Product Name

  • Name

    Nomegestrol 17-acetate

  • EINECS 261-379-8
  • CAS No. 58652-20-3
  • Article Data7
  • CAS DataBase
  • Density 1.16 g/cm3
  • Solubility
  • Melting Point
  • Formula C23H30O4
  • Boiling Point 507.3 °C at 760 mmHg
  • Molecular Weight 370.489
  • Flash Point 219.8 °C
  • Transport Information
  • Appearance
  • Safety 61
  • Risk Codes 63-50
  • Molecular Structure Molecular Structure of 58652-20-3 (Nomegestrol 17-acetate)
  • Hazard Symbols N
  • Synonyms 6-Methyl-17a-acetoxy-D6-19-norprogesterone;Lutenyl;Nomegestrol acetate;Org 10486-0;Surplant;TX 066;Uniplant;Nomegestrol 17-acetate;
  • PSA 60.44000
  • LogP 4.18520

Synthetic route

17α-acetoxy-6-methylene-19-norpregn-4-ene-3,20-dione
58652-19-0

17α-acetoxy-6-methylene-19-norpregn-4-ene-3,20-dione

nomegestrol acetate
58652-20-3

nomegestrol acetate

Conditions
ConditionsYield
With [Rh(Binap)2]+[ClO4]- In tetrahydrofuran at 80℃; for 0.5h; Solvent; Temperature; Sealed tube; Inert atmosphere;99%
With palladium 10% on activated carbon; acetic acid In ethanol at 72 - 75℃; for 0.166667h; Temperature; Inert atmosphere; Large scale;90.2%
With 5%-palladium/activated carbon In tetrahydrofuran; ethanol for 0.75h; Reflux;77%
C23H32O4

C23H32O4

nomegestrol acetate
58652-20-3

nomegestrol acetate

Conditions
ConditionsYield
With chloranil In 1,4-dioxane at 90 - 95℃; Solvent; Temperature;77.8%
17α-hydroxy-3-methoxy-19-norpregna-1,3,5(10)-trien-20-one
1624-58-4

17α-hydroxy-3-methoxy-19-norpregna-1,3,5(10)-trien-20-one

nomegestrol acetate
58652-20-3

nomegestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: toluene-4-sulfonic acid; trimethyl orthoformate / dichloromethane / 2 h / 20 °C
2: sodium; ammonia / ethanol; water; tetrahydrofuran; tert-butyl alcohol / -60 °C / Inert atmosphere
3: hydrogenchloride / water; tetrahydrofuran / 0.33 h / 60 °C
4: toluene-4-sulfonic acid / 24 h / 20 °C
5: toluene-4-sulfonic acid / tetrahydrofuran / 24 h / 20 °C
6: trichlorophosphate / -10 °C
7: sodium tetrahydroborate / methanol / 20 °C
8: 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 0.75 h / Reflux
View Scheme
20,20-(ethylenedioxy)-3-methoxy-17α-hydroxy-19-norpregna-1,3,5(10)-triene
14328-46-2

20,20-(ethylenedioxy)-3-methoxy-17α-hydroxy-19-norpregna-1,3,5(10)-triene

nomegestrol acetate
58652-20-3

nomegestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: sodium; ammonia / ethanol; water; tetrahydrofuran; tert-butyl alcohol / -60 °C / Inert atmosphere
2: hydrogenchloride / water; tetrahydrofuran / 0.33 h / 60 °C
3: toluene-4-sulfonic acid / 24 h / 20 °C
4: toluene-4-sulfonic acid / tetrahydrofuran / 24 h / 20 °C
5: trichlorophosphate / -10 °C
6: sodium tetrahydroborate / methanol / 20 °C
7: 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 0.75 h / Reflux
View Scheme
17-alpha-Hydroxy-19-norprogesterone
2137-18-0

17-alpha-Hydroxy-19-norprogesterone

nomegestrol acetate
58652-20-3

nomegestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: toluene-4-sulfonic acid / 24 h / 20 °C
2: toluene-4-sulfonic acid / tetrahydrofuran / 24 h / 20 °C
3: trichlorophosphate / -10 °C
4: sodium tetrahydroborate / methanol / 20 °C
5: 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 0.75 h / Reflux
View Scheme
Estrone
53-16-7

Estrone

nomegestrol acetate
58652-20-3

nomegestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: sodium hydroxide / acetone; water / 2 h / Reflux
2.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C
3.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C
4.1: sodium methylate / methanol / Reflux
4.2: 2 h / Reflux
5.1: toluene-4-sulfonic acid; trimethyl orthoformate / dichloromethane / 2 h / 20 °C
6.1: sodium; ammonia / ethanol; water; tetrahydrofuran; tert-butyl alcohol / -60 °C / Inert atmosphere
7.1: hydrogenchloride / water; tetrahydrofuran / 0.33 h / 60 °C
8.1: toluene-4-sulfonic acid / 24 h / 20 °C
9.1: toluene-4-sulfonic acid / tetrahydrofuran / 24 h / 20 °C
10.1: trichlorophosphate / -10 °C
11.1: sodium tetrahydroborate / methanol / 20 °C
12.1: 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 0.75 h / Reflux
View Scheme
17α-acetoxy-19-norpregna-4-ene-3,20-dione
31981-44-9

17α-acetoxy-19-norpregna-4-ene-3,20-dione

nomegestrol acetate
58652-20-3

nomegestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: toluene-4-sulfonic acid / tetrahydrofuran / 24 h / 20 °C
2: trichlorophosphate / -10 °C
3: sodium tetrahydroborate / methanol / 20 °C
4: 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 0.75 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / dichloromethane / 25 - 30 °C
2: sodium hydroxide; dihydrogen peroxide / methanol / 20 - 25 °C
3: magnesium / chloroform; diethyl ether / 30 - 55 °C
4: chloranil / 1,4-dioxane / 90 - 95 °C
View Scheme
Multi-step reaction with 4 steps
1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / dichloromethane / 25 - 30 °C
2: sodium hydroxide; dihydrogen peroxide / methanol / 20 - 25 °C
3: magnesium / tetrahydrofuran / 30 - 55 °C
4: chloranil / 1,4-dioxane / 90 - 95 °C
View Scheme
Multi-step reaction with 4 steps
1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / dichloromethane / 25 - 30 °C
2: sodium hydroxide; dihydrogen peroxide / methanol / 20 - 25 °C
3: magnesium / toluene / 30 - 55 °C
4: chloranil / 1,4-dioxane / 90 - 95 °C
View Scheme
3-ethoxy-17α-acetoxy-19-norpregna-3,5-diene-20-one

3-ethoxy-17α-acetoxy-19-norpregna-3,5-diene-20-one

nomegestrol acetate
58652-20-3

nomegestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: trichlorophosphate / -10 °C
2: sodium tetrahydroborate / methanol / 20 °C
3: 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 0.75 h / Reflux
View Scheme
6-formyl-3-ethoxy-17α-acetoxy-19-norpregna-3,5-diene-20-one
147508-40-5

6-formyl-3-ethoxy-17α-acetoxy-19-norpregna-3,5-diene-20-one

nomegestrol acetate
58652-20-3

nomegestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol / 20 °C
2: 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 0.75 h / Reflux
View Scheme
estrone 3-methyl ether
1624-62-0

estrone 3-methyl ether

nomegestrol acetate
58652-20-3

nomegestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C
2.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C
3.1: sodium methylate / methanol / Reflux
3.2: 2 h / Reflux
4.1: toluene-4-sulfonic acid; trimethyl orthoformate / dichloromethane / 2 h / 20 °C
5.1: sodium; ammonia / ethanol; water; tetrahydrofuran; tert-butyl alcohol / -60 °C / Inert atmosphere
6.1: hydrogenchloride / water; tetrahydrofuran / 0.33 h / 60 °C
7.1: toluene-4-sulfonic acid / 24 h / 20 °C
8.1: toluene-4-sulfonic acid / tetrahydrofuran / 24 h / 20 °C
9.1: trichlorophosphate / -10 °C
10.1: sodium tetrahydroborate / methanol / 20 °C
11.1: 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 0.75 h / Reflux
View Scheme
C22H32O4

C22H32O4

nomegestrol acetate
58652-20-3

nomegestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: hydrogenchloride / water; tetrahydrofuran / 0.33 h / 60 °C
2: toluene-4-sulfonic acid / 24 h / 20 °C
3: toluene-4-sulfonic acid / tetrahydrofuran / 24 h / 20 °C
4: trichlorophosphate / -10 °C
5: sodium tetrahydroborate / methanol / 20 °C
6: 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 0.75 h / Reflux
View Scheme
mestranol
72-33-3

mestranol

nomegestrol acetate
58652-20-3

nomegestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C
2.1: sodium methylate / methanol / Reflux
2.2: 2 h / Reflux
3.1: toluene-4-sulfonic acid; trimethyl orthoformate / dichloromethane / 2 h / 20 °C
4.1: sodium; ammonia / ethanol; water; tetrahydrofuran; tert-butyl alcohol / -60 °C / Inert atmosphere
5.1: hydrogenchloride / water; tetrahydrofuran / 0.33 h / 60 °C
6.1: toluene-4-sulfonic acid / 24 h / 20 °C
7.1: toluene-4-sulfonic acid / tetrahydrofuran / 24 h / 20 °C
8.1: trichlorophosphate / -10 °C
9.1: sodium tetrahydroborate / methanol / 20 °C
10.1: 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 0.75 h / Reflux
View Scheme
3-methoxy-21-(phenylsulfinyl)-19-norpregna-1(2),3(4),5(10),17(20),20-pentaene

3-methoxy-21-(phenylsulfinyl)-19-norpregna-1(2),3(4),5(10),17(20),20-pentaene

nomegestrol acetate
58652-20-3

nomegestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: sodium methylate / methanol / Reflux
1.2: 2 h / Reflux
2.1: toluene-4-sulfonic acid; trimethyl orthoformate / dichloromethane / 2 h / 20 °C
3.1: sodium; ammonia / ethanol; water; tetrahydrofuran; tert-butyl alcohol / -60 °C / Inert atmosphere
4.1: hydrogenchloride / water; tetrahydrofuran / 0.33 h / 60 °C
5.1: toluene-4-sulfonic acid / 24 h / 20 °C
6.1: toluene-4-sulfonic acid / tetrahydrofuran / 24 h / 20 °C
7.1: trichlorophosphate / -10 °C
8.1: sodium tetrahydroborate / methanol / 20 °C
9.1: 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 0.75 h / Reflux
View Scheme
C26H38O6

C26H38O6

nomegestrol acetate
58652-20-3

nomegestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide; dihydrogen peroxide / methanol / 20 - 25 °C
2: magnesium / tetrahydrofuran / 30 - 55 °C
3: chloranil / 1,4-dioxane / 90 - 95 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide; dihydrogen peroxide / methanol / 20 - 25 °C
2: magnesium / toluene / 30 - 55 °C
3: chloranil / 1,4-dioxane / 90 - 95 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide; dihydrogen peroxide / methanol / 20 - 25 °C
2: magnesium / chloroform; diethyl ether / 30 - 55 °C
3: chloranil / 1,4-dioxane / 90 - 95 °C
View Scheme
C26H38O7

C26H38O7

nomegestrol acetate
58652-20-3

nomegestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: magnesium / tetrahydrofuran / 30 - 55 °C
2: chloranil / 1,4-dioxane / 90 - 95 °C
View Scheme
Multi-step reaction with 2 steps
1: magnesium / toluene / 30 - 55 °C
2: chloranil / 1,4-dioxane / 90 - 95 °C
View Scheme
nomegestrol acetate
58652-20-3

nomegestrol acetate

6-α-methyl-3,20-dioxo-19-norpregna-4-en-17-yl acetate
32420-14-7

6-α-methyl-3,20-dioxo-19-norpregna-4-en-17-yl acetate

Conditions
ConditionsYield
With palladium 10% on activated carbon In ethanol; cyclohexane for 3h; Reflux;71%
With 5%-palladium/activated carbon; cyclohexene In ethanol for 2h; Reflux;34%
nomegestrol acetate
58652-20-3

nomegestrol acetate

A

(3R,3aS,5aS,5bR,8'R,8aR,9R,9'S,10'R,12aR,12bS,13'S,14'S,17'R)-3,17'-diacetyl-3a,13'-dimethyl-3',8-dioxo-1',2,2',3,3',3a,4,5,5a,5b,6,7,7',8,8',8a,9',10,10',11,11',12,12',12a,12b, 13',14',15',16',17'-triacontahydro-1H-spiro[benzo[fg]cyclopenta[a]anthracene-9,6'-cyclopenta[a]phenanthrene]-3,17'-diyl diacetate

(3R,3aS,5aS,5bR,8'R,8aR,9R,9'S,10'R,12aR,12bS,13'S,14'S,17'R)-3,17'-diacetyl-3a,13'-dimethyl-3',8-dioxo-1',2,2',3,3',3a,4,5,5a,5b,6,7,7',8,8',8a,9',10,10',11,11',12,12',12a,12b, 13',14',15',16',17'-triacontahydro-1H-spiro[benzo[fg]cyclopenta[a]anthracene-9,6'-cyclopenta[a]phenanthrene]-3,17'-diyl diacetate

B

(3R,3aS,5aS,5bR,8'R,8aR,9S,9'S,10'R,12aR,12bS,13'S,14'S,17'R)-3,17'-diacetyl-3a,13'-dimethyl-3',8-dioxo-1',2,2',3,3',3a,4,5,5a,5b,6,7,7',8,8',8a,9',10,10',11,11',12,12',12a,12b, 13',14',15',16',17'-triacontahydro-1H-spiro[benzo[fg]cyclopenta[a]anthracene-9,6'-cyclopenta[a]phenanthrene]-3,17'-diyl diacetate

(3R,3aS,5aS,5bR,8'R,8aR,9S,9'S,10'R,12aR,12bS,13'S,14'S,17'R)-3,17'-diacetyl-3a,13'-dimethyl-3',8-dioxo-1',2,2',3,3',3a,4,5,5a,5b,6,7,7',8,8',8a,9',10,10',11,11',12,12',12a,12b, 13',14',15',16',17'-triacontahydro-1H-spiro[benzo[fg]cyclopenta[a]anthracene-9,6'-cyclopenta[a]phenanthrene]-3,17'-diyl diacetate

Conditions
ConditionsYield
In toluene for 12h; Inert atmosphere; Reflux;A 0.41 g
B 2.5 g

Nomegestrol 17-acetate Specification

The Nomegestrol 17-acetate is an organic compound with the formula C23H30O4. The systematic name of this chemical is (17α)-17-acetyl-6-methyl-3-oxoestra-4,6-dien-17-yl acetate. With the CAS registry number 58652-20-3 and EINECS 261-379-8, it is also named as Nomegestrol acetate. The classification codes are Hormone; Human Data; Prevention of pregnancy in women who elect to use a hormonal contraceptive as a method of contraception; Reproductive Effect.

hysical properties about Nomegestrol 17-acetate are: (1)ACD/LogP: 3.467; (2)ACD/LogD (pH 5.5): 3.47; (3)ACD/LogD (pH 7.4): 3.47; (4)ACD/BCF (pH 5.5): 254.25; (5)ACD/BCF (pH 7.4): 254.25; (6)ACD/KOC (pH 5.5): 1833.56; (7)ACD/KOC (pH 7.4): 1833.56; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 3; (10)Index of Refraction: 1.554; (11)Molar Refractivity: 101.755 cm3; (12)Molar Volume: 317.431 cm3; (13)Polarizability: 40.339 10-24cm3; (14)Surface Tension: 44.8489990234375 dyne/cm; (15)Density: 1.167 g/cm3; (16)Flash Point: 219.846 °C; (17)Enthalpy of Vaporization: 77.738 kJ/mol; (18)Boiling Point: 507.306 °C at 760 mmHg

People can use the following data to convert to the molecule structure. 
1. SMILES:O=C4\C=C3\C(=C/[C@@H]1[C@H](CC[C@@]2([C@@](OC(=O)C)(C(=O)C)CC[C@@H]12)C)[C@H]3CC4)C
2. InChI:InChI=1/C23H30O4/c1-13-11-20-18(17-6-5-16(26)12-19(13)17)7-9-22(4)21(20)8-10-23(22,14(2)24)27-15(3)25/h11-12,17-18,20-21H,5-10H2,1-4H3/t17-,18-,20-,21+,22+,23+/m1/s1
3. InChIKey:IIVBFTNIGYRNQY-YQLZSBIMBA

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 2gm/kg (2000mg/kg)   Drugs of the Future. Vol. 9, Pg. 657, 1984.
mouse LD50 oral > 2gm/kg (2000mg/kg)   Drugs of the Future. Vol. 9, Pg. 657, 1984.
rat LD50 intraperitoneal > 2gm/kg (2000mg/kg)   Drugs of the Future. Vol. 9, Pg. 657, 1984.
rat LD50 oral > 2gm/kg (2000mg/kg)   Drugs of the Future. Vol. 9, Pg. 657, 1984.
women TDLo oral 1050ug/kg/21D (1.05mg/kg) ENDOCRINE: ESTROGENIC

ENDOCRINE: CHANGE IN LH

ENDOCRINE: EFFECT ON MENSTRUAL CYSLE		 British Journal of Obstetrics and Gynaecology. Vol. 94, Pg. 1199, 1987.

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