71902-47-1

Basic information

• Product Name: 9ALPHA,15S-DIHYDROXY-11-OXO-PROSTA-5Z,13E,17Z-TRIEN-1-OIC ACID
• Synonyms: 9ALPHA,15S-DIHYDROXY-11-OXO-PROSTA-5Z,13E,17Z-TRIEN-1-OIC ACID;PROSTAGLANDIN D3;(Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(1E,3S,5Z)-3-hydroxyocta-1,5-dienyl]-3-oxocyclopentyl]hept-5-enoic acid;(5Z,13E,15S,17Z)-9α,15-Dihydroxy-11-oxoprosta-5,13,17-trien-1-oic acid;PGD3;Prostaglandin D3;Prostaglandin D3 Exclusive;ANOICLBSJIMQTA-WXGBOJPQSA-N
• CAS NO: 71902-47-1
• Molecular Formula: C20H30O5
• Molecular Weight: 350.45
• Mol File: 71902-47-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 561.2 °C at 760 mmHg
• Flash Point: 307.2 °C
• Appearance: /
• Density: 1.166 g/cm³
• Vapor Pressure: 6.25E-15mmHg at 25°C
• Refractive Index: 1.575
• CAS DataBase Reference: 9ALPHA,15S-DIHYDROXY-11-OXO-PROSTA-5Z,13E,17Z-TRIEN-1-OIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 9ALPHA,15S-DIHYDROXY-11-OXO-PROSTA-5Z,13E,17Z-TRIEN-1-OIC ACID(71902-47-1)
• EPA Substance Registry System: 9ALPHA,15S-DIHYDROXY-11-OXO-PROSTA-5Z,13E,17Z-TRIEN-1-OIC ACID(71902-47-1)

Safety Data

• Hazardous Substances Data: 71902-47-1(Hazardous Substances Data)

Usage

Description

9ALPHA,15S-DIHYDROXY-11-OXO-PROSTA-5Z,13E,17Z-TRIEN-1-OIC ACID, also known as Prostaglandin D3 (PGD3), is a member of the prostaglandin class D. It is a bioactive lipid derived from the metabolism of Eicosapentaenoic Acid (EPA) through the cyclooxygenase (COX) pathway. PGD3 is characterized by the presence of hydroxy groups at positions 9 and 15, and an oxo group at position 11, with the 5Z,13E,15S,17Z-stereoisomeric configuration. 9ALPHA,15S-DIHYDROXY-11-OXO-PROSTA-5Z,13E,17Z-TRIEN-1-OIC ACID plays a significant role in various physiological processes and has potential applications in the medical field.

Uses

Used in Pharmaceutical Industry:
9ALPHA,15S-DIHYDROXY-11-OXO-PROSTA-5Z,13E,17Z-TRIEN-1-OIC ACID is used as a bioactive compound for its potent effects on blood pressure and platelet aggregation. It is equipotent to PGD2 in decreasing systemic blood pressure in rats and intraocular pressure in rabbits, making it a valuable candidate for the development of drugs targeting these conditions.
Used in Cardiovascular Applications:
In the cardiovascular field, 9ALPHA,15S-DIHYDROXY-11-OXO-PROSTA-5Z,13E,17Z-TRIEN-1-OIC ACID is used as a therapeutic agent for its ability to lower blood pressure. This property makes it a potential candidate for the treatment of hypertension and related cardiovascular diseases.
Used in Ophthalmology:
9ALPHA,15S-DIHYDROXY-11-OXO-PROSTA-5Z,13E,17Z-TRIEN-1-OIC ACID is used as a therapeutic agent for its ability to decrease intraocular pressure. This application makes it a potential treatment option for glaucoma and other eye conditions related to increased intraocular pressure.
Used in Hematology:
In the field of hematology, 9ALPHA,15S-DIHYDROXY-11-OXO-PROSTA-5Z,13E,17Z-TRIEN-1-OIC ACID is used as an anti-platelet agent due to its potent inhibition of ADP-induced human platelet aggregation. This property makes it a potential candidate for the development of drugs targeting conditions related to blood clotting, such as thrombosis and atherosclerosis.
Overall, 9ALPHA,15S-DIHYDROXY-11-OXO-PROSTA-5Z,13E,17Z-TRIEN-1-OIC ACID, or Prostaglandin D3, is a versatile compound with potential applications in various medical fields, including cardiovascular, ophthalmology, and hematology, due to its unique properties and effects on blood pressure, intraocular pressure, and platelet aggregation.

InChI:InChI=1/C20H30O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h3-4,6-7,12-13,15-18,21-22H,2,5,8-11,14H2,1H3,(H,24,25)/b6-3-,7-4-,13-12+/t15-,16+,17+,18-/m0/s1

Upstream product

• 32233-42-4 (3aR,4R,5R,6aS)-4-((1E,5E)-(S)-3-Hydroxy-octa-1,5-dienyl)-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one 
• 75351-53-0 (3aR,4R,5R,6aS)-4-[(1E,5E)-(S)-3-(1-Methoxy-1-methyl-ethoxy)-octa-1,5-dienyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol 
• 75351-52-9 (3aR,4R,5R,6aS)-4-[(1E,5E)-(S)-3-(1-Methoxy-1-methyl-ethoxy)-octa-1,5-dienyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one 
• 75365-41-2 (E)-7-[(1R,2R,3R,5S)-5-Hydroxy-2-((1E,5E)-(S)-3-hydroxy-octa-1,5-dienyl)-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester 
• 75351-59-6 Benzoic acid (1R,2R,3R,4S)-4-hydroxy-2-((1E,5E)-(S)-3-hydroxy-octa-1,5-dienyl)-3-((E)-6-methoxycarbonyl-hex-2-enyl)-cyclopentyl ester 
• 75351-57-4 (E)-7-{(1R,2R,3R,5S)-3-Hydroxy-5-(2,2,2-trichloro-acetoxy)-2-[(1E,5E)-(S)-3-(2,2,2-trichloro-acetoxy)-octa-1,5-dienyl]-cyclopentyl}-hept-5-enoic acid methyl ester 
• 75351-56-3 (E)-7-{(1R,2R,3R,5S)-3-(Tetrahydro-pyran-2-yloxy)-5-(2,2,2-trichloro-acetoxy)-2-[(1E,5E)-(S)-3-(2,2,2-trichloro-acetoxy)-octa-1,5-dienyl]-cyclopentyl}-hept-5-enoic acid methyl ester 
• 75351-60-9 Benzoic acid (1R,2R,3R,4S)-3-((E)-6-methoxycarbonyl-hex-2-enyl)-4-(tetrahydro-pyran-2-yloxy)-2-[(1E,5E)-(S)-3-(tetrahydro-pyran-2-yloxy)-octa-1,5-dienyl]-cyclopentyl ester 
• 75351-58-5 Benzoic acid (1R,2R,3R,4S)-3-((E)-6-methoxycarbonyl-hex-2-enyl)-4-(2,2,2-trichloro-acetoxy)-2-[(1E,5E)-(S)-3-(2,2,2-trichloro-acetoxy)-octa-1,5-dienyl]-cyclopentyl ester 
• 32233-41-3 (3aR,4R,5R,6aS)-hexahydro-2-oxo-5-<(tetrahydro-2H-pyran-2-yl)oxy>-2H-cyclopentafuran-4-carboxaldehyde 

Relevant articles and documents

SYNTHESIS OF PROSTAGLANDIN D3

Prostaglandin D3 has been synthesized from (-)-2-oxa-3-oxo-6-syn-formyl-7-anti-(2-tetrahydropyranyloxy)-cis-bicyclooctane, a general synthetic intermediate for natural prostaglandins.