Product Name

  • Name

    Estetrol

  • EINECS
  • CAS No. 15183-37-6
  • Article Data8
  • CAS DataBase
  • Density 1.343 g/cm3
  • Solubility
  • Melting Point 233-236°C
  • Formula C18H24O4
  • Boiling Point 491.9 °C at 760 mmHg
  • Molecular Weight 304.386
  • Flash Point 231.7 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 15183-37-6 (Estetrol)
  • Hazard Symbols
  • Synonyms Estra-1,3,5(10)-triene-3,15,16,17-tetrol, (15α,16α,17β)-;15a-Hydroxyestriol;(15α,16α,17β)-estra-1,3,5(10)-triene-3,15,16,17-tetrol;(8R,9S,13S,14S,15R,16R,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,15,16,17-tetrol;
  • PSA 80.92000
  • LogP 1.55080

Synthetic route

(15α,16α,17β)-3-hydroxyestra-1,3,5(10)-triene-15,16,17-triyl triacetate

(15α,16α,17β)-3-hydroxyestra-1,3,5(10)-triene-15,16,17-triyl triacetate

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
With potassium carbonate In methanol at 20 - 25℃; for 3h; Inert atmosphere;97.22%
With potassium carbonate at 25℃; for 4h;13 g
(15α,16α,17β)-3-hydroxyestra-1,3,5(10)-triene-15,16,17-triyl triformiate

(15α,16α,17β)-3-hydroxyestra-1,3,5(10)-triene-15,16,17-triyl triformiate

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
With potassium carbonate In methanol at 20 - 25℃; for 3h; Inert atmosphere;97%
15α,16α-dihydroxyestradiol 3-benzoate

15α,16α-dihydroxyestradiol 3-benzoate

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
With sodium hydroxide In methanol at 40 - 45℃; for 2h;94%
17-acetyl estetrol

17-acetyl estetrol

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
With potassium carbonate In methanol at 20℃; for 4h;92.5%
Stage #1: 17-acetyl estetrol With methanol; potassium carbonate at 20℃; for 4h;
Stage #2: With hydrogenchloride In chloroform; water		92.5%
3-benzoyloxy-17β-(1-butoxyethoxy)estra-1,3,5(10),15-tetraene

3-benzoyloxy-17β-(1-butoxyethoxy)estra-1,3,5(10),15-tetraene

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Stage #1: 3-benzoyloxy-17β-(1-butoxyethoxy)estra-1,3,5(10),15-tetraene With trimethylamine-N-oxide In tetrahydrofuran at 50 - 55℃;
Stage #2: With potassium carbonate In tetrahydrofuran; water		91.7%
Multi-step reaction with 2 steps
1: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
2: sodium hydroxide / methanol / 2 h / 40 - 45 °C
View Scheme
3,17β-O-bis(tetrahydro-2H-pyran-2-yl)-Δ-15-estradiol

3,17β-O-bis(tetrahydro-2H-pyran-2-yl)-Δ-15-estradiol

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Stage #1: 3,17β-O-bis(tetrahydro-2H-pyran-2-yl)-Δ-15-estradiol With 4-methylmorpholine N-oxide In tetrahydrofuran at 20℃;
Stage #2: With toluene-4-sulfonic acid at 40℃; pH=4;		40%
3,17β-diacetoxyestra-1,3,5(10)-triene-15α,16α-diol
16127-99-4

3,17β-diacetoxyestra-1,3,5(10)-triene-15α,16α-diol

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
With sodium hydroxide In methanol at 4℃; for 24h;21 mg
15-dehydroestradiol 3,17-diacetate
16127-98-3

15-dehydroestradiol 3,17-diacetate

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 46 percent / OsO4 / benzene; pyridine / Ambient temperature
2: 21 mg / 1 N NaOH / methanol / 24 h / 4 °C
View Scheme
Reaxys ID: 11888347

Reaxys ID: 11888347

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Estrone
53-16-7

Estrone

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: potassium carbonate / dichloromethane; methanol / 16 h / Reflux
2.1: triethylamine / dichloromethane / 1 h / 20 °C
3.1: oxygen / palladium diacetate / dichloromethane; dimethyl sulfoxide / 35 °C
4.1: cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 1 h / 20 °C
4.2: 2 h / 0 - 8 °C
5.1: pyridine / dmap / 2 h / 20 °C
6.1: trimethylamine-N-oxide / ~5percent w/w OsO4 on PVP / tetrahydrofuran / 50 °C
7.1: hydrogen / palladium 10% on activated carbon / methanol / 24 h / 20 °C / 760.05 Torr
8.1: potassium carbonate; methanol / 4 h / 20 °C
View Scheme
Multi-step reaction with 10 steps
1: triethylamine / dichloromethane / 20 - 30 °C
2: orthoformic acid triethyl ester; toluene-4-sulfonic acid / 15 h / 35 °C
3: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
4: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
5: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
6: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
7: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
8: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
9: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
10: sodium hydroxide / methanol / 2 h / 40 - 45 °C
View Scheme
Multi-step reaction with 8 steps
1.1: triethylamine / dichloromethane / 20 - 30 °C
2.1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / 15 h / 35 °C
3.1: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
4.1: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
5.1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
6.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
7.1: toluene-4-sulfonic acid / dichloromethane / 5 - 20 °C / Inert atmosphere; Molecular sieve
8.1: 4-methylmorpholine N-oxide / tetrahydrofuran / 20 °C
8.2: 40 °C / pH 4
View Scheme
(14α)-3-benzyloxy-1,3,5(10),15-estratetraen-17-one
138743-03-0

(14α)-3-benzyloxy-1,3,5(10),15-estratetraen-17-one

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 1 h / 20 °C
1.2: 2 h / 0 - 8 °C
2.1: pyridine / dmap / 2 h / 20 °C
3.1: trimethylamine-N-oxide / ~5percent w/w OsO4 on PVP / tetrahydrofuran / 50 °C
4.1: hydrogen / palladium 10% on activated carbon / methanol / 24 h / 20 °C / 760.05 Torr
5.1: potassium carbonate; methanol / 4 h / 20 °C
View Scheme
(17β)-3-(phenylmethoxy)-estra-1,3,5(10),15-tetraen-17-ol

(17β)-3-(phenylmethoxy)-estra-1,3,5(10),15-tetraen-17-ol

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / dmap / 2 h / 20 °C
2: trimethylamine-N-oxide / ~5percent w/w OsO4 on PVP / tetrahydrofuran / 50 °C
3: hydrogen / palladium 10% on activated carbon / methanol / 24 h / 20 °C / 760.05 Torr
4: potassium carbonate; methanol / 4 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; tert-butyl alcohol; water / 24 h / 20 - 25 °C / Inert atmosphere
2: acetic anhydride; pyridine / 1.42 h / 0 - 10 °C
3: palladium 10% on activated carbon; hydrogen / ethyl acetate / 4 h / 20 - 25 °C / 760.05 Torr
4: potassium carbonate / methanol / 3 h / 20 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; tert-butyl alcohol; water / 24 h / 20 - 25 °C / Inert atmosphere
2: triethylamine; dmap / dichloromethane / 2 h / Inert atmosphere
3: palladium 10% on activated carbon; hydrogen / ethyl acetate / 3 h / 20 - 25 °C / 760.05 Torr
4: potassium carbonate / methanol / 3 h / 20 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1: osmium(VIII) oxide; trimethylamine-N-oxide / tetrahydrofuran / 16 h / 50 °C / Inert atmosphere
2: dmap / pyridine / 4 h / 25 °C
3: palladium 10% on activated carbon; hydrogen / methanol / 22 h / 45 °C / 2250.23 Torr
4: potassium carbonate / 4 h / 25 °C
View Scheme
17β-acetyloxy-3-benzyloxy-estra-1,3,5(10),15-tetraene

17β-acetyloxy-3-benzyloxy-estra-1,3,5(10),15-tetraene

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: trimethylamine-N-oxide / ~5percent w/w OsO4 on PVP / tetrahydrofuran / 50 °C
2: hydrogen / palladium 10% on activated carbon / methanol / 24 h / 20 °C / 760.05 Torr
3: potassium carbonate; methanol / 4 h / 20 °C
View Scheme
3-benzyloxyestra-1,3,5(10)-trien-17-one
858-98-0

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

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: triethylamine / dichloromethane / 1 h / 20 °C
2.1: oxygen / palladium diacetate / dichloromethane; dimethyl sulfoxide / 35 °C
3.1: cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 1 h / 20 °C
3.2: 2 h / 0 - 8 °C
4.1: pyridine / dmap / 2 h / 20 °C
5.1: trimethylamine-N-oxide / ~5percent w/w OsO4 on PVP / tetrahydrofuran / 50 °C
6.1: hydrogen / palladium 10% on activated carbon / methanol / 24 h / 20 °C / 760.05 Torr
7.1: potassium carbonate; methanol / 4 h / 20 °C
View Scheme
3-benzyloxy-17-trimethylsilyloxy-estra-1,3,5(10),16-tetraene
213819-19-3

3-benzyloxy-17-trimethylsilyloxy-estra-1,3,5(10),16-tetraene

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: oxygen / palladium diacetate / dichloromethane; dimethyl sulfoxide / 35 °C
2.1: cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 1 h / 20 °C
2.2: 2 h / 0 - 8 °C
3.1: pyridine / dmap / 2 h / 20 °C
4.1: trimethylamine-N-oxide / ~5percent w/w OsO4 on PVP / tetrahydrofuran / 50 °C
5.1: hydrogen / palladium 10% on activated carbon / methanol / 24 h / 20 °C / 760.05 Torr
6.1: potassium carbonate; methanol / 4 h / 20 °C
View Scheme
3,17β-O-bis(methoxymethyl)-Δ-15-estradiol

3,17β-O-bis(methoxymethyl)-Δ-15-estradiol

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Stage #1: 3,17β-O-bis(methoxymethyl)-Δ-15-estradiol With trimethylamine-N-oxide In tetrahydrofuran at 50 - 55℃;
Stage #2: With acetic acid In tetrahydrofuran; water Reagent/catalyst;		0.26 g
estrone 3-benzoate
2393-53-5

estrone 3-benzoate

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / 15 h / 35 °C
2.1: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
3.1: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
4.1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
5.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
6.1: toluene-4-sulfonic acid / dichloromethane / 5 - 20 °C / Inert atmosphere; Molecular sieve
7.1: 4-methylmorpholine N-oxide / tetrahydrofuran / 20 °C
7.2: 40 °C / pH 4
View Scheme
Multi-step reaction with 7 steps
1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / 15 h / 35 °C
2: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
3: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
4: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
5: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
6: toluene-4-sulfonic acid; lithium bromide / tetrahydrofuran / 20 °C / Inert atmosphere
7: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 7 steps
1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / 15 h / 35 °C
2: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
3: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
4: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
5: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
6: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
7: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 8 steps
1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / 15 h / 35 °C
2: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
3: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
4: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
5: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
6: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
7: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
8: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 9 steps
1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / 15 h / 35 °C
2: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
3: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
4: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
5: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
6: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
7: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
8: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
9: sodium hydroxide / methanol / 2 h / 40 - 45 °C
View Scheme
17,17-ethylenedioxyestrone 3-benzoate

17,17-ethylenedioxyestrone 3-benzoate

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
2.1: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
3.1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
4.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
5.1: toluene-4-sulfonic acid / dichloromethane / 5 - 20 °C / Inert atmosphere; Molecular sieve
6.1: 4-methylmorpholine N-oxide / tetrahydrofuran / 20 °C
6.2: 40 °C / pH 4
View Scheme
Multi-step reaction with 6 steps
1: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
2: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
3: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
4: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
5: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
6: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 6 steps
1: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
2: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
3: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
4: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
5: toluene-4-sulfonic acid; lithium bromide / tetrahydrofuran / 20 °C / Inert atmosphere
6: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 7 steps
1: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
2: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
3: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
4: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
5: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
6: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
7: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 8 steps
1: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
2: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
3: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
4: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
5: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
6: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
7: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
8: sodium hydroxide / methanol / 2 h / 40 - 45 °C
View Scheme
3-benzoyloxy-16-bromo-17,17-(ethylenedioxy)estra-1,3,5(10)-triene

3-benzoyloxy-16-bromo-17,17-(ethylenedioxy)estra-1,3,5(10)-triene

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
2.1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
3.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
4.1: toluene-4-sulfonic acid / dichloromethane / 5 - 20 °C / Inert atmosphere; Molecular sieve
5.1: 4-methylmorpholine N-oxide / tetrahydrofuran / 20 °C
5.2: 40 °C / pH 4
View Scheme
Multi-step reaction with 5 steps
1: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
2: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
3: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
4: toluene-4-sulfonic acid; lithium bromide / tetrahydrofuran / 20 °C / Inert atmosphere
5: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 5 steps
1: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
2: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
3: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
4: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
5: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 6 steps
1: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
2: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
3: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
4: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
5: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
6: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 7 steps
1: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
2: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
3: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
4: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
5: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
6: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
7: sodium hydroxide / methanol / 2 h / 40 - 45 °C
View Scheme
17,17-ethylenedioxy-3-hydroxyestra-1,3,5(10),15-tetraene

17,17-ethylenedioxy-3-hydroxyestra-1,3,5(10),15-tetraene

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
2: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
3: toluene-4-sulfonic acid; lithium bromide / tetrahydrofuran / 20 °C / Inert atmosphere
4: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 4 steps
1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
2: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
4: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 5 steps
1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
2: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
3: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
4: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
5: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 6 steps
1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
2: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
3: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
4: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
5: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
6: sodium hydroxide / methanol / 2 h / 40 - 45 °C
View Scheme
Multi-step reaction with 4 steps
1.1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
2.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
3.1: toluene-4-sulfonic acid / dichloromethane / 5 - 20 °C / Inert atmosphere; Molecular sieve
4.1: 4-methylmorpholine N-oxide / tetrahydrofuran / 20 °C
4.2: 40 °C / pH 4
View Scheme
3-hydroxyestra-1,3,5(10),15-tetraen-17-one
3563-25-5

3-hydroxyestra-1,3,5(10),15-tetraen-17-one

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
3: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 3 steps
1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
2: toluene-4-sulfonic acid; lithium bromide / tetrahydrofuran / 20 °C / Inert atmosphere
3: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 4 steps
1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
2: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
3: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
4: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 5 steps
1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
2: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
3: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
4: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
5: sodium hydroxide / methanol / 2 h / 40 - 45 °C
View Scheme
Multi-step reaction with 3 steps
1.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
2.1: toluene-4-sulfonic acid / dichloromethane / 5 - 20 °C / Inert atmosphere; Molecular sieve
3.1: 4-methylmorpholine N-oxide / tetrahydrofuran / 20 °C
3.2: 40 °C / pH 4
View Scheme
Δ-15-estradiol 3-benzoate

Δ-15-estradiol 3-benzoate

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
2: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 3 steps
1: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
2: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
3: sodium hydroxide / methanol / 2 h / 40 - 45 °C
View Scheme
estra-1,3,5(10),15-tetraene-3,17β-diol
58699-14-2

estra-1,3,5(10),15-tetraene-3,17β-diol

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene-4-sulfonic acid; lithium bromide / tetrahydrofuran / 20 °C / Inert atmosphere
2: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
2: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
2: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
3: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 4 steps
1: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
2: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
3: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
4: sodium hydroxide / methanol / 2 h / 40 - 45 °C
View Scheme
Multi-step reaction with 2 steps
1.1: toluene-4-sulfonic acid / dichloromethane / 5 - 20 °C / Inert atmosphere; Molecular sieve
2.1: 4-methylmorpholine N-oxide / tetrahydrofuran / 20 °C
2.2: 40 °C / pH 4
View Scheme
(17β)-3-(phenylmethoxy)-estra-1,3,5(10)-triene-15,16,17-triol

(17β)-3-(phenylmethoxy)-estra-1,3,5(10)-triene-15,16,17-triol

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine; dmap / ethyl acetate / 3 h / 35 - 40 °C / Inert atmosphere
2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 3 h / 20 - 25 °C / 760.05 Torr
3: potassium carbonate / methanol / 3 h / 20 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: dmap / pyridine / 4 h / 25 °C
2: palladium 10% on activated carbon; hydrogen / methanol / 22 h / 45 °C / 2250.23 Torr
3: potassium carbonate / 4 h / 25 °C
View Scheme
(15α,16α,17β)-3-(benzyloxy)estra-1,3,5(10)-triene-15,16,17-triyl triacetate

(15α,16α,17β)-3-(benzyloxy)estra-1,3,5(10)-triene-15,16,17-triyl triacetate

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 3 h / 20 - 25 °C / 760.05 Torr
2: potassium carbonate / methanol / 3 h / 20 - 25 °C / Inert atmosphere
View Scheme
(15α,16α,17β)-3-(benzyloxy)estra-1,3,5(10)-triene-15,16,17-triol

(15α,16α,17β)-3-(benzyloxy)estra-1,3,5(10)-triene-15,16,17-triol

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine; dmap / dichloromethane / 2 h / Inert atmosphere
2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 3 h / 20 - 25 °C / 760.05 Torr
3: potassium carbonate / methanol / 3 h / 20 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: acetic anhydride; pyridine / 1.42 h / 0 - 10 °C
2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 4 h / 20 - 25 °C / 760.05 Torr
3: potassium carbonate / methanol / 3 h / 20 - 25 °C / Inert atmosphere
View Scheme
4-bromoethylbutanoate
2969-81-5

4-bromoethylbutanoate

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

4-O-[15α,16α,17β-trihydroxyestra-1,3,5(10)-trien-3-yl]butanoic acid ethyl ester

4-O-[15α,16α,17β-trihydroxyestra-1,3,5(10)-trien-3-yl]butanoic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 80℃; for 1h; Alkylation;206 mg
15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

4-O-[15α,16α,17β-trihydroxyestra-1,3,5(10)-trien-3-yl]butanoic acid

4-O-[15α,16α,17β-trihydroxyestra-1,3,5(10)-trien-3-yl]butanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 206 mg / K2CO3 / dimethylsulfoxide / 1 h / 80 °C
2: 151 mg / 5 N aq. NaOH / methanol / 14 h / 4 °C
View Scheme

Estetrol Specification

The Estetrol, with the CAS registry number 15183-37-6, is also known as (15α,16α,17β)-estra-1,3,5(10)-triene-3,15,16,17-tetrol. It belongs to the product categories of Intermediates & Fine Chemicals; Pharmaceuticals; Steroids. This chemical's molecular formula is C18H24O4 and molecular weight is 304.38. What's more, its IUPAC name is (8R,9S,13S,14S,15R,16R,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,15,16,17-tetrol. It is used as a metabolite of estradiol. It is an estrogenic steroid synthesized exclusively by the fetal liver during human pregnancy and reaching the maternal circulation through the placenta.

Physical properties of Estetrol are: (1)ACD/LogP: 2.21; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.21; (4)ACD/LogD (pH 7.4): 2.21; (5)ACD/BCF (pH 5.5): 27.95; (6)ACD/BCF (pH 7.4): 27.91; (7)ACD/KOC (pH 5.5): 377.55; (8)ACD/KOC (pH 7.4): 377.02; (9)#H bond acceptors: 4; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 36.92 Å2; (13)Index of Refraction: 1.65; (14)Molar Refractivity: 82.68 cm3; (15)Molar Volume: 226.6 cm3; (16)Polarizability: 32.77×10-24cm3; (17)Surface Tension: 59.3 dyne/cm; (18)Density: 1.343 g/cm3; (19)Flash Point: 231.7 °C; (20)Enthalpy of Vaporization: 79.91 kJ/mol; (21)Boiling Point: 491.9 °C at 760 mmHg; (22)Vapour Pressure: 1.71E-10 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC12CCC3C(C1C(C(C2O)O)O)CCC4=C3C=CC(=C4)O
(2)Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1[C@H]([C@H]([C@@H]2O)O)O)CCC4=C3C=CC(=C4)O
(3)InChI: InChI=1S/C18H24O4/c1-18-7-6-12-11-5-3-10(19)8-9(11)2-4-13(12)14(18)15(20)16(21)17(18)22/h3,5,8,12-17,19-22H,2,4,6-7H2,1H3/t12-,13-,14-,15-,16-,17+,18+/m1/s1
(4)InChIKey: AJIPIJNNOJSSQC-NYLIRDPKSA-N

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