PGE2 methyl ester

Base Information

• Chemical Name: PGE2 methyl ester
• CAS No.: 31753-17-0
• Molecular Formula: C21H34 O5
• Molecular Weight: 366.498
• Mol file: 31753-17-0.mol

Synonyms:PGE2 methyl ester;prostaglandin E2 methyl ester;prostaglandin E2 methyl ester, (5Z,11alpha,13E,15R)-isomer;prostaglandin E2 methyl ester, (5Z,8beta,11alpha,12alpha,13E,15R)-isomer;prostaglandin E2 methyl ester, (5Z,8beta,11alpha,12alpha,13E,15S)-isomer;prostaglandin E2 methyl ester, (5Z,8beta,11beta,12alpha,13E,15R)-isomer;prostaglandin E2 methyl ester, (5Z,8beta,11beta,12alpha,13E,15S)-isomer

Chemical Property of PGE2 methyl ester

Chemical Property:

• Vapor Pressure: 9.11E-12mmHg at 25°C
• Boiling Point: 492.5°C at 760 mmHg
• Flash Point: 162.1°C
• PSA: 83.83000
• Density: 1.103g/cm³
• LogP: 3.33950
• Storage Temp.: −20°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 13
• Exact Mass: 366.24062418
• Heavy Atom Count: 26
• Complexity: 483

Purity/Quality:

99% ^*data from raw suppliers

Prostaglandin E2 methyl ester ≥98% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36/37/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC1C(CC(=O)C1CC=CCCCC(=O)OC)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1C/C=C/CCCC(=O)OC)O)O
• Description: Prostaglandin E2 methyl ester (PGE2 methyl ester) is an analog of PGE2 with enhanced lipid solubility. PGE2 is one of the primary cyclooxygenase products of arachidonic acid and one of the most widely investigated PGs. Its activity influences inflammation, fertility and parturition, gastric mucosal integrity, and immune modulation. The effects of PGE2 are transduced by at least four distinct receptors designated EP1, EP2, EP3, and EP4. Affinity constants (Kd) values of PGE2 for these receptors range from 1-10 nM depending on the receptor subtype and tissue.

Technology Process of PGE2 methyl ester

There total 105 articles about PGE2 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: 100.0%

methyl (5Z,13E,15S)-11α,15-bis(dimethyl-t-butylsilyloxy)-9-oxoprosta-5,13-dienoate (66602-10-6,73712-05-7,78856-48-1,78856-50-5,104012-06-8) → (+/-)-prostaglandin E2 methyl ester (23453-26-1,31660-08-9,31687-35-1,31753-17-0,31753-18-1,37495-70-8,37495-91-3,38310-89-3,38873-84-6,39645-55-1,41416-98-2,53275-46-0,53275-48-2,53275-57-3,58691-24-0,62446-69-9,62446-70-2,73712-07-9,104012-07-9,126722-04-1)

Guidance literature:

With hydrogen fluoride; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1039/P19810002049

Reference yield: 98.0%

11,15-bis(o-tert-butyldimethylsilyl) PGE2 methyl ester (66602-10-6) → prostaglandin E2 (31753-17-0)

Guidance literature:

With pyridine; hydrogen fluoride; at 24 ℃; for 3h;

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

Reference yield: 98.0%

(-)-(3a'S,3''S,5'R,6'R,6a'S)-methyl (5Z)-7-<6'<(1''E)-3''-hydroxy-1''-octenyl>-2',2'-dimethyl-3a',5',6',6a'-tetrahydro-4'H-cyclopenta-1',3'-dioxol-5'-yl>-5-heptenoate (103904-99-0) → prostaglandin E2 (31753-17-0)

Guidance literature:

With aluminum amalgam; In tetrahydrofuran; water;

DOI:10.1021/ja00278a065

upstream raw materials:

(S)-3-(1-ethoxy-ethoxy)-1t-iodo-oct-1-ene

(Z)-7-[(R)-5-Oxo-3-(tetrahydro-pyran-2-yloxy)-cyclopent-1-enyl]-hept-5-enoic acid methyl ester

(1E)-iodo-(3S)-(tetrahydro-2H-pyran-2-yloxy)-1-octene

PGH₂ methyl ester

Downstream raw materials:

(+)-prostaglandin F_2α

dinoprostone

(Z)-7-[(1S,2R)-2-((E)-(R)-3-Hydroxy-oct-1-enyl)-5-oxo-cyclopent-3-enyl]-hept-5-enoic acid methyl ester

(-)-11α-acetylthio-11-deoxy-11α-homoprostaglandin E₂ acetate methyl ester

Refernces

• 1、 Fuerstner, Alois,Mathes, Christian. "Alkyne cross metathesis reactions of extended scope". . p. 221 - 223. Retrieved 2007/10/03.
• 2、 Lee,Angulo,Ghazal,Janda. "Soluble-polymer supported synthesis of a prostanoid library: identification of antiviral activity.". . p. 1859 - 1862. Retrieved 2008/02/11.