Carbaprostacyclin;Carba-PGI2

Base Information

• Chemical Name: Carbaprostacyclin;Carba-PGI2
• CAS No.: 69552-46-1
• Molecular Formula: C₂₁H₃₄O₄
• Molecular Weight: 350.499
• European Community (EC) Number: 636-209-4
• Mol file: 69552-46-1.mol

Synonyms:(5E)-6a-carba-prostaglandin I2;6,9-methano PGI2;6,9-methano-PGI2;6,9-methanoprostaglandin I2;6a-carba-PGI2;9alpha-deoxy-9alpha-methylene-PGI2;carba PGX;carba-prostacyclin;carbacyclin;carbacycline;carbaprostacyclin;carboprostacyclin;carboprostacyclin, (3aS-(2Z,3aalpha,4alpha,(1E,3R*),5beta,6aalpha))-isomer;carboprostacyclin, monosodium salt

Chemical Property of Carbaprostacyclin;Carba-PGI2

Chemical Property:

• Vapor Pressure: 9.46E-13mmHg at 25°C
• Melting Point: 65-67℃
• Refractive Index: 1.61
• Boiling Point: 514.8 °C at 760 mmHg
• PKA: 4.77±0.10(Predicted)
• Flash Point: 279.2 °C
• PSA: 77.76000
• Density: 1.177 g/cm³
• LogP: 4.07210
• Storage Temp.: −20°C
• Solubility.: Soluble at 20mg/ml in ethanol.
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 350.24570956
• Heavy Atom Count: 25
• Complexity: 482

Purity/Quality:

99% ^*data from raw suppliers

Carbacyclin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC(C=CC1C(CC2C1CC(=CCCCC(=O)O)C2)O)O
• Uses: Carbacyclin is a stable analog of PGI2. When infused in rabbits or dogs, it inhibits ex vivo platelet aggregation, but the effect persists only 10 minutes after termination of the infusion. Carbacyclin is a stable analog of PGI2. Carbacyclin inhibits platelet aggregation with 10% of the molar potency exhibited by PGI2. The ED50 of Carbacyclin for the in vitro inhibition of ADP-induced platelet aggregation in human PRP is 47 nM. It was also shown to effect terminal differentiation of preadipose into adipose cells and enhance the expression of angiotensinogen and adipose fatty acid binding protein with an EC50 of about 0.5 μM. Carbacyclin acts as a converter of human white to bright adipocytes. Also used in the treatment of high-risk acute lymphoblastic leukemia potentiating the activity of anti-cancer therapeutics.

Technology Process of Carbaprostacyclin;Carba-PGI2

There total 142 articles about Carbaprostacyclin;Carba-PGI2 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: 100.0%

(5E)-6a-carbaprostaglandin I2 methyl ester (69552-55-2) → (5E)-carba-PGI2 (69552-46-1)

Guidance literature:

With sodium hydroxide; In methanol; at 0 ℃; for 13h;

DOI:10.1248/cpb.39.309

Reference yield: 79.0%

(5E)-6a-carbaprostaglandin I2 bis(tetrahydropyranyl) ether (71845-98-2) → (5E)-carba-PGI2 (69552-46-1)

Guidance literature:

In tetrahydrofuran; water; acetic acid; at 45 ℃; for 3h;

DOI:10.1016/S0040-4020(01)87443-3

Reference yield: 57.0%

(1R,2R,3aS,6aS)-1-((E)-(S)-3-Hydroxy-oct-1-enyl)-5-[5-hydroxy-pent-(E)-ylidene]-octahydro-pentalen-2-ol (71846-50-9) → (5E)-carba-PGI2 (69552-46-1)

Guidance literature:

With oxygen; sodium hydrogencarbonate; platinum; In water; acetone; at 57 ℃; for 2h;

DOI:10.1021/ja00249a068

upstream raw materials:

3α-hydroxy-7-oxo-2β-hydroxymethylbicyclo<3.3.0>octane 3-tetrahydropyranyl ether

(5E)-6a-carbaprostaglandin I₂ methyl ester

(5E)-6a-carbaprostaglandin I₂ bis(tetrahydropyranyl) ether

(-)-(5E)-9(O)-methanoprostacyclin methyl ester 11,15-diacetate

Downstream raw materials:

(-)-ent-9(O)-methanoprostacyclin

Refernces

• 1、 Konishi, Yoshitaka,Kawamura, Masanori,Iguchi, Yoichi,Arai, Yoshinobu,Hayashi, Masaki. "Facile synthesis of 6a-carbaprostaglandin I2". . p. 4391 - 4399. Retrieved 2015/01/08.
• 2、 Okamoto,Subburaj,Sato. "Highly stereocontrolled synthesis of carbacyclin from acyclic starting materials via Ti(II)-Mediated tandem cyclization [10]". . p. 11244 - 11245. Retrieved 2007/10/03.