Unoprostone

Base Information

• Chemical Name: Unoprostone
• CAS No.: 120373-36-6
• Molecular Formula: C₂₂H₃₈O₅
• Molecular Weight: 382.541
• European Community (EC) Number: 800-615-1
• UNII: 6X4F561V3W
• DSSTox Substance ID: DTXSID80905120
• Nikkaji Number: J561.802I
• Wikipedia: Unoprostone
• Wikidata: Q4859684
• NCI Thesaurus Code: C76904
• Metabolomics Workbench ID: 2543
• ChEMBL ID: CHEMBL1201407
• Mol file: 120373-36-6.mol

Synonyms:Unoprostone;120373-36-6;Unoprostone [MI];Unoprostone [INN];13,14-dihydro-15-keto-20-ethyl PGF2alpha;UNII-6X4F561V3W;CHEBI:39455;6X4F561V3W;Unoprostone (INN);(+)-(Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl)-5-heptenoic acid;(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]hept-5-enoic acid;(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]hept-5-enoic acid;9,11-dihydroxy-15-oxo-20a,20b-dihomoprost-5Z-en-1-oic acid;5-Heptenoic acid,7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]-, (5Z)-;13,14-Dihydro-15-keto-20-ethyl prostaglandin f2alpha;(5Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl)hept-5-enoic acid;D09SRR;UNOPROSTONE [VANDF];UNOPROSTONE [WHO-DD];SCHEMBL194651;CHEMBL1201407;DTXSID80905120;(5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-(3-oxodecyl)cyclopentyl]-5-heptenoic acid;HMS3648D22;LMFA03010204;AKOS015950955;DB06826;HY-106916;CS-0026907;13,14-dihydro-15-keto-20-ethyl-PGF2-alpha;D08661;EN300-21702552;SR-01000946492;J-004324;J-525150;Q4859684;SR-01000946492-1;(5Z,9alpha,11alpha)-9,11-dihydroxy-15-oxo-20a,20b-dihomoprost-5-en-1-oic acid;9.alpha.,11.alpha.-Dihydroxy-13,14-dihydro-15-oxo-20a,20b-dihomoprost-5-en-1-oic acid

Chemical Property of Unoprostone

Chemical Property:

• Vapor Pressure: 5.16E-15mmHg at 25°C
• Boiling Point: 562.9°Cat760mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 308.3°C
• PSA: 94.83000
• Density: 1.069g/cm³
• LogP: 4.25530
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 15
• Exact Mass: 382.27192431
• Heavy Atom Count: 27
• Complexity: 460

Purity/Quality:

98% ^*data from raw suppliers

Unoprostane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCC(=O)CCC1C(CC(C1CC=CCCCC(=O)O)O)O
• Isomeric SMILES: CCCCCCCC(=O)CC[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O
• Recent NIPH Clinical Trials: Topical Isopropyl Unoprostone for Rhegmatogenous Retinal Detachment: Pilot Study
• Uses: Unoprostane is a protectant against retinal degeneration in S334ter rhodopsin mutant rats. Neuroprotective agent.

Technology Process of Unoprostone

There total 8 articles about Unoprostone 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:

(8aR,9R,10R,11aS,5Z)-9-(3-oxodecyl-10-hydroxy)-4,5,8,8a,9,10,11,11a-octahydrocyclopenta[b]oxecin-2(3H)-one → unoprostone (120373-36-6)

Guidance literature:

With water; potassium hydroxide; In isopropyl alcohol; for 2h; Reflux;

Reference yield:

(3aR,4R,5R,6aS)-4-(3-(tert-butyldimethylsilyloxy)decyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-ol → unoprostone (120373-36-6)

Guidance literature:

Multi-step reaction with 6 steps

1: potassium tert-butylate / tetrahydrofuran / 4 h / -20 °C

2: 2,2'-dipyridyldisulphide; triphenylphosphine / 5,5-dimethyl-1,3-cyclohexadiene / 19 h / 20 - 80 °C / Inert atmosphere

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 50 °C

4: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; sodium hydrogencarbonate; sodium hypochlorite / toluene; hexane; water; ethyl acetate / 0.17 h / 0 °C

5: toluene-4-sulfonic acid / methanol / 3 h / 20 °C

6: potassium hydroxide; water / isopropyl alcohol / 2 h / Reflux

With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 2,2'-dipyridyldisulphide; potassium tert-butylate; tetrabutyl ammonium fluoride; water; sodium hydrogencarbonate; toluene-4-sulfonic acid; triphenylphosphine; potassium bromide; potassium hydroxide; In tetrahydrofuran; methanol; 5,5-dimethyl-1,3-cyclohexadiene; hexane; water; ethyl acetate; isopropyl alcohol; toluene; 1: |Wittig Olefination;

Reference yield:

(3aR,4R,5R,6aS)-4-(3-(tert-butyldimethylsilyloxy)decyl)-5-(tetrahydro-2H-pyran-2-yloxy)-hexahydro-2H-cyclopenta[b]furan-2-one → unoprostone (120373-36-6)

Guidance literature:

Multi-step reaction with 7 steps

1: diisobutylaluminium hydride / toluene; hexane / -70 °C

2: potassium tert-butylate / tetrahydrofuran / 4 h / -20 °C

3: 2,2'-dipyridyldisulphide; triphenylphosphine / 5,5-dimethyl-1,3-cyclohexadiene / 19 h / 20 - 80 °C / Inert atmosphere

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 50 °C

5: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; sodium hydrogencarbonate; sodium hypochlorite / toluene; hexane; water; ethyl acetate / 0.17 h / 0 °C

6: toluene-4-sulfonic acid / methanol / 3 h / 20 °C

7: potassium hydroxide; water / isopropyl alcohol / 2 h / Reflux

With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 2,2'-dipyridyldisulphide; potassium tert-butylate; tetrabutyl ammonium fluoride; water; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; triphenylphosphine; potassium bromide; potassium hydroxide; In tetrahydrofuran; methanol; 5,5-dimethyl-1,3-cyclohexadiene; hexane; water; ethyl acetate; isopropyl alcohol; toluene; 2: |Wittig Olefination;

Refernces

• 1、 -. "PROCESSES AND INTERMEDIATES FOR THE PREPARATIONS OF ISOMER FREE PROSTAGLANDINS". . . Retrieved 2015/02/25.