Dinoprostone

Base Information

• Chemical Name: Dinoprostone
• CAS No.: 363-24-6
• Molecular Formula: C20H32O5
• Molecular Weight: 352.471
• Hs Code.: 29375000
• 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: 363-24-6.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:

• Appearance/Colour: white to pale yellowish-cream powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 66-68 °C
• Refractive Index: 1.6120 (estimate)
• Boiling Point: 530.1 °C at 760 mmHg
• PKA: pKa 4.77± 0.09(H2O,t=25±0.1,I=0.1(NaCl)) (Uncertain)
• Flash Point: 288.5 °C
• PSA: 94.83000
• Density: 1.148 g/cm³
• LogP: 3.25110
• Storage Temp.: −20°C
• Solubility.: ethanol: 1 mg/mL
• Water Solubility.: insoluble
• 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:

99% ^*data from raw suppliers

Prostaglandin E2 ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

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).
• Description: Prostaglandin E2 (363-24-6; PGE2) is an endogenous prostaglandin derived from the action of cyclooxygenase on arachidonic acid. PGE2 has diverse biological actions in the areas of inflammation, cancer, immune modulation, fertility, smooth muscle relaxation and hematopoietic stem cell homeostasis. Prostaglandin E2 acts through four distinct receptors: EP1, EP2, EP3, EP4.
• Uses: The most common and biologically potent of mammalian prostaglandins. Oxytocic; abortifacient. For use in cell culture applications for the study of prostaglandin regulated cell signaling and gene regulation. The most common and most biologically potent of mammalian prostaglandins. Isolated from sheep prostate. Oxytocic; abortifacient.
• Therapeutic Function: Oxytocic, Abortifacient

Technology Process of Dinoprostone

There total 88 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: 98.0%

(Z)-7-((1R,2R,3R)-3-((tert-butyldimethylsilyl)oxy)-2-((S,E)-3-((tert-butyldimethylsilyl)oxy)oct-1-en-1-yl)-5-oxocyclopentyl)hept-5-enoic acid (85610-68-0) → dinoprostone (363-24-6)

Guidance literature:

With hydrogen fluoride; In water; acetonitrile; at 23 ℃;

DOI:10.1016/S0040-4039(00)84486-X

Reference yield: 95.0%

prostaglandin E2 (31753-17-0) → dinoprostone (363-24-6)

Guidance literature:

With water; In tert-butyl methyl ether; at 35 ℃; for 18h; Enzymatic reaction;

DOI:10.1021/jo101806m

Reference yield: 59.0%

5-hexenoic acid (1577-22-6) + C16H26O3 → dinoprostone (363-24-6)

Guidance literature:

With (Z)-2-Butene; C₃₇H₄₀Cl₂N₂ORuS₂; In tetrahydrofuran; at 22 ℃; under 7 Torr; Pressure; Inert atmosphere; Glovebox; Sealed tube;

upstream raw materials:

(-)-7α-hydroxy-6β-(3α-hydroxy-1E-octenyl)-cis-2-oxabicyclo<3.3.0>octan-3-one

all cis 5,8,11,14-eicosatetraenoic acid

prostaglandin E₂

(Z)-7-((1R,2R,3R)-3-((tert-butyldimethylsilyl)oxy)-2-((S,E)-3-((tert-butyldimethylsilyl)oxy)oct-1-en-1-yl)-5-oxocyclopentyl)hept-5-enoic acid

Downstream raw materials:

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

Prostaglandin E⁽²⁾-p-phenylbenzylester

(Z)-7-[(1R,2R,3R)-3-Hydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-5-oxo-cyclopentyl]-hept-5-enoic acid biphenyl-4-yloxycarbonylmethyl ester

(+/-)-prostaglandin E₂ methyl ester

Refernces

• 1、 Miralpeix, Montserrat,Camacho, Mercedes,Lopez-Belmonte, Jesus,Canalias, Francesca,Beleta, Jordi,Palacios, Jose Ma.,Vila, Luis. "Selective induction of cyclo-oxygenase-2 activity in the permanent human endothelial cell line HUV-EC-C: Biochemical and pharmacological characterization". . p. 171 - 180. Retrieved 1997.
• 2、 Yakusheva, L. A.,Myagkova, G. I.,Sarycheva, I. K.,Evstigneeva, R. P.. "ARACHIDONIC ACID AND METHODS FOR ITS ISOLATION FROM NATURAL MATERIALS". . p. 215 - 222. Retrieved 1984.
• 3、 Jenny,Schaeublin,Fritz,Fuhrer. "Total synthesis of prostaglandin D2". . p. 2235 - 2238. Retrieved 1974.
• 4、 Huang, Xiaoqin,Yan, Weili,Gao, Daquan,Tong, Min,Tai, Hsin-Hsiung,Zhan, Chang-Guo. "Structural and functional characterization of human microsomal prostaglandin E synthase-1 by computational modeling and site-directed mutagenesis". . p. 3553 - 3562. Retrieved 2006.
• 5、 Zhu, Kejie,Hu, Sha,Liu, Minjie,Peng, Haihui,Chen, Fen-Er. "Access to a Key Building Block for the Prostaglandin Family via Stereocontrolled Organocatalytic Baeyer–Villiger Oxidation". . p. 9923 - 9927. Retrieved 2019/05/16.
• 6、 Jagusch, Hans,Werner, Markus,Werz, Oliver,Pohnert, Georg. "15-Hydroperoxy-PGE2: Intermediate in Mammalian and Algal Prostaglandin Biosynthesis". supporting information. p. 17641 - 17645. Retrieved 2019/11/13.