Conditions | Yield |
---|---|
With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O) In tert-butyl alcohol at 130℃; for 20h; | 100% |
With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O) In tert-butyl alcohol for 20h; Reflux; | 100% |
With polystyrene-supported(cathecholato) oxoRe cat. act by iPrOH; dimethyl sulfoxide In toluene for 4h; Heating; Dean-Stark apparatus; | 98% |
Conditions | Yield |
---|---|
100% |
Conditions | Yield |
---|---|
With methanol; zinc | 98% |
With tetrabutyl ammonium fluoride In tetrahydrofuran at 27℃; for 72h; | 94% |
With lipase from Candida cylindracea; octanol In various solvent(s) at 37℃; for 144h; | 90% |
With sodium hydroxide In methanol; water for 0.25h; |
17-oxo-1,3,5(10)-estratrien-3-yl 2-(trimethylsilyl)ethyl butanedioate
Estrone
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 27℃; for 24h; | 97% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In diethyl ether Ambient temperature; | 96% |
With toluene-4-sulfonic acid In diethyl ether Ambient temperature; Yield given; | |
With acetic acid In chloroform-d1 |
C23H34O3Si
Estrone
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 2h; | 95% |
Conditions | Yield |
---|---|
With aluminium trichloride; sodium iodide In dichloromethane; acetonitrile for 5.5h; Heating; | 93% |
Stage #1: estrone 3-methyl ether With aluminum (III) chloride; sodium iodide In dichloromethane at 0 - 20℃; Inert atmosphere; Stage #2: With hydrogenchloride; water In dichloromethane Inert atmosphere; | 92% |
With boron tribromide at -30 - 0℃; for 2.5h; | 88% |
19-acetoxyandrosta-1,4-diene-3,17-dione
Estrone
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 20℃; for 0.05h; | 90% |
With sodium hydroxide In methanol at 20℃; for 2h; | 76% |
With potassium hydroxide In methanol at 20℃; for 2h; | 50.1% |
Estrone
Conditions | Yield |
---|---|
With diethylamine In ethanol; dichloromethane at 55 - 60℃; for 8h; Hydrolysis; | 90% |
3-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>estra-1,3,5(10)-trien-17-one
Estrone
Conditions | Yield |
---|---|
With sodium methylate In N,N-dimethyl-formamide at 20℃; for 2h; Product distribution; regeneration reactions of the parent compound from different perfluoroaryl derivatives to the alcohols; other educts and products, different times, temperatures and mol ratios of the educts; | 87% |
19-tert-butyldimethylsilyloxy-androsta-1,4-diene-3,17-dione
Estrone
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h; | 85.9% |
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h; |
4β,5-epoxy-5β-androstane-3,17,19-trione
A
Estrone
B
4β,5-dihydroxy-5α-androstane-3,17,19-trione 4,19-hemiacetal
Conditions | Yield |
---|---|
With perchloric acid In tetrahydrofuran; water for 72h; | A 3% B 82% |
Estrone
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 45℃; for 20h; | 82% |
estradiol
ethylene glycol
A
Estrone
B
(8R,9S,13S,14S)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-17,2′-[1,3]dioxolan]-3-ol
Conditions | Yield |
---|---|
With dimethyl sulfoxide; [ReOCl3(PPh3)2] In toluene for 5h; Heating; | A 18% B 82% |
Conditions | Yield |
---|---|
With 5%-palladium/activated carbon; hydrogen In tetrahydrofuran; methanol at 40℃; for 12h; | 81% |
With palladium on activated charcoal; hydrogen In methanol at 40℃; for 12h; | 81% |
2α-acetoxy-19-oxoandrost-4-ene-3,17-dione
Estrone
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In methanol; water for 2h; Ambient temperature; further reagents; | 80% |
3,17-dioxo-4β,5-epoxy-5β-androstan-19-oic acid
A
Estrone
B
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-2,3,6,7,8,9,11,12,13,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-4,17-dione
Conditions | Yield |
---|---|
In decalin for 2.5h; Heating; | A 9% B 79% |
Conditions | Yield |
---|---|
With 1-Methyl-4-piperidone; aluminum isopropoxide In toluene for 4h; Heating; | 77% |
Conditions | Yield |
---|---|
With iodine; triethylphosphine In toluene at 120℃; for 10h; Concentration; Solvent; Reagent/catalyst; Temperature; | 72% |
With mineral oil at 530℃; in ein mit Glasperlen beschicktes Rohr; | |
at 325℃; unter vermindertem Druck; | |
at 325℃; |
2,4-dibromo-3-hydroxy-13β-estra-1,3,5(10)-trien-17-one
A
Estrone
B
4-bromo-3-hydroxyestra-1,3,5(10)-trien-17-one
Conditions | Yield |
---|---|
With formic acid; palladium on activated charcoal In N,N-dimethyl-formamide for 1.75h; Heating; | A 20% B 70% |
With formic acid; palladium on activated charcoal In N,N-dimethyl-formamide for 1.75h; Heating; variation in time and temperature; | A 20% B 70% |
With hydrogen; palladium on activated charcoal In ethanol Ambient temperature; Yield given; |
estrone-3′-hemisuccinate
Estrone
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 27℃; for 32h; | 66% |
Estrone
Conditions | Yield |
---|---|
With [Rh2(bpy)2(μ-OAc)2(OAc)2]; oxygen; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide under 760.051 Torr; for 24h; Irradiation; | 63% |
17-oxo-estra-1,3,5(10)-trien-3-yl Se-phenyl selenocarbonate
A
Estrone
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In xylene at 144℃; | A 62% B 18% |
estradiol
Estrone
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-4-methyl-phenol; aluminum isopropoxide; benzaldehyde In 2-methyltetrahydrofuran at 20℃; for 4h; Oppenauer Oxidation; Inert atmosphere; | 58% |
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water at 20 - 25℃; for 0.5h; Inert atmosphere; | A 56% B 32% |
3β-Hydroxy-19-norandrosta-1(10),5-dien-17-one
A
Estrone
B
17-Oxo-19-norandrost-1(10),5-dien-3β-yl trifluoroacetate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane; dimethyl sulfoxide at -78℃; | A 53% B 20% |
3β-Hydroxy-19-norandrosta-1(10),5-dien-17-one
trifluoroacetic anhydride
A
Estrone
B
17-Oxo-19-norandrost-1(10),5-dien-3β-yl trifluoroacetate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane; dimethyl sulfoxide at -78℃; | A 53% B 20% |
Conditions | Yield |
---|---|
With acetic acid for 1.33333h; Heating; | A 18% B 50% |
4β,5-epoxy-5β-androstane-3,17,19-trione
A
Estrone
C
4β,5-dihydroxy-5α-androstane-3,17,19-trione 4,19-hemiacetal
Conditions | Yield |
---|---|
With perchloric acid In tetrahydrofuran for 24h; | A 8% B 7% C 17% D 49% |
With perchloric acid In tetrahydrofuran for 24h; Product distribution; reaction in the presence of H2SO4; acid- and base-catalysed reactions of 4β,5β- and 4α,5α-epoxyandrostane-3,17,19-triones; | A 8% B 7% C 17% D 49% |
Conditions | Yield |
---|---|
With pyridine; hydroxylamine hydrochloride In ethanol; water for 6h; Reflux; Inert atmosphere; | 100% |
With pyridine; hydroxylamine hydrochloride In ethanol for 6h; Reflux; | 100% |
With hydroxylamine hydrochloride In pyridine; ethanol | 99% |
Conditions | Yield |
---|---|
With triethylamine; hydrazine In ethanol; water | 100% |
With triethylamine; hydrazine In ethanol for 3h; Reflux; | 96% |
With hydrazine hydrate In ethanol at 45℃; for 2h; | 95% |
With hydrazine | |
With hydrazine In butan-1-ol; diethylene glycol for 1h; Reflux; |
Estrone
pivaloyl chloride
(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl pivalate
Conditions | Yield |
---|---|
With triethylamine In chloroform | 100% |
With dmap; triethylamine In dichloromethane at 0℃; for 0.3h; Inert atmosphere; | 96% |
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; Sealed tube; | 87% |
3,4-dihydro-2H-pyran
Estrone
3-tetrahydropyranyloxy-1,3,5(10)-estratrien-17-one
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane at 23℃; for 18h; | 100% |
With pyridinium p-toluenesulfonate In dichloromethane at 21℃; for 20h; | 100% |
With pyridinium p-toluenesulfonate In dichloromethane at 23℃; for 18h; | 100% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere; | 100% |
With pyridine In dichloromethane at 0 - 20℃; for 1.5h; Inert atmosphere; | 100% |
With triethylamine In dichloromethane at 0℃; for 1h; | 99% |
Estrone
ethylene glycol
(8R,9S,13S,14S)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-17,2′-[1,3]dioxolan]-3-ol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene Heating; | 100% |
With trimethyl orthoformate In toluene; acetonitrile at 20℃; | 99% |
With toluene-4-sulfonic acid In benzene for 13h; Heating; | 94% |
Estrone
methanesulfonyl chloride
(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl methanesulfonate
Conditions | Yield |
---|---|
With pyridine Ambient temperature; | 100% |
In dichloromethane Heating; | 92% |
With triethylamine In dichloromethane for 3h; | 91% |
With triethylamine In dichloromethane 0 deg C to r.t., 24 h; | 88% |
With pyridine at 0 - 25℃; |
Estrone
D-camphor-10-sulfonyl chloride
Conditions | Yield |
---|---|
With pyridine Ambient temperature; | 100% |
Estrone
aminooxyacetic acid
2-({(E)-[(8R,9S,13S,14S)-3-hydroxy-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-ylidene]amino}oxy)acetic acid
Conditions | Yield |
---|---|
With pyridine at 20℃; for 17h; | 100% |
triisopropylsilyl chloride
Estrone
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide Inert atmosphere; | 100% |
Estrone
ethylene dibromide
3-(2’-bromoethoxy)estra-1,3,5(10)-trien-17-one
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran; water Reflux; | 100% |
With sodium hydroxide In tetrahydrofuran; water Reflux; | 84% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20 - 30℃; | 100% |
With pyridine at 25℃; | 95% |
With pyridine for 2h; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetone for 48h; Schlenk technique; Inert atmosphere; Reflux; | 100% |
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetone for 48h; Schlenk technique; Inert atmosphere; Reflux; | 100% |
Estrone
3-(2'-Methoxyethoxy)-1,3,5(10)-estratrien-17-one
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile | 99.4% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 0.25h; Inert atmosphere; | 99% |
With triethylamine | 91% |
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere; | 82% |
Estrone
16,16-di-deuterium-estra-1,3,5(10)-triene-17-one
Conditions | Yield |
---|---|
With [D]-sodium hydroxide In deuteromethanol; water-d2 for 24h; Reflux; Inert atmosphere; | 99% |
With deuteriated sodium hydroxide In deuteromethanol; water-d2 at 60℃; for 24h; | |
With deuteromethanol; sodium methylate |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene Heating; | 99% |
With toluene-4-sulfonic acid In toluene Reflux; |
Estrone
tert-butyldimethylsilyl chloride
3-(O-tert-butyl(dimethyl)silyl)estrone
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1h; | 99% |
With 1H-imidazole | 99% |
With 1H-imidazole In DMF (N,N-dimethyl-formamide) at 20℃; | 98% |
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; sodium hydroxide In dichloromethane at 70℃; for 3h; | 99% |
With potassium carbonate In N,N-dimethyl-formamide Heating; | 98% |
With potassium carbonate In N,N-dimethyl-formamide 1) reflux, 2 h, 2) r.t., 5 d; | 97% |
Conditions | Yield |
---|---|
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane for 24h; Heating; | 99% |
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane for 24h; Heating; | 99% |
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water for 24h; Heating / reflux; | 99% |
Estrone
(aminooxy)acetic acid hemihydrochloride
2-({(E)-[(8R,9S,13S,14S)-3-hydroxy-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-ylidene]amino}oxy)acetic acid
Conditions | Yield |
---|---|
With pyridine at 23℃; for 16h; | 99% |
Conditions | Yield |
---|---|
With iron(III) trifluoromethanesulfonate at 20℃; for 5h; Schlenk technique; | 99% |
With iodine at 85 - 90℃; for 0.0833333h; | 96% |
With iodine at 90℃; |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide | 99% |
In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide | 94% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide | A 99% B n/a |
Estrone
C18H19(2)H3O2
Conditions | Yield |
---|---|
With hydrogen; water-d2; palladium on activated charcoal at 20℃; for 72h; | 99% |
Conditions | Yield |
---|---|
Stage #1: Estrone; di-tert-butylchlorosilane With 1H-imidazole In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: With N-Bromosuccinimide In dichloromethane Stage #3: With water; sodium hydroxide In dichloromethane; N,N-dimethyl-formamide at 20℃; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 16h; | 99% |
Molecular Structure of Estrone (CAS NO.53-16-7):
Molecular Formula: C18H22O2
Molecular Weight: 270.3661
IUPAC Name: (8R,9S,13S,14S)-3-Hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
CAS NO: 53-16-7
EINECS: 200-164-5
Classification Code: Drug / Therapeutic Agent ; Estrogen ; Estrogens ; Hormone ; Hormones ; Hormones, Hormone Substitutes, and Hormone Antagonists ; Human Data ; Mutation data ; Natural Product ; Reproductive Effect ; Tumor data
Melting point: 258-260 °C
Index of Refraction: 1.587
Molar Refractivity: 78.04 cm3
Molar Volume: 232.1 cm3
Surface Tension: 46 dyne/cm
Density: 1.164 g/cm3
Flash Point: 189.7 °C
Enthalpy of Vaporization: 73.02 kJ/mol
Boiling Point: 445.2 °C at 760 mmHg
Vapour Pressure: 1.54E-08 mmHg at 25 °C
alpha :158 °(c=1, dioxane)
refractive index: 165 °(C=1, Dioxane)
Water Solubility: 0.03 g/L
Product Categories: Steroids; Various Metabolites and Impurities; 17-Ketosteroids; Biochemistry; Hydroxyketosteroids; Metabolites & Impurities
Estrone (CAS NO.53-16-7) is mainly used as a metabolite of 17-Estradiol.
NTP 10th Report on Carcinogens. Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 6 , 1974,p. 123.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: )IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 21 , 1979,p. 343.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory.
Hazard Codes of Estrone (CAS NO.53-16-7): T
Risk Statements: 45-60-61
R45: May cause cancer.
R60: May impair fertility.
R61: May cause harm to the unborn child.
Safety Statements: 53-45
S53: Avoid exposure - obtain special instructions before use.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
WGK Germany: 3
RTECS: KG8575000
Confirmed 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.
Synonyms of Estrone (CAS NO.53-16-7) are1,3,5(10)-Estratrien-3-ol-17-one ; 1,3,5(10)-Oestratrien-3-ol-17-one ; 3-08-00-01171 (Beilstein Handbook Reference) ; 3-Hydroxy-17-keto-estra-1,3,5-triene ; 3-Hydroxy-17-keto-oestra-1,3,5-triene ; 3-Hydroxy-oestra-1,3,5(10)-trien-17-one ; 3-Hydroxyestra-1,3,5(10)-trien-17-one ; 3-Hydroxyestra-1,3,5(10)-triene-17-one ; Aquacrine ; Crinovaryl ; Cristallovar ; Crystogen ; Destrone ; Disynformon ; E(sub 1) ; Endofolliculina ; Estra-1,3,5(10)-trien-17-one, 3-hydroxy- ; Estrogenic substance ; Estron ; Estrona ; Estrone-A ; Estronum ; Estrovarin ; Estrugenone ; Estrusol ; Fem-O-Gen ; Femestrone injection ; Femidyn ; Folikrin ; Folipex ; Folisan ; Follestrine ; Follestrol ; Follicular hormone ; Folliculin ; Folliculine ; Folliculine benzoate ; Follicunodis ; Glandubolin ; Hiestrone ; Hormestrin ; Hormofollin ; Hormovarine ; Kestrone ; Ketodestrin ; Ketohydroxy-estratriene ; Ketohydroxyestrin ; Ketohydroxyoestrin ; Kolpon ; Menagen ; Menformon ; Mestronaq ; Natural estrogenic substance-estrone ; Oestrin ; Oestroform ; Oestrone ; Oestronum ; Oestroperos ; Ovex (tablets) ; Ovifollin ; Perlatan ; Solliculin ; Theelin ; Thelestrin ; Thelykinin ; Thynestron ; Tokokin ; Unden ; Unden (pharmaceutical) ; Wynestron ; delta-1,3,5-Estratrien 3beta-ol-17-one ; delta-1,3,5-Oestratrien-3beta-ol-17-one ; delta-1,3,5-estratrien-3-beta-ol-17-one ; delta-1,3,5-oestratrien-3-beta-ol-17-one .
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