69552-46-1

Basic information

• Product Name: CARBACYCLIN
• Synonyms: 6,9ALPHA-METHYLENE-11ALPHA,15S-DIHYDROXY-PROSTA-5E,13E-DIEN-1-OIC ACID;6A-CARBA-PROSTAGLANDIN I2;carboprostacyclin;6,9-Methanoprostaglandin I2;6a-Carba-prostaglandinI2, CarbocyclicPGI2;(5E)-6a-Carbaprostaglandin 12;5-[(1β,3E,5β,6R)-6β-[(1E,3S)-3-Hydroxy-1-octenyl]-7α-hydroxybicyclo[3.3.0]octane-3-ylidene]pentanoic acid;5-[(2E,3aS,5R,6aβ)-Octahydro-5α-hydroxy-4β-[(1E,3S)-3-hydroxy-1-octenyl]pentalen-2-ylidene]pentanoic acid
• CAS NO: 69552-46-1
• Molecular Formula: C21H34O4
• Molecular Weight: 350.49
• EINECS: 636-209-4
• Mol File: 69552-46-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: 65-67℃
• Boiling Point: 514.8 °C at 760 mmHg
• Flash Point: 279.2 °C
• Appearance: /
• Density: 1.177 g/cm³
• Vapor Pressure: 9.46E-13mmHg at 25°C
• Refractive Index: 1.61
• Storage Temp.: −20°C
• Solubility: Soluble at 20mg/ml in ethanol.
• PKA: 4.77±0.10(Predicted)
• CAS DataBase Reference: CARBACYCLIN(CAS DataBase Reference)
• NIST Chemistry Reference: CARBACYCLIN(69552-46-1)
• EPA Substance Registry System: CARBACYCLIN(69552-46-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 22-36
• WGK Germany: 3
• Hazardous Substances Data: 69552-46-1(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 69552-46-1 differently. You can refer to the following data:
1. 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.
2. 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.

InChI:InChI=1/C21H34O4/c1-2-3-4-8-17(22)10-11-18-19-13-15(7-5-6-9-21(24)25)12-16(19)14-20(18)23/h7,10-11,16-20,22-23H,2-6,8-9,12-14H2,1H3,(H,24,25)/b11-10+,15-7+/t16-,17-,18+,19-,20+/m0/s1

Upstream product

• 94595-91-2 (1R,5S,6S,7R)-3-oxo-6-hydroxymethyl-7-hydroxybicyclo<3.3.0>octane 
• 36969-89-8 dimethyl 2-oxoheptylphosphonate 
• 71846-50-9 (1R,2R,3aS,6aS)-1-((E)-(S)-3-Hydroxy-oct-1-enyl)-5-[5-hydroxy-pent-(E)-ylidene]-octahydro-pentalen-2-ol 
• 102404-75-1 (-)-(5E)-9(O)-methanoprostacyclin methyl ester 11,15-diacetate 
• 71845-98-2 (5E)-6a-carbaprostaglandin I₂ bis(tetrahydropyranyl) ether 
• 69552-55-2 (5E)-6a-carbaprostaglandin I₂ methyl ester 
• 73996-33-5 3α-hydroxy-7-oxo-2β-hydroxymethylbicyclo<3.3.0>octane 3-tetrahydropyranyl ether 
• 87751-96-0 5(S^*)-hydroxy-6α-ethoxycarbonyl-6a-carbaprostaglandin I₁ methyl ester 11,15-bis(tetrahydropyran-2-yl)ether 
• 87751-97-1 5(S^*)-hydroxy-6α-carboxy-6a-carbaprostaglandin I₁ 11,15-bis(tetrahydropyran-2-yl)ether 
• 87752-06-5 5-acetoxy-6α-ethoxycarbonyl-6a-carbaprostaglandin I₁ methyl ester 
• 313998-85-5 ethyl (2E,5E)-9-ethoxycarbonyl-5-(prop-2-enyl)-2,5-nonadienoate 
• 313998-94-6 ethyl (5E,8EZ)-10-hydroxy-6-(prop-2-enyl)deca-5,8-dienoate 
• 2548-87-0 (E)-2-Octenal 
• 70871-23-7 5-[(3aR,4S,5S,6aR)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(R)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid methyl ester 

Downstream Products

• 102491-28-1 (-)-ent-9(O)-methanoprostacyclin 

Relevant articles and documents

Practical synthesis of 6a-carbaprostaglandin I2

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Cross metathesis as a general strategy for the synthesis of prostacyclin and prostaglandin analogues

A cross metathesis (CM) approach has been successfully applied to introduce fully functionalized ω-side chain appendages of various prostacyclin and prostaglandin analogues, resulting in high (E)-selectivities for the C13-C14 double bond and leading to the total syntheses of isocarbacyclin, 15R-TIC, carbacyclin, and PGF2α, and the formal syntheses of 15-deoxy-TIC and PGJ2.

PROSTANOIDS. LII. (+/-)-7,7-DICHLORO-4β-TRIMETHYLSILYLBICYCLOHEPT-3-EN-6-ONE IN THE SYNTHESIS OF PROSTANOIDS. RACEMIC CARBACYCLIN

The products from the Prins reaction of formaldehyde and (+/-)-7,7-dichloro-4β-trimethylsilylbicyclohept-3-en-6-one were isolated and characterized.The optimum conditions were found for the production of the isomeric 2β-acetoxy-6,6(7,7)-dichlorobicyclohept-3-en-7(6)-ones and 2β-acetoxymethyl-3α-acetoxy-6,6(7,7)-dichlorobicyclohept-3-en-7(6)-ones and also (1R,2S,5R,6S,10R)-3,3-dichloro-4-oxo-10-hydroxy(acetoxy)-8-oxatricyclo2,5>undecanes, suitable for the subsequent synthesis of modified prostanoids.An effective scheme for the synthesis of (+/-)-carbacyclin was worked out on the basis of the monoacetates of a series of bicycloheptenones through the corresponding 2β-acetoxymethyl-3α-acetoxybicyclooctan-7-ones.