Product Name

  • Name

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

  • EINECS 200-164-5
  • CAS No. 53-16-7
  • Article Data173
  • CAS DataBase
  • Density 1.164 g/cm3
  • Solubility water: 0.03 g/L
  • Melting Point 258-261 ºC
  • Formula C18H22O2
  • Boiling Point 445.2 ºC at 760 mmHg
  • Molecular Weight 270.371
  • Flash Point 189.7 ºC
  • Transport Information
  • Appearance crystalline solid
  • Safety 53-45
  • Risk Codes 45-60-61
  • Molecular Structure Molecular Structure of 53-16-7 (1,3,5(10)-Estratrien-3-ol-17-one)
  • Hazard Symbols ToxicT
  • Synonyms delta-1,3,5-estratrien-3-beta-ol-17-one;Hormestrin;Oestrin;delta-1,3,5-oestratrien-3-beta-ol-17-one;Estrona [Spanish];CMC_13458;Ovifollin;Wynestron;component of Mal-O-Fem;Cristallovar;Menagen;Estrusol;hydroxyestrones;Ketohydroxyoestrin;.delta.-1,3, 5-Oestratrien-3.beta.-ol-17-one;Folipex;3-Hydroxy-17-keto-estra-1,3,5-triene;Disynformon;3-Hydroxy-oestra-1,3, 5(10)-trien-17-one;Estrone-A;Destrone;Ovex (tablets);Estrol;Follicunodis;
  • PSA 37.30000
  • LogP 3.81740

Synthetic route

estradiol
50-28-2

estradiol

Estrone
53-16-7

Estrone

Conditions
ConditionsYield
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%
R-estradiol
493001-46-0

R-estradiol

tert-butyl alcohol
75-65-0

tert-butyl alcohol

Estrone
53-16-7

Estrone

Conditions
ConditionsYield
100%
estrone acetate
901-93-9

estrone acetate

Estrone
53-16-7

Estrone

Conditions
ConditionsYield
With methanol; zinc98%
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
92803-51-5

17-oxo-1,3,5(10)-estratrien-3-yl 2-(trimethylsilyl)ethyl butanedioate

Estrone
53-16-7

Estrone

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 27℃; for 24h;97%
10β-hydroxy-19-norandrost-4-ene-3,17-dione
5189-96-8

10β-hydroxy-19-norandrost-4-ene-3,17-dione

Estrone
53-16-7

Estrone

Conditions
ConditionsYield
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
1422954-71-9

C23H34O3Si

Estrone
53-16-7

Estrone

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 2h;95%
estrone 3-methyl ether
1624-62-0

estrone 3-methyl ether

Estrone
53-16-7

Estrone

Conditions
ConditionsYield
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
95282-98-7

19-acetoxyandrosta-1,4-diene-3,17-dione

Estrone
53-16-7

Estrone

Conditions
ConditionsYield
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%
(polystyrene resin Novabiochem)-C6H4(C6H5)2CNHSO2O-3-estrone

(polystyrene resin Novabiochem)-C6H4(C6H5)2CNHSO2O-3-estrone

Estrone
53-16-7

Estrone

Conditions
ConditionsYield
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
90850-47-8

3-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>estra-1,3,5(10)-trien-17-one

Estrone
53-16-7

Estrone

Conditions
ConditionsYield
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
194094-44-5

19-tert-butyldimethylsilyloxy-androsta-1,4-diene-3,17-dione

Estrone
53-16-7

Estrone

Conditions
ConditionsYield
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
84882-46-2

4β,5-epoxy-5β-androstane-3,17,19-trione

A

Estrone
53-16-7

Estrone

B

4β,5-dihydroxy-5α-androstane-3,17,19-trione 4,19-hemiacetal
84882-49-5

4β,5-dihydroxy-5α-androstane-3,17,19-trione 4,19-hemiacetal

Conditions
ConditionsYield
With perchloric acid In tetrahydrofuran; water for 72h;A 3%
B 82%
(8R,9S,13S,14S)-13-Methyl-3-[1-(2-trimethylsilanyl-ethoxy)-ethoxy]-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one

(8R,9S,13S,14S)-13-Methyl-3-[1-(2-trimethylsilanyl-ethoxy)-ethoxy]-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one

Estrone
53-16-7

Estrone

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 45℃; for 20h;82%
estradiol
50-28-2

estradiol

ethylene glycol
107-21-1

ethylene glycol

A

Estrone
53-16-7

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
900-83-4

(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
ConditionsYield
With dimethyl sulfoxide; [ReOCl3(PPh3)2] In toluene for 5h; Heating;A 18%
B 82%
3-benzyloxyestra-1,3,5(10)-trien-17-one
858-98-0

3-benzyloxyestra-1,3,5(10)-trien-17-one

Estrone
53-16-7

Estrone

Conditions
ConditionsYield
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
124522-65-2

2α-acetoxy-19-oxoandrost-4-ene-3,17-dione

Estrone
53-16-7

Estrone

Conditions
ConditionsYield
With potassium hydrogencarbonate In methanol; water for 2h; Ambient temperature; further reagents;80%
3,17-dioxo-4β,5-epoxy-5β-androstan-19-oic acid
76251-10-0

3,17-dioxo-4β,5-epoxy-5β-androstan-19-oic acid

A

Estrone
53-16-7

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
76251-11-1, 76251-12-2

(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
ConditionsYield
In decalin for 2.5h; Heating;A 9%
B 79%
3β-Hydroxy-19-norandrosta-1(10),5-dien-17-one
843-81-2

3β-Hydroxy-19-norandrosta-1(10),5-dien-17-one

Estrone
53-16-7

Estrone

Conditions
ConditionsYield
With 1-Methyl-4-piperidone; aluminum isopropoxide In toluene for 4h; Heating;77%
Androsta-1,4-diene-3,17-dione
897-06-3

Androsta-1,4-diene-3,17-dione

Estrone
53-16-7

Estrone

Conditions
ConditionsYield
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
60788-62-7

2,4-dibromo-3-hydroxy-13β-estra-1,3,5(10)-trien-17-one

A

Estrone
53-16-7

Estrone

B

4-bromo-3-hydroxyestra-1,3,5(10)-trien-17-one
1630-82-6

4-bromo-3-hydroxyestra-1,3,5(10)-trien-17-one

Conditions
ConditionsYield
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
58534-72-8

estrone-3′-hemisuccinate

Estrone
53-16-7

Estrone

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 27℃; for 32h;66%
(3aS,3bR,9bS,11aS)‐11a‐methyl‐7‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)‐1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH‐cyclopenta[a]phenanthren‐1‐one

(3aS,3bR,9bS,11aS)‐11a‐methyl‐7‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)‐1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH‐cyclopenta[a]phenanthren‐1‐one

Estrone
53-16-7

Estrone

Conditions
ConditionsYield
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
76920-48-4

17-oxo-estra-1,3,5(10)-trien-3-yl Se-phenyl selenocarbonate

A

Estrone
53-16-7

Estrone

B

estrone formate

estrone formate

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In xylene at 144℃;A 62%
B 18%
estradiol
145164-84-7

estradiol

Estrone
53-16-7

Estrone

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methyl-phenol; aluminum isopropoxide; benzaldehyde In 2-methyltetrahydrofuran at 20℃; for 4h; Oppenauer Oxidation; Inert atmosphere;58%
C20H26O3

C20H26O3

A

Estrone
53-16-7

Estrone

B

3-Hydroxy-9β-estra-1,3,5(10)-trien-17-one
1225-03-2

3-Hydroxy-9β-estra-1,3,5(10)-trien-17-one

Conditions
ConditionsYield
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
843-81-2

3β-Hydroxy-19-norandrosta-1(10),5-dien-17-one

A

Estrone
53-16-7

Estrone

B

17-Oxo-19-norandrost-1(10),5-dien-3β-yl trifluoroacetate
116202-05-2

17-Oxo-19-norandrost-1(10),5-dien-3β-yl trifluoroacetate

Conditions
ConditionsYield
With triethylamine In dichloromethane; dimethyl sulfoxide at -78℃;A 53%
B 20%
3β-Hydroxy-19-norandrosta-1(10),5-dien-17-one
843-81-2

3β-Hydroxy-19-norandrosta-1(10),5-dien-17-one

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

A

Estrone
53-16-7

Estrone

B

17-Oxo-19-norandrost-1(10),5-dien-3β-yl trifluoroacetate
116202-05-2

17-Oxo-19-norandrost-1(10),5-dien-3β-yl trifluoroacetate

Conditions
ConditionsYield
With triethylamine In dichloromethane; dimethyl sulfoxide at -78℃;A 53%
B 20%
C18H24O3

C18H24O3

A

Estrone
53-16-7

Estrone

B

10β-hydroxy-19-norandrost-4-ene-3,17-dione
5189-96-8

10β-hydroxy-19-norandrost-4-ene-3,17-dione

Conditions
ConditionsYield
With acetic acid for 1.33333h; Heating;A 18%
B 50%
4β,5-epoxy-5β-androstane-3,17,19-trione
84882-46-2

4β,5-epoxy-5β-androstane-3,17,19-trione

A

Estrone
53-16-7

Estrone

B

A-nor-5β-androstane-3,17,19-trione

A-nor-5β-androstane-3,17,19-trione

C

4β,5-dihydroxy-5α-androstane-3,17,19-trione 4,19-hemiacetal
84882-49-5

4β,5-dihydroxy-5α-androstane-3,17,19-trione 4,19-hemiacetal

D

4-hydroxyandrost-4-ene-3,17,19-trione

4-hydroxyandrost-4-ene-3,17,19-trione

Conditions
ConditionsYield
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%
Estrone
53-16-7

Estrone

3-hydroxy-estra-1,3,5(10)-trien-17-one oxime
5982-51-4

3-hydroxy-estra-1,3,5(10)-trien-17-one oxime

Conditions
ConditionsYield
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; ethanol99%
Estrone
53-16-7

Estrone

17β-hydrazoestra-1,3,5(10)-trien-3-ol
7628-02-6

17β-hydrazoestra-1,3,5(10)-trien-3-ol

Conditions
ConditionsYield
With triethylamine; hydrazine In ethanol; water100%
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
53-16-7

Estrone

pivaloyl chloride
3282-30-2

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
4003-22-9

(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
ConditionsYield
With triethylamine In chloroform100%
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
110-87-2

3,4-dihydro-2H-pyran

Estrone
53-16-7

Estrone

3-tetrahydropyranyloxy-1,3,5(10)-estratrien-17-one
7103-48-2

3-tetrahydropyranyloxy-1,3,5(10)-estratrien-17-one

Conditions
ConditionsYield
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%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

Estrone
53-16-7

Estrone

estrone triflate
92817-04-4

estrone triflate

Conditions
ConditionsYield
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
53-16-7

Estrone

ethylene glycol
107-21-1

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
900-83-4

(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
ConditionsYield
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
53-16-7

Estrone

methanesulfonyl chloride
124-63-0

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
3381-23-5

(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
ConditionsYield
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
53-16-7

Estrone

D-camphor-10-sulfonyl chloride
21286-54-4, 39262-22-1

D-camphor-10-sulfonyl chloride

estrone-3-((+)-10-camphor)sulfonate

estrone-3-((+)-10-camphor)sulfonate

Conditions
ConditionsYield
With pyridine Ambient temperature;100%
Estrone
53-16-7

Estrone

aminooxyacetic acid
645-88-5

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
16218-61-4

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
ConditionsYield
With pyridine at 20℃; for 17h;100%
triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

Estrone
53-16-7

Estrone

(8R,9S,13S,14S)-13-Methyl-3-triisopropylsilanyloxy-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one

(8R,9S,13S,14S)-13-Methyl-3-triisopropylsilanyloxy-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide Inert atmosphere;100%
Estrone
53-16-7

Estrone

ethylene dibromide
106-93-4

ethylene dibromide

3-(2’-bromoethoxy)estra-1,3,5(10)-trien-17-one
191155-58-5

3-(2’-bromoethoxy)estra-1,3,5(10)-trien-17-one

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water Reflux;100%
With sodium hydroxide In tetrahydrofuran; water Reflux;84%
Estrone
53-16-7

Estrone

benzoyl chloride
98-88-4

benzoyl chloride

estrone 3-benzoate
2393-53-5

estrone 3-benzoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20 - 30℃;100%
With pyridine at 25℃;95%
With pyridine for 2h; Inert atmosphere;94%
Methyl 4-(bromomethyl)benzoate
2417-72-3

Methyl 4-(bromomethyl)benzoate

Estrone
53-16-7

Estrone

methyl 4-((((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)oxy)methyl)benzoate

methyl 4-((((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)oxy)methyl)benzoate

Conditions
ConditionsYield
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%
Br(CH2)2OCH3

Br(CH2)2OCH3

Estrone
53-16-7

Estrone

3-(2'-Methoxyethoxy)-1,3,5(10)-estratrien-17-one
243638-26-8

3-(2'-Methoxyethoxy)-1,3,5(10)-estratrien-17-one

Conditions
ConditionsYield
With caesium carbonate In acetonitrile99.4%
trifluoromethane sulfonyl chloride
421-83-0

trifluoromethane sulfonyl chloride

Estrone
53-16-7

Estrone

estrone triflate
92817-04-4

estrone triflate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 0.25h; Inert atmosphere;99%
With triethylamine91%
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;82%
Estrone
53-16-7

Estrone

16,16-di-deuterium-estra-1,3,5(10)-triene-17-one
56588-58-0

16,16-di-deuterium-estra-1,3,5(10)-triene-17-one

Conditions
ConditionsYield
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
Estrone
53-16-7

Estrone

ethane-1,2-dithiol
540-63-6

ethane-1,2-dithiol

C20H26OS2
14485-61-1

C20H26OS2

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene Heating;99%
With toluene-4-sulfonic acid In toluene Reflux;
Estrone
53-16-7

Estrone

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

3-(O-tert-butyl(dimethyl)silyl)estrone
57711-40-7

3-(O-tert-butyl(dimethyl)silyl)estrone

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1h;99%
With 1H-imidazole99%
With 1H-imidazole In DMF (N,N-dimethyl-formamide) at 20℃;98%
Estrone
53-16-7

Estrone

methyl iodide
74-88-4

methyl iodide

estrone 3-methyl ether
1624-62-0

estrone 3-methyl ether

Conditions
ConditionsYield
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%
Estrone
53-16-7

Estrone

benzyl bromide
100-39-0

benzyl bromide

3-benzyloxyestra-1,3,5(10)-trien-17-one
858-98-0

3-benzyloxyestra-1,3,5(10)-trien-17-one

Conditions
ConditionsYield
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
53-16-7

Estrone

(aminooxy)acetic acid hemihydrochloride
2921-14-4, 7776-18-3, 20295-82-3

(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
16218-61-4

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
ConditionsYield
With pyridine at 23℃; for 16h;99%
Isopropenyl acetate
108-22-5

Isopropenyl acetate

Estrone
53-16-7

Estrone

estrone acetate
901-93-9

estrone acetate

Conditions
ConditionsYield
With iron(III) trifluoromethanesulfonate at 20℃; for 5h; Schlenk technique;99%
With iodine at 85 - 90℃; for 0.0833333h;96%
With iodine at 90℃;
1H-imidazole
288-32-4

1H-imidazole

Estrone
53-16-7

Estrone

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

3-tert-butyldimethylsilyloxy-estra-1,3,5(10)-triene-17-one

3-tert-butyldimethylsilyloxy-estra-1,3,5(10)-triene-17-one

Conditions
ConditionsYield
In N,N-dimethyl-formamide99%
In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide94%
1H-imidazole
288-32-4

1H-imidazole

Estrone
53-16-7

Estrone

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

A

3-tert-butyldimethylsilyloxy-estra-1,3,5(10)-triene-17-one

3-tert-butyldimethylsilyloxy-estra-1,3,5(10)-triene-17-one

B

[17(20)E]-Carbethoxymethylideneestra-1,3,5(10)-trieno-[3,2,e]-1',2',3'-oxathiazine-2,2'-dioxide

[17(20)E]-Carbethoxymethylideneestra-1,3,5(10)-trieno-[3,2,e]-1',2',3'-oxathiazine-2,2'-dioxide

Conditions
ConditionsYield
In N,N-dimethyl-formamideA 99%
B n/a
Estrone
53-16-7

Estrone

C18H19(2)H3O2
1021878-04-5

C18H19(2)H3O2

Conditions
ConditionsYield
With hydrogen; water-d2; palladium on activated charcoal at 20℃; for 72h;99%
Estrone
53-16-7

Estrone

di-tert-butylchlorosilane
56310-18-0

di-tert-butylchlorosilane

C26H40O3Si
1315577-32-2

C26H40O3Si

Conditions
ConditionsYield
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%
Estrone
53-16-7

Estrone

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

estrone 3-methyl ether
1624-62-0

estrone 3-methyl ether

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 16h;99%

Estrone Chemical Properties

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 Uses

 Estrone (CAS NO.53-16-7) is mainly used as a metabolite of 17-Estradiol.

Estrone Consensus Reports

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.

Estrone Safety Profile

Hazard Codes of Estrone (CAS NO.53-16-7): ToxicT
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.

Estrone Specification

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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