Prostaglandin F2alpha methyl ester

Base Information

• Chemical Name: Prostaglandin F2alpha methyl ester
• CAS No.: 33854-16-9
• Molecular Formula: C21H36O5
• Molecular Weight: 368.514
• UNII: C289Y64HRB
• DSSTox Substance ID: DTXSID501037318
• Wikidata: Q76293767
• Metabolomics Workbench ID: 2465
• ChEMBL ID: CHEMBL1519030
• Mol file: 33854-16-9.mol

Synonyms:15-Mt-PGF2alpha;dinoprost methyl ester;PGF2 methyl ester;PGF2alpha methyl ester;prostaglandin F2 methyl ester;prostaglandin F2 methyl ester, (5Z,8beta,9alpha,11alpha,12alpha,13E,15R)-isomer;prostaglandin F2 methyl ester, (5Z,8beta,9alpha,11alpha,12alpha,13E,15S)-isomer;prostaglandin F2 methyl ester, (5Z,8beta,9alpha,11beta,12alpha,13E,15R)-isomer;prostaglandin F2 methyl ester, (5Z,8beta,9alpha,11beta,12alpha,13E,15S)-isomer;prostaglandin F2 methyl ester, (5Z,8beta,9beta,11alpha,12alpha,13E,15R)-isomer;prostaglandin F2 methyl ester, (5Z,8beta,9beta,11alpha,12alpha,13E,15S)-isomer;prostaglandin F2 methyl ester, (5Z,8beta,9beta,11beta,12alpha,13E,15R)-isomer;prostaglandin F2 methyl ester, (5Z,8beta,9beta,11beta,12alpha,13E,15S)-isomer;prostaglandin F2 methyl ester, (5Z,9alpha,11beta,13E,15S)-isomer

Chemical Property of Prostaglandin F2alpha methyl ester

Chemical Property:

• Vapor Pressure: 2.33E-12mmHg at 25°C
• Refractive Index: 1.6120 (estimate)
• Boiling Point: 494.2°Cat760mmHg
• Flash Point: 161.9°C
• PSA: 86.99000
• Density: 1.107g/cm³
• LogP: 3.13130
• Storage Temp.: −20°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 13
• Exact Mass: 368.25627424
• Heavy Atom Count: 26
• Complexity: 446

Purity/Quality:

98%,99%, ^*data from raw suppliers

Prostaglandin F2α methyl ester ~5 mg/mL in methyl acetate, ≥95% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 11-36-66-67
• Safety Statements: 16-26-29-33

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC1C(CC(C1CC=CCCCC(=O)OC)O)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)OC)O)O)O

Technology Process of Prostaglandin F2alpha methyl ester

There total 77 articles about Prostaglandin F2alpha methyl ester 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: 95.0%

prostaglandin E2 (31753-17-0) → (+)-prostaglandin F2α (33854-16-9)

Guidance literature:

With diisobutyl(2,6-di-tert-butyl-4- methylphenoxy)aluminum; In toluene; at -78 - -20 ℃; for 3.5h;

DOI:10.1246/bcsj.54.3033

Reference yield: 85.0%

11,15-O-bis(tert-butyldimethylsilyl)PGF2α methyl ester (66602-11-7) → (+)-prostaglandin F2α (33854-16-9)

Guidance literature:

In tetrahydrofuran; water; acetic acid; at 55 ℃; for 1.5h;

DOI:10.1016/S0040-4039(00)85895-5

Reference yield: 17.0%

PGH2 methyl ester (63942-75-6) → (+)-prostaglandin F2α (33854-16-9) + prostaglandin D2 methyl ester (49852-81-5) + prostaglandin E2 (31753-17-0) + (5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoic acid methyl ester (79171-56-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; at 19 ℃; for 3h;

DOI:10.1021/ja00408a072

upstream raw materials:

(5Z,13E)-9α,11α-bis(tetrahydro-2-pyranyloxy)-15S-hydroxyprosta-5,13-dienoic acid methyl ester

15-epi-PGF_2α

(S)-(2-hydroxyheptyl)triphenylphosphonium iodide

prostaglandin E₂

Downstream raw materials:

Prostaglandin F_2α 11,15-Dibenzoate methyl ester

Prostaglandin F_2α tribenzoate methyl ester

methyl 11α,15(S)-bis<<(1,1-dimethylethyl)diphenylsilyl>oxy>-6,9α-epoxyprosta-6,13(E)-dien-1-oate

methyl 11α,15(S)-bis<<(1,1-dimethylethyl)diphenylsilyl>oxy>-6,9α-epoxy-6-methoxyprost-13(E)-en-1-oate

Refernces

• 1、 Martinez,Muchowski,Velarde. "Highly stereoselective synthesis of 9 epi prostaglandin F2(α) and 11 epi prostaglandin F2(α) by the aluminum hydride reduction of prostaglandin E2 and 11 epi prostaglandin E2 derivatives". . p. 1087 - 1089. Retrieved 1977.
• 2、 Abian,Gelpi. "High-performance liquid chromatography/thermospray mass spectrometry of some prostaglandins of time F series". . p. 608 - 616. Retrieved 1995.
• 3、 -. "Cyclopentane 1-hydroxy alkyl or alkenyl-2-one or 2-hydroxy derivatives as therapeutic agents". . . Retrieved 2008/06/13.
• 4、 Sato, Yoshihiro,Takimoto, Masanori,Mori, Miwako. "Total Synthesis of Prostaglandin F2α via Nickel-Promoted Stereoselective Cyclization of 1,3-Diene and Aldehyde". . p. 734 - 736. Retrieved 2007/10/03.