Product Name

  • Name

    19-Norethindrone acetate

  • EINECS 200-132-0
  • CAS No. 51-98-9
  • Article Data25
  • CAS DataBase
  • Density 1.14 g/cm3
  • Solubility 3.162mg/L(10 oC)
  • Melting Point 161-162°
  • Formula C22H28O3
  • Boiling Point 454.7 °C at 760 mmHg
  • Molecular Weight 340.463
  • Flash Point 197.1 °C
  • Transport Information
  • Appearance
  • Safety 36/37
  • Risk Codes 40-48
  • Molecular Structure Molecular Structure of 51-98-9 (19-Norethindrone acetate)
  • Hazard Symbols HarmfulXn
  • Synonyms 19-Nor-17a-pregn-4-en-20-yn-3-one,17-hydroxy-, acetate (6CI,8CI);17-Acetoxy-19-nor-17a-pregn-4-en-20-yn-3-one;17a-Ethinyl-19-nortestosteroneacetate;17a-Ethinyl-4-estrene-17b-ol-acetate-3-one;17b-Acetoxy-17a-ethinyl-4-estren-3-one;17b-Hydroxy-19-nor-17a-pregn-4-en-20-yn-3-one acetate;19-Norethynyltestosterone acetate;Aygestin;Estalis;Gynovlane;Milli-Anovlar;Milligynon;Miniphase;NSC 22844;Norethindrone 17-acetate;Norethindrone acetate;Norethynyltestosteroneacetate;Norlutate;Norlutin acetate;Orlutate;Primolut-Nor;19-Norpregn-4-en-20-yn-3-one,17-(acetyloxy)-, (17a)-;
  • PSA 43.37000
  • LogP 4.06330

Synthetic route

norethisterone
68-22-4

norethisterone

acetic acid
64-19-7

acetic acid

norethisterone acetate
51-98-9

norethisterone acetate

Conditions
ConditionsYield
With sodium carbonate; trifluoroacetic anhydride In benzene for 0.5h; Ambient temperature;96.5%
Stage #1: acetic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In chloroform at 20℃; for 0.5h; Inert atmosphere;
Stage #2: norethisterone With dmap In chloroform for 18h; Inert atmosphere; Reflux;
93%
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃;91.6%
In trifluoroacetic acid90%
With benzenesulfonyl chloride In pyridine for 48h;79%
norethisterone
68-22-4

norethisterone

acetyl chloride
75-36-5

acetyl chloride

norethisterone acetate
51-98-9

norethisterone acetate

Conditions
ConditionsYield
With pyridine; dmap In 1,2-dichloro-ethane at 0℃;92%
norethisterone
68-22-4

norethisterone

acetic anhydride
108-24-7

acetic anhydride

norethisterone acetate
51-98-9

norethisterone acetate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 50℃;91%
scandium tris(trifluoromethanesulfonate) In acetonitrile86%
With dmap In toluene at 80 - 90℃; for 3h;28 g
3,17-diacetoxy-19-nor-17βH-pregna-3,5-dien-20-yne
2205-78-9

3,17-diacetoxy-19-nor-17βH-pregna-3,5-dien-20-yne

norethisterone acetate
51-98-9

norethisterone acetate

Conditions
ConditionsYield
With tetrahydrofuran; potassium hydroxide
With hydrogenchloride
norethisterone
68-22-4

norethisterone

norethisterone acetate
51-98-9

norethisterone acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: methanol.KOH; THF
View Scheme
Multi-step reaction with 2 steps
1: acetic anhydride; toluene-4-sulfonic acid
2: tetrahydrofuran; methanol
View Scheme
methanolic potassium hydroxide

methanolic potassium hydroxide

ether-light petroleum ether

ether-light petroleum ether

3,17-diacetoxy-19-nor-17βH-pregna-3,5-dien-20-yne
2205-78-9

3,17-diacetoxy-19-nor-17βH-pregna-3,5-dien-20-yne

norethisterone acetate
51-98-9

norethisterone acetate

Conditions
ConditionsYield
In tetrahydrofuran; methanol
In tetrahydrofuran; methanol
octanol
111-87-5

octanol

norethisterone acetate
51-98-9

norethisterone acetate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: ammonium chloride; lithium / tetrahydrofuran; ethanol; ammonia; water
2: aluminum isopropoxide; sodium sulfate / methanol; water; cyclohexanone; toluene
3: 1,4-dioxane; methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ISOPROPYLAMIDE
4: hydrogenchloride / methanol; water
5: acetic anhydride; toluene-4-sulfonic acid
6: tetrahydrofuran; methanol
View Scheme
3-methoxy-17-hydroxyestra-2,5(10)-diene
1091-93-6

3-methoxy-17-hydroxyestra-2,5(10)-diene

norethisterone acetate
51-98-9

norethisterone acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: aluminum isopropoxide; sodium sulfate / methanol; water; cyclohexanone; toluene
2: 1,4-dioxane; methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ISOPROPYLAMIDE
3: hydrogenchloride / methanol; water
4: acetic anhydride; toluene-4-sulfonic acid
5: tetrahydrofuran; methanol
View Scheme
3-methoxyestra-2,5(10)-dien-17-one
17976-32-8

3-methoxyestra-2,5(10)-dien-17-one

norethisterone acetate
51-98-9

norethisterone acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1,4-dioxane; methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ISOPROPYLAMIDE
2: hydrogenchloride / methanol; water
3: acetic anhydride; toluene-4-sulfonic acid
4: tetrahydrofuran; methanol
View Scheme
3-methoxy-19-nor-17βH-pregna-2,5(10)-dien-20-yn-17-ol
19357-36-9

3-methoxy-19-nor-17βH-pregna-2,5(10)-dien-20-yn-17-ol

norethisterone acetate
51-98-9

norethisterone acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / methanol; water
2: acetic anhydride; toluene-4-sulfonic acid
3: tetrahydrofuran; methanol
View Scheme
3-ethoxy-17α-ethynyl-19-desmethylpregna-3,5-diene-17β-ol
96487-85-3

3-ethoxy-17α-ethynyl-19-desmethylpregna-3,5-diene-17β-ol

norethisterone acetate
51-98-9

norethisterone acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / acetone; water / 10 °C
2: dmap; pyridine / 1,2-dichloro-ethane / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride / acetone; water / 10 °C
2: dmap; dicyclohexyl-carbodiimide / chloroform / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride / acetone; water / 10 °C
2: dmap; triethylamine / dichloromethane / 50 °C
View Scheme
C24H33NO

C24H33NO

norethisterone acetate
51-98-9

norethisterone acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid / water; 2-methyltetrahydrofuran / 0 °C
2: dmap; pyridine / 1,2-dichloro-ethane / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid / water; 2-methyltetrahydrofuran / 0 °C
2: dmap; dicyclohexyl-carbodiimide / chloroform / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid / water; 2-methyltetrahydrofuran / 0 °C
2: dmap; triethylamine / dichloromethane / 50 °C
View Scheme
estra-4-ene-3,17-dione
734-32-7

estra-4-ene-3,17-dione

norethisterone acetate
51-98-9

norethisterone acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine hydrochloride / 30 °C
2: potassium tert-butylate / acetone / 0 °C
3: hydrogenchloride / tetrahydrofuran; water / 50 °C
4: dmap; pyridine / 1,2-dichloro-ethane / 0 °C
View Scheme
Multi-step reaction with 4 steps
1: pyridine hydrochloride / 30 °C
2: potassium tert-butylate / acetone / 0 °C
3: hydrogenchloride / tetrahydrofuran; water / 50 °C
4: dmap; dicyclohexyl-carbodiimide / chloroform / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: pyridine hydrochloride / 30 °C
2: potassium tert-butylate / acetone / 0 °C
3: hydrogenchloride / tetrahydrofuran; water / 50 °C
4: dmap; triethylamine / dichloromethane / 50 °C
View Scheme
3-methoxy-19-norandrosta-3,5-dien-17-one
17976-34-0

3-methoxy-19-norandrosta-3,5-dien-17-one

norethisterone acetate
51-98-9

norethisterone acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium tert-butylate / acetone / 0 °C
2: hydrogenchloride / tetrahydrofuran; water / 50 °C
3: dmap; pyridine / 1,2-dichloro-ethane / 0 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium tert-butylate / acetone / 0 °C
2: hydrogenchloride / tetrahydrofuran; water / 50 °C
3: dmap; dicyclohexyl-carbodiimide / chloroform / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium tert-butylate / acetone / 0 °C
2: hydrogenchloride / tetrahydrofuran; water / 50 °C
3: dmap; triethylamine / dichloromethane / 50 °C
View Scheme
3-ethoxy-19-nor-3,5-androstadiene-17-one
2863-88-9

3-ethoxy-19-nor-3,5-androstadiene-17-one

norethisterone acetate
51-98-9

norethisterone acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium 2-methylpropan-2-olate / tetrahydrofuran / 20 °C
2: hydrogenchloride / acetone; water / 10 °C
3: dmap; pyridine / 1,2-dichloro-ethane / 0 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium 2-methylpropan-2-olate / tetrahydrofuran / 20 °C
2: hydrogenchloride / acetone; water / 10 °C
3: dmap; dicyclohexyl-carbodiimide / chloroform / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium 2-methylpropan-2-olate / tetrahydrofuran / 20 °C
2: hydrogenchloride / acetone; water / 10 °C
3: dmap; triethylamine / dichloromethane / 50 °C
View Scheme
(8R,9S,10R,13S,14S)-13-Methyl-3-pyrrolidin-1-yl-1,2,7,8,9,10,11,12,13,14,15,16-dodecahydro-cyclopenta[a]phenanthren-17-one

(8R,9S,10R,13S,14S)-13-Methyl-3-pyrrolidin-1-yl-1,2,7,8,9,10,11,12,13,14,15,16-dodecahydro-cyclopenta[a]phenanthren-17-one

norethisterone acetate
51-98-9

norethisterone acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium ethoxide / toluene / 50 °C
2: sulfuric acid / water; 2-methyltetrahydrofuran / 0 °C
3: dmap; pyridine / 1,2-dichloro-ethane / 0 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium ethoxide / toluene / 50 °C
2: sulfuric acid / water; 2-methyltetrahydrofuran / 0 °C
3: dmap; dicyclohexyl-carbodiimide / chloroform / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium ethoxide / toluene / 50 °C
2: sulfuric acid / water; 2-methyltetrahydrofuran / 0 °C
3: dmap; triethylamine / dichloromethane / 50 °C
View Scheme
C21H28O2

C21H28O2

norethisterone acetate
51-98-9

norethisterone acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / tetrahydrofuran; water / 50 °C
2: dmap; pyridine / 1,2-dichloro-ethane / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride / tetrahydrofuran; water / 50 °C
2: dmap; dicyclohexyl-carbodiimide / chloroform / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride / tetrahydrofuran; water / 50 °C
2: dmap; triethylamine / dichloromethane / 50 °C
View Scheme
norethisterone acetate
51-98-9

norethisterone acetate

17β-acetoxy-21,21-dibromo-19-nor-17α-pregn-4-ene-3,20-dione
40228-41-9

17β-acetoxy-21,21-dibromo-19-nor-17α-pregn-4-ene-3,20-dione

Conditions
ConditionsYield
With water; N-bromoacetamide In tert-butyl alcohol for 4h; Ambient temperature;96%
norethisterone acetate
51-98-9

norethisterone acetate

17β-acetoxy-17α-iodoethynyl-4-estren-3-one

17β-acetoxy-17α-iodoethynyl-4-estren-3-one

Conditions
ConditionsYield
With silver nitrate In tetrahydrofuran81%
norethisterone acetate
51-98-9

norethisterone acetate

3,21-dioxo-19-norpregna-4,17(20)-dien-20-yl acetate
445379-31-7

3,21-dioxo-19-norpregna-4,17(20)-dien-20-yl acetate

Conditions
ConditionsYield
With oxygen; potassium tetrabromopalladate In 1,2-dimethoxyethane; water at 65℃; for 3h;80%
norethisterone acetate
51-98-9

norethisterone acetate

1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate

1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate

C28H38O3

C28H38O3

Conditions
ConditionsYield
With copper(I) phenylacetylenide; copper acetylacetonate; triethylamine; copper(l) chloride In tetrahydrofuran at 25℃; for 16h; Irradiation; Inert atmosphere;78%
norethisterone acetate
51-98-9

norethisterone acetate

methyl 3-azidobenzoate
93066-93-4

methyl 3-azidobenzoate

methyl 3-[4-(17-acetoxy-13-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1H-1,2,3-triazol-1-yl]benzoate

methyl 3-[4-(17-acetoxy-13-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1H-1,2,3-triazol-1-yl]benzoate

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 8h; Inert atmosphere;75%
para-diiodobenzene
624-38-4

para-diiodobenzene

norethisterone acetate
51-98-9

norethisterone acetate

1,4-bis(19-nor-17α-ethynyltestosterone-17β-acetate)benzene
1239157-10-8

1,4-bis(19-nor-17α-ethynyltestosterone-17β-acetate)benzene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 4h; Sonogashira coupling; Inert atmosphere; Reflux;71%
3-azidobenzoic acid
1843-35-2

3-azidobenzoic acid

norethisterone acetate
51-98-9

norethisterone acetate

3-[4-(17-acetoxy-13-methyl-3-oxo-2,3,6,7,8, 9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1H-1,2,3-triazol-1-yl]benzoic acid

3-[4-(17-acetoxy-13-methyl-3-oxo-2,3,6,7,8, 9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1H-1,2,3-triazol-1-yl]benzoic acid

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 8h; Inert atmosphere;70%
norethisterone acetate
51-98-9

norethisterone acetate

17,17a-dimethyl-D-homogona-4,13,15,17(17a)-tetraen-3-one
99998-43-3

17,17a-dimethyl-D-homogona-4,13,15,17(17a)-tetraen-3-one

Conditions
ConditionsYield
With formic acid at 90℃; for 1h; Heating;60%
methyl 4-azidobenzoate
20442-96-0

methyl 4-azidobenzoate

norethisterone acetate
51-98-9

norethisterone acetate

methyl 4-[4-(17-acetoxy-13-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1H-1,2,3-triazol-1-yl]benzoate

methyl 4-[4-(17-acetoxy-13-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1H-1,2,3-triazol-1-yl]benzoate

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 8h; Inert atmosphere;60%
4-azidobenzoic acid
6427-66-3

4-azidobenzoic acid

norethisterone acetate
51-98-9

norethisterone acetate

4-[4-(17-acetoxy-13-methyl-3-oxo-2,3,6,7,8, 9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1H-1,2,3-triazol-1-yl]benzoic acid

4-[4-(17-acetoxy-13-methyl-3-oxo-2,3,6,7,8, 9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1H-1,2,3-triazol-1-yl]benzoic acid

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 8h; Inert atmosphere;55%
norethisterone acetate
51-98-9

norethisterone acetate

2-azido-benzoic acid methyl ester
16714-23-1

2-azido-benzoic acid methyl ester

methyl 2-[4-(17-acetoxy-13-methyl-3-oxo 2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1H-1,2,3-triazol-1-yl]benzoate

methyl 2-[4-(17-acetoxy-13-methyl-3-oxo 2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1H-1,2,3-triazol-1-yl]benzoate

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 8h; Inert atmosphere;50%
2-azidobenzoic acid
31162-13-7

2-azidobenzoic acid

norethisterone acetate
51-98-9

norethisterone acetate

2-[4-(17-acetoxy-13-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1H-1,2,3-triazol-1-yl]benzoic acid

2-[4-(17-acetoxy-13-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1H-1,2,3-triazol-1-yl]benzoic acid

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 8h; Inert atmosphere;45%
1,4-dibromotetradeuterobenzene
4165-56-4

1,4-dibromotetradeuterobenzene

norethisterone acetate
51-98-9

norethisterone acetate

C50H54(2)H4O6
1239157-15-3

C50H54(2)H4O6

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 10h; Sonogashira coupling; Inert atmosphere; Reflux;43%
norethisterone acetate
51-98-9

norethisterone acetate

N-bromoacetamide
79-15-2

N-bromoacetamide

17-acetoxy-19-nor-17βH-pregn-4-ene-3,20-dione
66964-58-7

17-acetoxy-19-nor-17βH-pregn-4-ene-3,20-dione

Conditions
ConditionsYield
With tert-butyl alcohol und Erwaermen des Reaktionsprodukts mit Zink, Essigsaeure und Natriumacetat;
pentan-1-ol
71-41-0

pentan-1-ol

norethisterone acetate
51-98-9

norethisterone acetate

Acetic acid (8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-3-pentyloxy-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Acetic acid (8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-3-pentyloxy-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions
ConditionsYield
(i) HC(OEt)3, TsOH, EtOH, THF, (ii) /BRN= 1730975/, benzene; Multistep reaction;
n-heptan1ol
111-70-6

n-heptan1ol

norethisterone acetate
51-98-9

norethisterone acetate

Acetic acid (8R,9S,10R,13S,14S,17R)-17-ethynyl-3-heptyloxy-13-methyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Acetic acid (8R,9S,10R,13S,14S,17R)-17-ethynyl-3-heptyloxy-13-methyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions
ConditionsYield
(i) HC(OEt)3, TsOH, EtOH, THF, (ii) /BRN= 1731686/, benzene; Multistep reaction;
Cyclopentanol
96-41-3

Cyclopentanol

norethisterone acetate
51-98-9

norethisterone acetate

3-(cyclopentyloxy)-19-nor-17α-pregna-3,5-dien-20-yn-17-ol acetate

3-(cyclopentyloxy)-19-nor-17α-pregna-3,5-dien-20-yn-17-ol acetate

Conditions
ConditionsYield
(i) HC(OEt)3, TsOH, EtOH, THF, (ii) /BRN= 1900556/, benzene; Multistep reaction;
norethisterone acetate
51-98-9

norethisterone acetate

17α-Ethinyl-17β-acetoxy-Δ4-oestren-3-N-chlorimin

17α-Ethinyl-17β-acetoxy-Δ4-oestren-3-N-chlorimin

Conditions
ConditionsYield
(i) MeNH2, MeOH, (ii) aq. Ca(OCl)2, NH3, OTs; Multistep reaction;
norethisterone acetate
51-98-9

norethisterone acetate

trichloroacetic acid anhydride
4124-31-6

trichloroacetic acid anhydride

17β-Acetoxy-17α-ethinyl-3-trichloracetoxy-Δ3.5-oestradien
22223-94-5

17β-Acetoxy-17α-ethinyl-3-trichloracetoxy-Δ3.5-oestradien

chloroform
67-66-3

chloroform

norethisterone acetate
51-98-9

norethisterone acetate

17α-Aethinyl-6-formyl-3-chlor-19-nor-Δ3.5-androstadien-17β-ol-acetat
16375-03-4

17α-Aethinyl-6-formyl-3-chlor-19-nor-Δ3.5-androstadien-17β-ol-acetat

Conditions
ConditionsYield
With N,N-dimethyl-formamide; trichlorophosphate In Trichloroethylene
norethisterone acetate
51-98-9

norethisterone acetate

17α-Ethinyl-3-chlor-19-nor-Δ3,5-androstadien-17β-ol-acetat
13647-61-5

17α-Ethinyl-3-chlor-19-nor-Δ3,5-androstadien-17β-ol-acetat

Conditions
ConditionsYield
With N,N-dimethyl-formamide; trichlorophosphate In chloroform; Trichloroethylene
norethisterone acetate
51-98-9

norethisterone acetate

21-hydroxy-19-norpregna-4,16-diene-3,20-dione
42224-77-1

21-hydroxy-19-norpregna-4,16-diene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80 percent / O2 / K2[PdBr4] / H2O; 1,2-dimethoxy-ethane / 3 h / 65 °C
2: 80 percent / DBU / ethyl acetate / 60 °C
3: 85 percent / K2CO3; water / methanol; tetrahydrofuran / 0.25 h / 20 °C
View Scheme
norethisterone acetate
51-98-9

norethisterone acetate

16α,17α,21-trihydroxy-19-norpregn-4-ene-3,20-dione
148022-19-9

16α,17α,21-trihydroxy-19-norpregn-4-ene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 80 percent / O2 / K2[PdBr4] / H2O; 1,2-dimethoxy-ethane / 3 h / 65 °C
2: 80 percent / DBU / ethyl acetate / 60 °C
3: 85 percent / K2CO3; water / methanol; tetrahydrofuran / 0.25 h / 20 °C
4: 55 percent / OsO4 / pyridine
View Scheme
Multi-step reaction with 4 steps
1: 80 percent / O2 / K2[PdBr4] / H2O; 1,2-dimethoxy-ethane / 3 h / 65 °C
2: 80 percent / DBU / ethyl acetate / 60 °C
3: 85 percent / formic acid; KMnO4 / acetone; H2O / 0 °C
4: 84 percent / K2CO3; water / methanol; tetrahydrofuran / 0.25 h / 20 °C
View Scheme
norethisterone acetate
51-98-9

norethisterone acetate

3,20-dioxo-19-norpregna-4,16-dien-21-yl acetate
40228-35-1

3,20-dioxo-19-norpregna-4,16-dien-21-yl acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / O2 / K2[PdBr4] / H2O; 1,2-dimethoxy-ethane / 3 h / 65 °C
2: 80 percent / DBU / ethyl acetate / 60 °C
View Scheme
Multi-step reaction with 3 steps
1: 96 percent / N-bromoacetamide, water / 2-methyl-propan-2-ol / 4 h / Ambient temperature
2: 98 percent / trimethyl phosphite / nitromethane / 1 h / Ambient temperature
3: 63 percent / dimethylformamide / 2 h / 120 °C
View Scheme

19-Norethindrone acetate Consensus Reports

IARC Cancer Review: Animal Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 21 (1979),p. 441.(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) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 6 (1974),p. 179.(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) . EPA Genetic Toxicology Program.

19-Norethindrone acetate Specification

1. Introduction of 19-Norethindrone acetate
19-Norethindrone acetate is one kind of white or almost white crystalline. The IUPAC name of this chemical is [(8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate. We can also call it "Norethindrone Acetate". It belongs to Active Pharmaceutical Ingredients;Acetylenes;Biochemistry;Functionalized Acetylenes;Hydroxyketosteroids;Steroids;Intermediates & Fine Chemicals;Pharmaceuticals;Steroid and Hormone. Solubility: Insoluble in cold water, hot water. Besides, it should be stored in a closed cool and dry place.

2. Properties of 19-Norethindrone acetate
Physical properties about 19-Norethindrone acetate are:
(1)ACD/LogP: 3.99; (2)ACD/LogD (pH 5.5): 3.99; (3)ACD/LogD (pH 7.4): 3.99; (4)ACD/BCF (pH 5.5): 632.47; (5)ACD/BCF (pH 7.4): 632.47; (6)ACD/KOC (pH 5.5): 3520.35; (7)ACD/KOC (pH 7.4): 3520.35; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 43.37 Å2; (11)Index of Refraction: 1.555; (12)Molar Refractivity: 95.13 cm3; (13)Molar Volume: 296.1 cm3; (14)Polarizability: 37.71×10-24cm3; (15)Surface Tension: 46.1 dyne/cm; (16)Density: 1.14 g/cm3; (17)Flash Point: 197.1 °C; (18)Enthalpy of Vaporization: 71.43 kJ/mol; (19)Boiling Point: 454.7 °C at 760 mmHg; (20)Vapour Pressure: 1.87E-08 mmHg at 25°C.

3. Structure Descriptors of 19-Norethindrone acetate
(1)SMILES: O=C4\C=C3/[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@]1(C#C)OC(=O)C)[C@@H]2CC3)C)CC4
(2)InChI: InChI=1/C22H28O3/c1-4-22(25-14(2)23)12-10-20-19-7-5-15-13-16(24)6-8-17(15)18(19)9-11-21(20,22)3/h1,13,17-20H,5-12H2,2-3H3/t17-,18+,19+,20-,21-,22-/m0/s1
(3)InChIKey: IMONTRJLAWHYGT-ZCPXKWAGBE
(4)Std. InChI: InChI=1S/C22H28O3/c1-4-22(25-14(2)23)12-10-20-19-7-5-15-13-16(24)6-8-17(15)18(19)9-11-21(20,22)3/h1,13,17-20H,5-12H2,2-3H3/t17-,18+,19+,20-,21-,22-/m0/s1
(5)Std. InChIKey: IMONTRJLAWHYGT-ZCPXKWAGSA-N

4. Physical Properties of 19-Norethindrone acetate

Physical Property Value Units Temp (deg C) Source
Melting Point 161.5 deg C   EXP
log P (octanol-water) 3.990 (none)   EST
Water Solubility 5.35 mg/L 25 EXP
Atmospheric OH Rate Constant 1.10E-10 cm3/molecule-sec 25 EST

5. Safety Information of 19-Norethindrone acetate
Risk Codes:40-48
40: Limited evidence of a carcinogenic effect
41: Risk of serious damage to eyes
42: May cause sensitization by inhalation
43: May cause sensitization by skin contact
44: Risk of explosion if heated under confinement
45: May cause cancer
46: May cause heritable genetic damage
48: Danger of serious damage to health by prolonged exposure
Safety Statements 36/37
36: Wear suitable protective clothing
37: Wear suitable gloves
Hence, When you are using this chemical, please be cautious about it as the following: It is danger of serious damage to health by prolonged exposure. When you are using it, wear suitable protective clothing and gloves.

6. Use of 19-Norethindrone acetate
19-Norethindrone acetate can be used as progesterone medicines for irregular menstruation, uterine functional bleeding, endometriosis proge. Norethindrone and acetate in combination with estrogen as contraceptive (oral). It is reasonably anticipated to be a human carcinogen.

7. Preparation of 19-Norethindrone acetate
Norethindrone and Acetic anhydride can used to produce 19-Norethindrone acetate under the consideration of DMAP.

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