16,16-dimethylprostaglandin E2

Base Information

• Chemical Name: 16,16-dimethylprostaglandin E2
• CAS No.: 39746-25-3
• Molecular Formula: C22H36 O5
• Molecular Weight: 380.525
• European Community (EC) Number: 630-974-8
• UNII: M790V82VAC
• DSSTox Substance ID: DTXSID201025748
• Wikidata: Q27070785
• NCI Thesaurus Code: C84850
• Pharos Ligand ID: HR56R9BBF36C
• Metabolomics Workbench ID: 2426
• ChEMBL ID: CHEMBL1221529
• Mol file: 39746-25-3.mol

Synonyms:16,16 Dimethyl PGE2;16,16 Dimethylprostaglandin E2;16,16-Dimethyl-PGE2;16,16-Dimethylprostaglandin E2;E2, 16,16-Dimethylprostaglandin

Chemical Property of 16,16-dimethylprostaglandin E2

Chemical Property:

• Vapor Pressure: 5.66E-14mmHg at 25°C
• Melting Point: -85.6oC
• Boiling Point: 541.3°Cat760mmHg
• Flash Point: 295.2°C
• PSA: 94.83000
• Density: 1.119g/cm³
• LogP: 3.88720
• Storage Temp.: −20°C
• Solubility.: Soluble in methyl acetate
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 380.25627424
• Heavy Atom Count: 27
• Complexity: 535

Purity/Quality:

98%,99%, ^*data from raw suppliers

16,16-Dimethyl Prostaglandin E2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn,Xi
• Hazard Codes: F,Xn,Xi
• Statements: 11-20/21/22-36/37/38-67-66-36
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCC(C)(C)C(C=CC1C(CC(=O)C1CC=CCCCC(=O)O)O)O
• Isomeric SMILES: CCCCC(C)(C)[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O)O
• Description: 16,16-dimethyl PGE2 is a competitive inhibitor of 15-hydroxy PGDH, but it is not a substrate for the enzyme. Because of its resistance to metabolism by 15-hydroxy PGDH, it has a prolonged half-life in vivo. 16,16-dimethyl PGE2 acts as an agonist on most EP receptor subtypes, and has been used experimentally to induce cervical ripening, uterine contraction, and prevent ulceration of the gastric mucosa in rats and dogs. The Kd for activation of isolated EP2 receptors is about 1 nM. 16,16-dimethyl PGE2 can be used to preserve the self-renewal properties while preventing the differentiation of hematopoietic stem cells during expansion in culture.

Technology Process of 16,16-dimethylprostaglandin E2

There total 7 articles about 16,16-dimethylprostaglandin E2 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:

(2S,3R)-2-(1,1-Dimethyl-pentyl)-3-iodomethyl-oxirane → 16,16-dimethyl-PGE2 (39746-25-3)

Guidance literature:

Multi-step reaction with 5 steps

1: KN(SiMe₃)2 / 18-crown-6 / tetrahydrofuran; toluene / 48 h / -78 °C

2: imidazole, Et₃N / dimethylformamide / 4 h / 20 °C

3: 1.6 M nBuLi, CuCN, 1.5 M MeLi / diethyl ether; hexane / 0.33 h / -78 °C

4: pyridinium p-toluenesulfonate / acetone; H₂O / 4 h / Ambient temperature

5: NaCl, CaCl₂, aq. NaOH / tetrahydrofuran; H₂O / porcine pancreatic lipase, pH 7.0-7.2

With 1H-imidazole; sodium hydroxide; n-butyllithium; methyllithium; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; triethylamine; sodium chloride; calcium chloride; 18-crown-6 ether; In tetrahydrofuran; diethyl ether; hexane; water; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1002/(SICI)1521-4184(19989)331:9<279::AID-ARDP279>3.0.CO;2-3

Reference yield:

[(2S,3S)-3-(1,1-Dimethyl-pentyl)-oxiranyl]-methanol → 16,16-dimethyl-PGE2 (39746-25-3)

Guidance literature:

Multi-step reaction with 6 steps

1: PPh₃, imidazole, iPr₂NEt, I₂ / acetonitrile; diethyl ether / 1 h / Ambient temperature

2: KN(SiMe₃)2 / 18-crown-6 / tetrahydrofuran; toluene / 48 h / -78 °C

3: imidazole, Et₃N / dimethylformamide / 4 h / 20 °C

4: 1.6 M nBuLi, CuCN, 1.5 M MeLi / diethyl ether; hexane / 0.33 h / -78 °C

5: pyridinium p-toluenesulfonate / acetone; H₂O / 4 h / Ambient temperature

6: NaCl, CaCl₂, aq. NaOH / tetrahydrofuran; H₂O / porcine pancreatic lipase, pH 7.0-7.2

With 1H-imidazole; sodium hydroxide; n-butyllithium; methyllithium; iodine; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium chloride; calcium chloride; 18-crown-6 ether; In tetrahydrofuran; diethyl ether; hexane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1002/(SICI)1521-4184(19989)331:9<279::AID-ARDP279>3.0.CO;2-3

Reference yield:

(Z)-7-[(1R,2R,3R)-3-Hydroxy-2-((E)-(R)-3-hydroxy-4,4-dimethyl-oct-1-enyl)-5-oxo-cyclopentyl]-hept-5-enoic acid methyl ester (42782-96-7) → 16,16-dimethyl-PGE2 (39746-25-3)

Guidance literature:

With sodium hydroxide; sodium chloride; calcium chloride; In tetrahydrofuran; water; Yield given; porcine pancreatic lipase, pH 7.0-7.2;

DOI:10.1002/(SICI)1521-4184(19989)331:9<279::AID-ARDP279>3.0.CO;2-3

upstream raw materials:

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

(R)-4,4-dimethyl-1-iodo-1(E)-octen-3-ol

[(R)-1-((E)-2-Iodo-vinyl)-2,2-dimethyl-hexyloxy]-trimethyl-silane

(Z)-7-[(1R,2R,3R)-2-((E)-(R)-4,4-Dimethyl-3-trimethylsilanyloxy-oct-1-enyl)-5-oxo-3-trimethylsilanyloxy-cyclopentyl]-hept-5-enoic acid methyl ester

Downstream raw materials:

16,16-Dimethyl-PGA2

Refernces