• CAS No.: 55314-49-3
• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.472
• Mol file: 55314-49-3.mol

Synonyms:Prostaglandin F2alpha-1,15 lactone;PGF2-alpha 1,15-lactone;Prostaglandin F2-alpha 1,15-lactone;BRN 1262372;55314-49-3;U 47473;(1R,2E,4S,10E,13R,14S,16R)-14,16-dihydroxy-4-pentyl-5-oxabicyclo[11.3.0]hexadeca-2,10-dien-6-one;Prosta-5,13-dien-1-oic acid, 9,11,15-trihydroxy-, lambda-lactone, (5Z,9-alpha,11-alpha,13E,15S)-;Prostaglandin F2alpha 1,15-lactone;Prostaglandin F2 alpha 1,15-lactone;LS-125837;9ALPHA,11ALPHA,15S-TRIHYDROXY-PROSTA-5Z,13E-DIEN-1-OICACID,1,15-LACTONE

Chemical Property of Prostaglandin F2alpha-1,15 lactone

Chemical Property:

• Vapor Pressure: 3.58E-13mmHg at 25°C
• Boiling Point: 524.1 °C at 760 mmHg
• Flash Point: 180.9 °C
• PSA: 66.76000
• Density: 1.051 g/cm³
• LogP: 3.52280
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 336.23005950
• Heavy Atom Count: 24
• Complexity: 443

Purity/Quality:

99% ^*data from raw suppliers

Prostaglandin F2α 1,15-lactone ≥99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC1C=CC2C(CC=CCCCC(=O)O1)C(CC2O)O
• Isomeric SMILES: CCCCC[C@H]1/C=C/[C@@H]2[C@@H](C/C=C/CCCC(=O)O1)[C@H](C[C@H]2O)O
• Description: PGF2α 1,15-lactone is a lipid-soluble internal ester of PGF2α. Hydrolysis of the lactone readily produces free PGF2α in plasma. In rhesus monkeys, a total dose of 15 mg of PGF2α 1,15-lactone terminates early pregnancy, whereas PGF2α is ineffective.

Technology Process of Prostaglandin F2alpha-1,15 lactone

There total 2 articles about Prostaglandin F2alpha-1,15 lactone 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:

(3E,11Z)-(1R,2R,5S,14R,15S)-17-Butyl-5-pentyl-6,16,18-trioxa-17-bora-tricyclo[13.3.1.02,14]nonadeca-3,11-dien-7-one (62410-92-8) → PGF2α 1,15-lactone (55314-49-3)

Guidance literature:

With dihydrogen peroxide; sodium hydrogencarbonate; In tetrahydrofuran; at 25 ℃; for 0.5h; Yield given;

DOI:10.1021/jm00362a001

Reference yield:

→ PGF2α 1,15-lactone (55314-49-3)

Guidance literature:

Bis-THP-Ether VII, AcOH, THF, H2O;

Reference yield:

PGF2α 1,15-lactone (55314-49-3) → PGD2 1,15-lactone (62410-98-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / imidazole / dimethylformamide / 1 h / 0 °C

2: 92 percent / pyridine hydrochloride / CH₂Cl₂ / 18 h / 25 °C

3: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 25 °C

4: H₂CrO₄, H₂SO₄ / acetone / 1.25 h / -30 - -20 °C

5: 243 mg / AcOH / H₂O; tetrahydrofuran / 3 h / 40 °C

With 1H-imidazole; sulfuric acid; tetrabutyl ammonium fluoride; pyridine hydrochloride; chromic acid; acetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm00360a003

upstream raw materials:

(3E,11Z)-(1R,2R,5S,14R,15S)-17-Butyl-5-pentyl-6,16,18-trioxa-17-bora-tricyclo[13.3.1.0^2,14]nonadeca-3,11-dien-7-one

Downstream raw materials:

PGD₂ 1,15-lactone

PGE2-1,15-lactone

Refernces