7-[3-Hydroxy-2-(4-hydroxy-4-methyloct-1-enyl)-5-oxocyclopentyl]heptanoic acid

Base Information

• Chemical Name: 7-[3-Hydroxy-2-(4-hydroxy-4-methyloct-1-enyl)-5-oxocyclopentyl]heptanoic acid
• CAS No.: 112137-89-0
• Molecular Formula: C₂₁H₃₆O₅
• Molecular Weight: 368.514
• European Community (EC) Number: 663-428-2
• Mol file: 112137-89-0.mol

Synonyms:112137-89-0;BCP32053;FT-0672418

Chemical Property of 7-[3-Hydroxy-2-(4-hydroxy-4-methyloct-1-enyl)-5-oxocyclopentyl]heptanoic acid

Chemical Property:

• Vapor Pressure: 7.86E-14mmHg at 25°C
• Boiling Point: 538.3°C at 760 mmHg
• PKA: 4.77±0.10(Predicted)
• Flash Point: 15.00 F
• PSA: 94.83000
• Density: 1.118g/cm³
• LogP: 3.86520
• Storage Temp.: −20°C
• Solubility.: Chloroform
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 13
• Exact Mass: 368.25627424
• Heavy Atom Count: 26
• Complexity: 473

Purity/Quality:

97% ^*data from raw suppliers

Misoprostol acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 45-60-61-25-36/37/38
• Safety Statements: 53-22-36/37/39-45-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC(C)(CC=CC1C(CC(=O)C1CCCCCCC(=O)O)O)O
• Description: Misoprostol is a prostaglandin E1 analog with agonist activity mediated by EP2, EP3, and EP4 receptors. It has been shown to inhibit the formation of gastric lesions in rats (ED50 = 0.31 μg/kg), inhibit superoxide generation in human neutrophils (EC50 = 0.35 μM), and relax fetal rabbit ductus arteriosus (EC50 = 0.36 nM) in a concentration dependent manner. Misoprostol is commonly used in clinical medicine for the prevention of peptic ulcer disease. It has also been used in conjunction with mifepristone (RU-486; ) for the oral induction of first trimester abortion. Misoprostol contains a C-1 methyl ester and is readily absorbed and rapidly hydrolyzed in humans to the active free acid.
• Uses: Misoprostol Acid is a prostaglandin E1 analog with agonist activity mediated by EP2, EP3, and EP4 receptors. It has been shown to inhibit the formation of gastric lesions in rats (ED50 = 0.31 μg/kg), inhibit superoxide generation in human neutrophils (EC50 = 0.35 μM), and relax fetal rabbit ductus arteriosus (EC50 = 0.36 nM) in a concentration dependent manner. Misoprostol is commonly used in clinical medicine for the prevention of peptic ulcer disease. It has also been used in conjunction with mifepristone (RU-486; ) for the oral induction of first trimester abortion. Misoprostol contains a C-1 methyl ester and is readily absorbed and rapidly hydrolyzed in humans to the active free acid. A metabolite of Misoprostol. Cytoprotective PGE1 analog that prevents NSAID-induced gastric ulceration A cytoprotective prostaglandin PGE1 analogue.

Technology Process of 7-[3-Hydroxy-2-(4-hydroxy-4-methyloct-1-enyl)-5-oxocyclopentyl]heptanoic acid

There total 1 articles about 7-[3-Hydroxy-2-(4-hydroxy-4-methyloct-1-enyl)-5-oxocyclopentyl]heptanoic acid 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:

4-methyl-4-trimethylsilyloxyl-1-octyne (66792-28-7) + 4-(Trimethylsilyloxy)-2-(6-carbotrimethylsiloxyhexyl)-cyclopent-2-en-1-on (52418-95-8) → misoprostol acid (112137-89-0,66792-31-2)

Guidance literature:

Multistep reaction;

DOI:10.1021/jo00412a005

Reference yield: 72.0%

O-phenylhydroxylamine (4846-21-3) + Misoprostol free acid (112137-89-0,66792-31-2) → 7-((1R,2R,3R)-3-hydroxy-2-((E)-4-hydroxy-4-methyloct-1-enyl)-5-oxocyclopentyl)-N-phenoxyheptanamide

Guidance literature:

O-phenylhydroxylamine; Misoprostol free acid; With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; at -10 ℃; for 0.05h; Inert atmosphere;

With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; dichloromethane; at 20 ℃; for 14h; Inert atmosphere;

Reference yield: 58.0%

p-benzoylaminophenol (15457-50-8) + Misoprostol free acid (112137-89-0,66792-31-2) → 4-benzamidophenyl-7-((1R,2R,3R)-3-hydroxy-2-((E)-4-hydroxy-4-methyloct-1-en-1-yl)-5-oxocyclopentyl)heptanoate

Guidance literature:

p-benzoylaminophenol; Misoprostol free acid; With dmap; In dichloromethane; acetic acid methyl ester; at -10 ℃; for 0.05h; Inert atmosphere;

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; acetic acid methyl ester; at 20 ℃; for 14h; Inert atmosphere;

upstream raw materials:

4-methyl-4-trimethylsilyloxyl-1-octyne

4-(Trimethylsilyloxy)-2-(6-carbotrimethylsiloxyhexyl)-cyclopent-2-en-1-on