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prostaglandin F2α

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Origin: China

Cas No: 551-11-1

Specification: 99%min

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    CAS No.: 551-11-1 Formula: C20H34O5 Molecular Weight: 354.48100

    Description

    Prostaglandin F2α (PGF2α in prostanoid nomenclature), pharmaceutically termed dinoprost (INN), is a naturally occurring prostaglandin used in medicine to induce labor and as an abortifacient.
    In domestic mammals, it is produced by the uterus when stimulated by oxytocin, in the event that there has been no implantation during the follicular phase. It acts on the corpus luteum to cause luteolysis, forming a corpus albicans and stopping the production of progesterone. Action of PGF2α is dependent on the number of receptors on the corpus luteum membrane.
    The PGF2α isoform 8-iso-PGF2α was found in significantly increased amounts in patients with endometriosis, thus being a potential causative link in endometriosis-associated oxidative stress.

    Basic Info

    Chemical Name prostaglandin F2α
    Synonyms

    glandin;
    cyclosin;
    [3H]-PGF2alpha;
    (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-((S)-(E)-3-hydroxyoct-1-enyl)-cyclopentyl]hept-5-enoic acid;
    Dinprost;
    Prostaglandin F2α;
    Glandin N;
    enzaprost;
    panacelan;
    prostaglandin F2alpha;
    PGF2ALPHA;
    Prostaglandin F2a;
    DINOPROST;
    dinolytic;

    CAS No. 551-11-1
    Molecular Formula C20H34O5
    Molecular Weight 354.48100
    PSA 97.99000
    LogP 3.04290

    Properties

    Appearance & Physical State White to off-white crystalline solid.
    Density 1.153 g/cm3
    Boiling Point 531ºC at 760 mmHg
    Melting Point 25-35ºC
    Flash Point 289ºC
    Refractive Index 1.569
    Stability Stable for 2 yr in light resistant containers at 5-15ºC degrades in 1 wk when exposed to sunlight or in 3 mo at 40ºC stable in light, air, and heat.
    Storage Condition Store in a tightly closed container.

    Synthesis Route

    arachidonic acidprostaglandin D2+prostaglandin E2
    (3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol+4-carboxybutyl(triphenyl)phosphanium,bromideprostaglandin F2α
    Prostaglandin F2α methyl esterprostaglandin F2α

    Toxicity

    Exposure Route Type of Test Species Observed Dose/Duration Toxic Effects
    Intravenous TDLo - Lowest published toxic dose Human - woman 20 ug/kg 1.Gastrointestinal-hypermotility, diarrhea
    2.Gastrointestinal-nausea or vomiting
    Oral LD50 - Lethal dose, 50 percent kill Rodent - rat 1170 mg/kg 1.Lungs, Thorax, or Respiration-respiratory depression
    2.Gastrointestinal-hypermotility, diarrhea
    3.Nutritional and Gross Metabolic-body temperature decrease
    Subcutaneous LD50 - Lethal dose, 50 percent kill Rodent - rat 95 mg/kg 1.Details of toxic effects not reported other than lethal dose value

    Precursor

    (3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol
    (Z)-7-((1R,2R,3R,5S)-3-((tert-butyldimethylsilyl)oxy)-2-((S,E)-3-((tert-butyldimethylsilyl)oxy)oct-1-en-1-yl)-5-hydroxycyclopentyl)hept-5-enoic acid
    4-carboxybutyl(triphenyl)phosphanium,bromide
    Prostaglandin F2α methyl ester

    Downstream Product

    7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoctyl]cyclopentyl]heptanoic acid
    Prostaglandin F2α methyl ester
    9ALPHA, 11ALPHA, 15S-TRIHYDROXY-PROSTA-5Z, 13E-DIEN-1-OIC ACID, 1,9-LACTONE

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