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1,3,5(10)-Estratrien-3-ol-17-one

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1,3,5(10)-Estratrien-3-ol-17-one Basic information
1,3,5(10)-Estratrien-3-ol-17-one Chemical Properties
  • Melting point:258-260 °C(lit.)
  • Boiling point:353.48°C (rough estimate)
  • alpha 158 º (c=1, dioxane)
  • Density 1.2360
  • refractive index 165 ° (C=1, Dioxane)
  • Flash point:9℃
  • storage temp. Refrigerator
  • form Crystalline Powder or Crystals
  • pkapKa 10.77±0.02(H2O)(Approximate)
  • color White to almost white
  • Water Solubility 0.03 g/L
  • Merck 3708
  • BRN 1915077
  • InChIKeyDNXHEGUUPJUMQT-CBZIJGRNSA-N
  • CAS DataBase Reference53-16-7(CAS DataBase Reference)
  • NIST Chemistry Reference3-Hydroxyestra-1,3,5(10)-trien-17-one(53-16-7)
  • EPA Substance Registry SystemEstrone (53-16-7)
Safety Information
MSDS
1,3,5(10)-Estratrien-3-ol-17-one Usage And Synthesis
  • Chemical PropertiesCrystalline Solid
  • Chemical PropertiesEstrone is an odorless white crystalline powder.
  • OriginatorEstrone,Abbott
  • UsesEstrone is a metabolite of 17β-Estradiol (E888000). During the metabolism, it is in rapid equilibrium with Estriol (E888960) and 17β-Estradiol (E888000) (1). Causes the feminization of male fish at human and animal waste sites (2). This compound is a contaminant of emerging concern (CECs). Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants.
  • UsesA metabolite of 17β-Estradiol.
  • Usesestrogen
  • DefinitionChEBI: A 17-oxo steroid that is estra-1,3,5(10)-triene substituted by an hydroxy group at position 3 and an oxo group at position 17.
  • Manufacturing Process1-Vinyl-1,2,3,4-tetrahydronaphthalene-1,6-diol reacts with 2- methylcyclopentane-1,3-dione in the presence of Triton B in tert-butanol gives a good yield of δ1,3,5(10),9(11)-8,14-secoestratetraen-3-ol-14,17-dione, melting point 124°-126°C (from methanol).
    δ1,3,5(10),9(11)-8,14-Secoestratetraen-3-ol-14,17-dione under influence of hydrochloric acid in tetrahydrofurane cyclises into δ1,3,5(10),8,14-estrapentaen- 3-ol-17-one, melting point 216°-218°C.
    δ1,3,5(10),8,14-Estrapentaen-3-ol-17-one is converted to d,l-8-dehydroestrone by selective hydrogenation with hydrogen, melting point 251°-254°C (from methanol). Exhaustive hydrogenation of δ1,3,5(10),8,14-estrapentaen-3-ol-17- one give d,l-8-isoestrone.
    d,l-8-Isoestrone in the presence of hydrochloric acid in tetrahydrofurane isomerizes into d,l-9(11)-dehydroestrone, melting point 262°-265°C (from alcohol).
    Hydrogenation of d,l-9(11)-dehydroestrone in tetrahydrofuran in the presence of Pd/CaCO3 yields the estrone, melting point 251°-252°C (from acetone).
  • brand nameEstrogenic Substance (Wyeth); Theelin (Parkdale).
  • Therapeutic FunctionEstrogen
  • General DescriptionEstrone, 3-hydroxyestra-1,3,5(10)-trien-17-one, is less active than estradiol but more active than itsmetabolite, estriol. As the salt of its 3-sulfate ester, estroneis the primary ingredient in conjugated estrogens, USP, andesterified estrogens, USP. Although originally obtainedfrom the urine of pregnant mares (about 10 mg/L), estroneis now prepared synthetically. Estrone itself is not availablein commercial oral formulations, but can be obtained at compounding pharmacies as a topical formulation. Oleoylestrone,the C3 ester of estrone with oleic acid, is in phase IIclinical trials for the treatment of obesity. This acyl estronederivative reduces fat stores by a mechanism not involvingthe ER, although some of the oleoyl-estrone is hydrolyzedto estrone in vivo.
  • HazardA carcinogen (OSHA).
  • Safety ProfileConfirmed carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic, and teratogenic data. A poison by intraperitoneal and subcutaneous routes. Human reproductive effects by implantation: spermatogenesis and impotence. Mutation data reported. A steroid drug for the treatment of menopause and ovariectomy symptoms. When heated to decomposition it emits acrid smoke and irritating fumes.
  • Chemical SynthesisEstrone, 3-hydroxyestra-1,3,5(10)-trien-17-one (28.1.9), has been made synthetically in various ways. According to one of the first and most simple schemes, synthesis was carried out in the following manner. Condensation of 3-methoxyphenylacetylene with bicyclohexane-1,5-dione in a Favorskii reaction conditions lead to the corresponding carbinol (28.1.1). The triple bond was reduced by hydrogen over a palladium catalyst, forming the tertiary alcohol (28.1.2), which was then dehydrated in acidic conditions to give the compound (28.1.3). Intramolecular alkylation of this compound in the presence of anhydrous aluminum chloride formed a tetracyclic ketone (28.1.4), which during condensation with benzaldehyde was transformed into an eneone (28.1.5). This was methylated at the β-position relative to the keto-group by methyl iodide in the presence of potassium tert-butylate, and the resulting compound (28.1.6) underwent ozonolysis, forming the dicarboxylic acid (28.1.7). Cyclization of this compound to a cyclopentanone derivative lead to the formation of methyl ester of the desired estrone (28.1.8), and demethylation of the phenolic hydroxyl group by hydrobromic acid formed the desired estrone (28.1.9).

  • Potential ExposureSynthesized from ergosterol. Used in combination with progestogen as an oral contraceptive.
  • ShippingUN3249 Medicine, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
  • Purification MethodsPurify estrone by chromatography on silica gel, eluting with 2:1 hexane/EtOAc and recrystallising from EtOH or Et2O/EtOH. [Danishefsky & Cain J Am Chem Soc 98 4975 1976.] The acetate [901-93-9] crystallises from EtOH with m 125-127o. [Beilstein 8 III 1171.]
  • IncompatibilitiesMay react exothermically with reducing agents to generate flammable gaseous hydrogen. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, and epoxides.
1,3,5(10)-Estratrien-3-ol-17-one Preparation Products And Raw materials
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