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 prostacyclin (P839060), an eicosanoid that plays a crucial role in preventing the formation of platelet plugs and acts as an effective vasodilator. It serves as a useful marker of PGI2 biosynthesis in vivo, and when [3H]-PGI2 is injected into healthy human males, 6.6% of the radioactivity is recovered from urine as [3H]-6-keto PGF1α. 6-keto PGF1α is a prostaglandin Falpha with a keto substituent at the 6-position.

Uses

Used in Pharmaceutical Industry:
6-Keto-PGF1α is used as a biomarker for the assessment of prostacyclin (PGI2) biosynthesis in the human body. It helps in understanding the role of prostacyclin in various physiological processes and its potential involvement in certain diseases.
Used in Cardiovascular Research:
6-Keto-PGF1α is used as a research tool in cardiovascular studies to investigate the effects of prostacyclin on platelet aggregation and vasodilation. This can lead to the development of new therapeutic strategies for treating conditions related to blood clotting and vascular health.
Used in Diagnostic Applications:
6-Keto-PGF1α is used as a diagnostic marker to monitor the levels of prostacyclin in the body. This can be helpful in diagnosing and managing conditions where prostacyclin production is altered, such as certain types of vasculitis or thrombotic disorders.
Used in Drug Development:
6-Keto-PGF1α can be used in the development of new drugs targeting the prostacyclin pathway. Understanding the role of prostacyclin in various physiological processes can lead to the creation of novel therapeutic agents for treating a range of cardiovascular and other related conditions.

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

• 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 
• 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 
• 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 
• 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 
• 77192-49-5 prostacyclin*α-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.