Dinoprostone

Base Information

• Chemical Name: Dinoprostone
• CAS No.: 22230-04-2
• Molecular Formula: C₂₀H₃₂O₅
• Molecular Weight: 352.471
• European Community (EC) Number: 206-656-6
• NSC Number: 196514,165560
• UNII: K7Q1JQR04M
• DSSTox Substance ID: DTXSID4022947,DTXSID00859353
• Nikkaji Number: J9.243F
• Wikipedia: Prostaglandin E2,Prostaglandin_E2
• Wikidata: Q416554
• NCI Thesaurus Code: C61727,C112043,C157134
• RXCUI: 3478
• Pharos Ligand ID: GCFTHMVTVAZN
• Metabolomics Workbench ID: 2373
• ChEMBL ID: CHEMBL548
• Mol file: 22230-04-2.mol

Synonyms:alpha, PGE2;alpha, Prostaglandin E2;Dinoprostone;E2 alpha, Prostaglandin;E2, Prostaglandin;E2alpha, Prostaglandin;Gel, Prepidil;PGE2;PGE2 alpha;PGE2alpha;Prepidil Gel;Prostaglandin E2;Prostaglandin E2 alpha;Prostaglandin E2alpha;Prostenon

Chemical Property of Dinoprostone

Chemical Property:

• XLogP3: 2.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 352.22497412
• Heavy Atom Count: 25
• Complexity: 469

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCC(C=CC1C(CC(=O)C1CC=CCCCC(=O)O)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O)O
• Recent ClinicalTrials: Preoperative Vaginal Dinoprostone Versus Misoprostone in Abdominal Myomectomy
• Recent EU Clinical Trials: COok's ballon versus dinoprostone for Labor Induction of term pregnancies with fetal GROWth restriction (COLIGROW study).

Technology Process of Dinoprostone

There total 25 articles about Dinoprostone 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:

(5Z,8R,9R,11S,12S,13E,15R)-11,15-bis-(tert-butyldimethylsilyloxy)-9-oxoprosta-5,13-dienoic acid (303015-41-0) → ent-prostaglandin E2 (363-24-6,13164-28-8,22230-04-2,27415-25-4,31660-13-6,31660-17-0,36150-00-2,37495-69-5,37785-90-3,38310-90-6,38873-82-4,39265-67-3,39648-42-5,54324-09-3,54324-10-6,57759-80-5,57759-81-6,63179-97-5,65026-02-0,65085-69-0,70051-84-2,85548-91-0) + ent-15-E2t-isoprostane

Guidance literature:

(5Z,8R,9R,11S,12S,13E,15R)-11,15-bis-(tert-butyldimethylsilyloxy)-9-oxoprosta-5,13-dienoic acid; With pyridine; hydrogen fluoride; In tetrahydrofuran; water; acetonitrile; at 20 ℃; for 6h;

With potassium acetate; In methanol; at 20 ℃; for 96h;

DOI:10.1016/S0040-4020(00)00531-7

Reference yield:

(Z)-7-[(1R,2S,3S,5R)-5-Acetoxy-3-hydroxy-2-((E)-(R)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid ethyl ester (214748-78-4) → ent-prostaglandin E2 (363-24-6,13164-28-8,22230-04-2,27415-25-4,31660-13-6,31660-17-0,36150-00-2,37495-69-5,37785-90-3,38310-90-6,38873-82-4,39265-67-3,39648-42-5,54324-09-3,54324-10-6,57759-80-5,57759-81-6,63179-97-5,65026-02-0,65085-69-0,70051-84-2,85548-91-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 82 percent / imidazole; DMAP / CH₂Cl₂ / 24 h / 20 °C

2.1: 92 percent / LiOH*H₂O / tetrahydrofuran; H₂O; methanol / 24 h / 20 °C

3.1: 95 percent / Dess-Martin periodinate / CH₂Cl₂ / 20 h / 20 °C

4.1: HF; pyridine / H₂O; tetrahydrofuran; acetonitrile / 6 h / 20 °C

4.2: KOAc / methanol / 96 h / 20 °C

With pyridine; 1H-imidazole; dmap; lithium hydroxide; hydrogen fluoride; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 1.1: Substitution / 2.1: Hydrolysis / 3.1: Oxidation / 4.1: Hydrolysis / 4.2: Isomerization;

DOI:10.1016/S0040-4020(00)00531-7

Reference yield:

(5Z,8R,9R,11S,12S,13E,15R)-11,15-bis-(tert-butyldimethylsilyloxy)-9-hydroxyprosta-5,13-dienoic acid (303015-43-2) → ent-prostaglandin E2 (363-24-6,13164-28-8,22230-04-2,27415-25-4,31660-13-6,31660-17-0,36150-00-2,37495-69-5,37785-90-3,38310-90-6,38873-82-4,39265-67-3,39648-42-5,54324-09-3,54324-10-6,57759-80-5,57759-81-6,63179-97-5,65026-02-0,65085-69-0,70051-84-2,85548-91-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / Dess-Martin periodinate / CH₂Cl₂ / 20 h / 20 °C

2.1: HF; pyridine / H₂O; tetrahydrofuran; acetonitrile / 6 h / 20 °C

2.2: KOAc / methanol / 96 h / 20 °C

With pyridine; hydrogen fluoride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; water; acetonitrile; 1.1: Oxidation / 2.1: Hydrolysis / 2.2: Isomerization;

DOI:10.1016/S0040-4020(00)00531-7

upstream raw materials:

(5Z,8R,9R,11S,12S,13E,15R)-11,15-bis-(tert-butyldimethylsilyloxy)-9-oxoprosta-5,13-dienoic acid

(Z)-7-[(1R,2S,3S,5R)-5-Acetoxy-3-hydroxy-2-((E)-(R)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid ethyl ester

(5Z,8R,9R,11S,12S,13E,15R)-11,15-bis-(tert-butyldimethylsilyloxy)-9-hydroxyprosta-5,13-dienoic acid

ethyl (5Z,8R,9R,11S,12S,13E,15R)-9-acetoxy-11,15-bis-(tert-butyldimethylsilyloxy)prosta-5,13-dienoate

Downstream raw materials:

(+/-)-prostaglandin E₂ methyl ester