58962-34-8

Basic information

• Product Name: 6-KETO-PROSTAGLANDIN F1ALPHA
• Synonyms: PROSTAGLANDIN F1-ALPHA, 6-KETO-;6-KETO-PROSTAGLANDIN F1ALPHA;6-OXO-9ALPHA,11ALPHA,15S-TRIHYDROXY-PROST-13E-EN-1-OIC ACID;6-KETOPROSTAGLANDIN F1A;(9α,11α,13e,15s)-9,11,15-trihydroxy-6-oxoprosta-13-en-1-oic acid;7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]-6-oxoheptanoic acid;6-KETO-PROSTAGLANDIN F1ALPHA EIA STANDARD;6-Oxo-prostaglandin F1α, (9α,11α,13E,15S)-9,11,15-Trihydroxy-6-oxoprosta-13-en-1-oic acid
• CAS NO: 58962-34-8
• Molecular Formula: C₂₀H₃₄O₆
• Molecular Weight: 370.48
• Mol File: 58962-34-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 575.3 °C at 760 mmHg
• Flash Point: 315.8 °C
• Appearance: /
• Density: 1.191 g/cm³
• Vapor Pressure: 1.25E-15mmHg at 25°C
• Refractive Index: 1.561
• Storage Temp.: −20°C
• Solubility: ethanol: 10 mg/mL, clear, faintly yellow
• PKA: 4.69±0.10(Predicted)
• BRN: 2821925
• CAS DataBase Reference: 6-KETO-PROSTAGLANDIN F1ALPHA(CAS DataBase Reference)
• NIST Chemistry Reference: 6-KETO-PROSTAGLANDIN F1ALPHA(58962-34-8)
• EPA Substance Registry System: 6-KETO-PROSTAGLANDIN F1ALPHA(58962-34-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: UK8428300
• F: 8-10
• Hazardous Substances Data: 58962-34-8(Hazardous Substances Data)

Usage

Description

6-keto prostaglandin F1α (6-keto PGF1α) is the inactive, non-enzymatic hydrolysis product of PGI2. 6-keto PGF1α serves as a useful marker of PGI2 biosynthesis in vivo. When [3H]-PGI2 is injected into healthy human males, 6.6% of the radioactivity is recovered from urine as [3H]-6-keto PGF1α.

Uses

6-Ketoprostaglandin F1α is the stable hydrolysis product of prostacyclin (P839060), an eicosanoid which prevents the formation of platelet plugs and an effective vasodilator.

Definition

ChEBI: A prostaglandin Falpha that is prostaglandin F1alpha bearing a keto substituent at the 6-position.

InChI:InChI=1/C20H34O6/c1-2-3-4-7-14(21)10-11-16-17(19(24)13-18(16)23)12-15(22)8-5-6-9-20(25)26/h10-11,14,16-19,21,23-24H,2-9,12-13H2,1H3,(H,25,26)/b11-10+/t14?,16-,17-,18-,19+/m1/s1

Upstream product

• 77192-49-5 prostacyclin*α-cyclodextrin 
• 79672-82-5 methyl 7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((S,E)-3-(tert-butyldimethylsilyloxy)oct-1-enyl)-5-hydroxycyclopentyl)-6-oxoheptanoate 
• 92052-44-3 7-{(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-hydroxy-cyclopentyl}-6-nitro-heptanoic acid methyl ester 
• 92052-44-3 7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-hydroxy-cyclopentyl}-6-nitro-heptanoic acid methyl ester 
• 112329-44-9 7-{(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-hydroxy-cyclopentyl}-6,6-dimethoxy-heptanoic acid methyl ester 
• 112329-43-8 7-Hydroxy-6-nitro-heptanoic acid methyl ester 
• 13154-40-0 6-nitrohexanoic acid methyl ester 
• 92077-99-1 11,15-O-Bis(tert-butyldimethylsilyl)-6-nitro-PGE₁ methyl ester 
• 88462-11-7 Methyl 6-nitro-6-heptenoate 
• 14273-90-6 methyl 6-bromohexanoate 
• 77192-53-1 prostacyclin*γ-cyclodextrin 
• 77164-53-5 prostacyclin*β-cyclodextrin 
• 63557-55-1 6-keto-PGF_1α methyl ester 
• 35121-78-9 Epoprostenol 

Downstream Products

• 63557-55-1 6-keto-PGF_1α methyl ester 

Relevant articles and documents

Nitro-Olefin Trapping Reactions of Enolates In Situ Generated by Conjugate Addition Reaction: Short Syntheses of PGE1, 6-Oxo-PGE1, 6-Oxo-PGF1α, and PGI2

The nitro-olefin trapping of the enolates in situ generated by conjugate addition of organocopper reagents to the chiral oxygenated cyclopentenone synthon, R-4, gives the three-component coupling products in a regiospecific manner.The intermediary nitronate anion 17 is further transformed into the nitro compound or 6-oxo-PGE1 (19) in a single pot.This coupling reaction is applicable to syntheses of naturally occurring prostaglandins such as PGE1, 6-oxo-PGF1α, and PGI2.

Short synthesis of 6-oxoprostaglandin E1 and 6-oxoprostaglandin F(1α)

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The synthesis of 2,3-dinorprostacyclin metabolites - A new approach to spirolactone hemiacetals

The major human urinary metabolites of prostacyclin and 6-keto-PGF1α have been synthesized by a direct route, involving three-carbon homologation of bicyclic lactone intermediates and spontaneous spirolactonization of the products. The fact that these 2,3-dinor-6-oxo metabolites exist almost exclusively as spirolactone hemiacetals under acidic conditions (pH 5 and below) may explain the reported difficulties in derivatizing samples of biological origin. Several 19,19.20,20-d4 metabolites have also been synthesized.