69609-77-4

Basic information

• Product Name: (5Z)-6A-CARBAPROSTAGLANDIN I2
• Synonyms: 5-CIS CARBAPROSTACYCLIN;6,9ALPHA-METHYLENE-11ALPHA,15S-DIHYDROXY-PROSTA-5Z,13E-DIEN-1-OIC ACID;(5Z)-6A-CARBAPROSTAGLANDIN I2
• CAS NO: 69609-77-4
• Molecular Formula: C21H34O3
• Molecular Weight: 334.49
• Mol File: 69609-77-4.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 514.8±50.0 °C(Predicted)
• Appearance: /
• Density: 1.177±0.06 g/cm3(Predicted)
• PKA: 4.77±0.10(Predicted)
• CAS DataBase Reference: (5Z)-6A-CARBAPROSTAGLANDIN I2(CAS DataBase Reference)
• NIST Chemistry Reference: (5Z)-6A-CARBAPROSTAGLANDIN I2(69609-77-4)
• EPA Substance Registry System: (5Z)-6A-CARBAPROSTAGLANDIN I2(69609-77-4)

Safety Data

• Hazardous Substances Data: 69609-77-4(Hazardous Substances Data)

Usage

Description

(5Z)-6A-CARBAPROSTAGLANDIN I2, a synthetic analog of prostaglandin I2 (PGI2), is a significant compound in the regulation of inflammation and blood clotting. It possesses potent vasodilatory properties and acts as an inhibitor of platelet aggregation, making it a promising candidate for the treatment of various cardiovascular diseases.

Uses

Used in Pharmaceutical Industry:
(5Z)-6A-CARBAPROSTAGLANDIN I2 is used as a therapeutic agent for cardiovascular diseases such as hypertension and thrombosis. Its vasodilatory and platelet aggregation inhibition properties contribute to its effectiveness in managing these conditions.
Used in Anti-Inflammatory Applications:
(5Z)-6A-CARBAPROSTAGLANDIN I2 is used as an anti-inflammatory agent for conditions involving excessive inflammation, such as rheumatoid arthritis and inflammatory bowel disease. Its ability to regulate inflammation can provide relief and improve the quality of life for patients suffering from these conditions.
Used in Research and Development:
Due to its synthetic nature, (5Z)-6A-CARBAPROSTAGLANDIN I2 is used as a research tool for studying the pharmacokinetic and pharmacodynamic properties of prostaglandin analogs. This can lead to the development of improved therapeutic agents with better efficacy and fewer side effects.

Upstream product

• 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 
• 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-(2Z)-ylidene]-pentanoic acid methyl ester 
• 102491-13-4 (+)-(5Z)-9(O)-methanoprostacyclin methyl ester 11,15-diacetate 
• 71884-07-6 (5Z)-6α-carbaprostaglandin I₂ methyl ester 
• 41723-91-5 4-carboxybutyliden triphenylphosphorane sodium 
• 69552-54-1 3α-hydroxy-2β-<3α-hydroxy-1(E)-octenyl>bicyclo<3.3.0>octan-7-one 
• 70398-75-3 (3aα,6aα)-5β-(t-butyldimethylsilyloxy)-4α-<(E)-(3S*)-3-(t-butyldimethylsilyloxy)oct-1-enyl>perhydropentalen-2-one 
• 71967-39-0 (5Z)-15-dehydro-6α-carbaprostaglandin I₂ methyl ester 
• 82259-28-7 [(4S,5R)-4-Benzyloxymethyl-2-oxo-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-6a-yl]-trimethylsilanyl-acetic acid methyl ester 
• 73995-84-3 methyl 3α-hydroxy-2β-(benzyloxymethyl)-5ξ-(carbomethoxymethyl)cyclopentane-1ξ-acetate tetrahydropyran-2-yl ether 
• 73996-27-7 (5E and 5Z)-15-dehydro-6a-carbaprostaglandin I₂ methyl ester tetrahydropyranyl ether 
• 74042-66-3 5-[(3aS,4S,5R,6aS)-4-(1-Methoxy-1-methyl-ethoxymethyl)-5-(tetrahydro-pyran-2-yloxy)-hexahydro-pentalen-(2Z)-ylidene]-pentanoic acid 
• 74028-40-3 [(1R,2S,3R)-2-Benzyloxymethyl-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid methyl ester 

Downstream Products

• 69552-46-1 (5E)-carba-PGI2 
• 102491-28-1 (-)-ent-9(O)-methanoprostacyclin 

Relevant articles and documents

Facile synthesis of 6a-carbaprostaglandin I2

The optically active 6a-carbaprostaglandin I2 (2), a stable mimic of natural prostacyclin (1), was synthesized from the lactone 4 or the hydroxy acid 5, which were general synthetic intermediates for natural prostaglandins.

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.

A NEW SYNTHESIS OF (+)-6a-CARBAPROSTAGLANDIN I2 EMPLOYING YEAST REDUCTION OF A β-KETO ESTER DERIVED FROM cis-BICYCLOOCTANE-3,7-DIONE AS THE KEY-STEP

(+)-6a-carbaprostaglandin I2 (carbacyclin), a stable mimic of prostaglandin I2 (prostacyclin), was synthesized by utilizing the kinetic resolution of (+/-)-2-ethoxycarbonyl-7,7-ethylenedioxybicyclooctan-3-one in the course of its yeast reduction as