Product Name

  • Name

    Gestodene

  • EINECS 262-145-8
  • CAS No. 60282-87-3
  • Article Data13
  • CAS DataBase
  • Density 1.15 g/cm3
  • Solubility
  • Melting Point 190-192 °C
  • Formula C21H26O2
  • Boiling Point 462.7 °C at 760 mmHg
  • Molecular Weight 310.436
  • Flash Point 196.9 °C
  • Transport Information
  • Appearance white crystalline solid
  • Safety 36/37-24/25
  • Risk Codes 62
  • Molecular Structure Molecular Structure of 60282-87-3 (Gestodene)
  • Hazard Symbols Xn
  • Synonyms Gestinol;13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregna-4,15-dien-20-yn-3-one;SHB 331;18,19-Dinorpregna-4,15-dien-20-yn-3-one,13-ethyl-17-hydroxy-, (17a)-;7-alpha-Ethinyl-13-ethyl-17-beta-hydroxy-4,15-gonadien-3-one ; Gestodeno;
  • PSA 37.30000
  • LogP 3.65860

Synthetic route

3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-17α-ethnyl-17β-hydroxy-18-methyl-5,15-estradiene

3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-17α-ethnyl-17β-hydroxy-18-methyl-5,15-estradiene

gestodene
60282-87-3

gestodene

Conditions
ConditionsYield
With hydrogenchloride In acetone at 20℃; for 0.75h;90%
17α-ethynyl-18-methyl-3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-5,15-estradien-17β-ol
64133-14-8

17α-ethynyl-18-methyl-3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-5,15-estradien-17β-ol

3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-17α-ethnyl-17β-hydroxy-18-methyl-10,15-estradiene

3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-17α-ethnyl-17β-hydroxy-18-methyl-10,15-estradiene

gestodene
60282-87-3

gestodene

Conditions
ConditionsYield
Stage #1: 17α-ethynyl-18-methyl-3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-5,15-estradien-17β-ol; 3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-17α-ethnyl-17β-hydroxy-18-methyl-10,15-estradiene With water; hydrogenchloride In acetone at 20℃; for 0.75h;
Stage #2: With sodium hydrogencarbonate In water; acetone pH=7; Product distribution / selectivity;		90%
3-ethoxy-18-methyl-estra-3,5,15-trien-17-one
1323980-05-7

3-ethoxy-18-methyl-estra-3,5,15-trien-17-one

acetylenemagnesium bromide
4301-14-8

acetylenemagnesium bromide

gestodene
60282-87-3

gestodene

Conditions
ConditionsYield
Stage #1: 3-ethoxy-18-methyl-estra-3,5,15-trien-17-one; acetylenemagnesium bromide In tetrahydrofuran; 2-MeTHF at 20 - 25℃; for 2h;
Stage #2: With hydrogenchloride In ethanol; water at 7 - 10℃; for 2h;		80%
17α-Ethinyl-3,3-ethylendithio-18-methyl-4,15-estradien-17β-ol
74177-02-9

17α-Ethinyl-3,3-ethylendithio-18-methyl-4,15-estradien-17β-ol

gestodene
60282-87-3

gestodene

Conditions
ConditionsYield
With calcium carbonate; methyl iodide In methanol; water for 20h; Heating;68%
ethylene glycol
107-21-1

ethylene glycol

15α-Acetoxy-18-methyl-4-estren-3,17-dion
104933-97-3

15α-Acetoxy-18-methyl-4-estren-3,17-dion

acetylene
74-86-2

acetylene

gestodene
60282-87-3

gestodene

Conditions
ConditionsYield
Yield given. Multistep reaction;
...Expand
18-Methyl-4,15-estradien-3,17-dion
77410-09-4

18-Methyl-4,15-estradien-3,17-dion

acetylene
74-86-2

acetylene

gestodene
60282-87-3

gestodene

Conditions
ConditionsYield
With n-butyllithium 1.) THF/hexane, -70 deg C, 10 min, 2.) -70 deg C, 1 h; Yield given. Multistep reaction;
15α-Acetoxy-3-methoxy-18-methyl-3,5-estradien-17-on
104934-00-1

15α-Acetoxy-3-methoxy-18-methyl-3,5-estradien-17-on

acetylene
74-86-2

acetylene

gestodene
60282-87-3

gestodene

Conditions
ConditionsYield
Yield given. Multistep reaction;
13β-ethyl-gon-4-en-3,17-dione
21800-83-9

13β-ethyl-gon-4-en-3,17-dione

gestodene
60282-87-3

gestodene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 90 percent / triethyl orthoformate; p-TsOH / CH2Cl2 / 3 h / 10 °C
2.1: t-BuOK / tetrahydrofuran / 0.17 h / 20 °C
2.2: tetrahydrofuran / 2 h / 20 °C
3.1: Et3N / xylene / 2.5 h / 140 °C
4.1: 94 percent / tetrahydrofuran / 2 h / 0 °C
5.1: 90 percent / aq. HCl / acetone / 0.75 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1: 90 percent / triethyl orthoformate; p-TsOH / CH2Cl2 / 3 h / 10 °C
2: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 - 20 °C
3: MCPBA / CH2Cl2 / 0.5 h / -78 °C
4: Et3N / xylene / 2.5 h / 140 °C
5: 94 percent / tetrahydrofuran / 2 h / 0 °C
6: 90 percent / aq. HCl / acetone / 0.75 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 77.2 percent / mushroom Penicillium raistrickii (ATCC 10490) / H2O; various solvent(s) / 70 h / 30 °C
2: 96 percent / pyridine / 1 h
View Scheme
3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-18-methyl-5,15-estradien-17-one

3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-18-methyl-5,15-estradien-17-one

gestodene
60282-87-3

gestodene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 94 percent / tetrahydrofuran / 2 h / 0 °C
2: 90 percent / aq. HCl / acetone / 0.75 h / 20 °C
View Scheme
18-methyl-3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-5-estern-17-one

18-methyl-3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-5-estern-17-one

gestodene
60282-87-3

gestodene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: t-BuOK / tetrahydrofuran / 0.17 h / 20 °C
1.2: tetrahydrofuran / 2 h / 20 °C
2.1: Et3N / xylene / 2.5 h / 140 °C
3.1: 94 percent / tetrahydrofuran / 2 h / 0 °C
4.1: 90 percent / aq. HCl / acetone / 0.75 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 - 20 °C
2: MCPBA / CH2Cl2 / 0.5 h / -78 °C
3: Et3N / xylene / 2.5 h / 140 °C
4: 94 percent / tetrahydrofuran / 2 h / 0 °C
5: 90 percent / aq. HCl / acetone / 0.75 h / 20 °C
View Scheme
C30H40O3S

C30H40O3S

gestodene
60282-87-3

gestodene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: MCPBA / CH2Cl2 / 0.5 h / -78 °C
2: Et3N / xylene / 2.5 h / 140 °C
3: 94 percent / tetrahydrofuran / 2 h / 0 °C
4: 90 percent / aq. HCl / acetone / 0.75 h / 20 °C
View Scheme
3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-18-methyl-16ξ-phenylsulfoxide-5-estren-17-one

3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-18-methyl-16ξ-phenylsulfoxide-5-estren-17-one

gestodene
60282-87-3

gestodene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N / xylene / 2.5 h / 140 °C
2: 94 percent / tetrahydrofuran / 2 h / 0 °C
3: 90 percent / aq. HCl / acetone / 0.75 h / 20 °C
View Scheme
15α-Hydroxy-18-methyl-4-estren-3,17-dion
60919-46-2

15α-Hydroxy-18-methyl-4-estren-3,17-dion

gestodene
60282-87-3

gestodene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 96 percent / pyridine / 1 h
View Scheme
Multi-step reaction with 3 steps
1: 96 percent / pyridine / 1 h
2: 84 percent / 4-CH3-C6H6-SO3H*C5H5N / 6 h / Heating
View Scheme
Multi-step reaction with 5 steps
1: 98 percent / BF3*Et2O / methanol / Ambient temperature
2: pyridine / 3.5 h / 0 °C
3: NaOAc / pyridine; dimethylformamide / 20 h / Ambient temperature
4: 1.) 15 percent BuLi / 1.) hexane, THF, 0 deg C, 2.) 30 min
5: 68 percent / CH3I, CaCO3 / methanol; H2O / 20 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: pyridine / 3.5 h / 0 °C
2: NaOAc / pyridine; dimethylformamide / 20 h / Ambient temperature
3: 1.) 15 percent BuLi / 1.) THF/hexane, -70 deg C, 10 min, 2.) -70 deg C, 1 h
View Scheme
3,3-Ethylendithio-18-methyl-4,15-estradien-17-on
74177-01-8

3,3-Ethylendithio-18-methyl-4,15-estradien-17-on

gestodene
60282-87-3

gestodene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) 15 percent BuLi / 1.) hexane, THF, 0 deg C, 2.) 30 min
2: 68 percent / CH3I, CaCO3 / methanol; H2O / 20 h / Heating
View Scheme
3,3-Ethylendithio-15α-hydroxy-18-methyl-4-estren-17-on
74177-00-7

3,3-Ethylendithio-15α-hydroxy-18-methyl-4-estren-17-on

gestodene
60282-87-3

gestodene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / 3.5 h / 0 °C
2: NaOAc / pyridine; dimethylformamide / 20 h / Ambient temperature
3: 1.) 15 percent BuLi / 1.) hexane, THF, 0 deg C, 2.) 30 min
4: 68 percent / CH3I, CaCO3 / methanol; H2O / 20 h / Heating
View Scheme
15α-Acetoxy-18-methyl-4-estren-3,17-dion
104933-97-3

15α-Acetoxy-18-methyl-4-estren-3,17-dion

gestodene
60282-87-3

gestodene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 84 percent / 4-CH3-C6H6-SO3H*C5H5N / 6 h / Heating
View Scheme
Multi-step reaction with 3 steps
1.1: toluene-4-sulfonic acid / ethanol / 1 h / 20 °C
2.1: toluene-4-sulfonic acid; orthoformic acid triethyl ester / 1 h / 20 °C
2.2: 2 h / 40 °C
3.1: tetrahydrofuran; 2-MeTHF / 2 h / 20 - 25 °C
3.2: 2 h / 7 - 10 °C
View Scheme
Methanesulfonic acid (8R,9S,10R,13S,14S,15S)-13-ethyl-3,17-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-15-yl ester
104934-02-3

Methanesulfonic acid (8R,9S,10R,13S,14S,15S)-13-ethyl-3,17-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-15-yl ester

gestodene
60282-87-3

gestodene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaOAc / pyridine; dimethylformamide / 20 h / Ambient temperature
2: 1.) 15 percent BuLi / 1.) THF/hexane, -70 deg C, 10 min, 2.) -70 deg C, 1 h
View Scheme
C22H32O4S3
104934-03-4

C22H32O4S3

gestodene
60282-87-3

gestodene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NaOAc / pyridine; dimethylformamide / 20 h / Ambient temperature
2: 1.) 15 percent BuLi / 1.) hexane, THF, 0 deg C, 2.) 30 min
3: 68 percent / CH3I, CaCO3 / methanol; H2O / 20 h / Heating
View Scheme
15α-Acetoxy-3-methoxy-18-methyl-3,5-estradien-17-on
104934-00-1

15α-Acetoxy-3-methoxy-18-methyl-3,5-estradien-17-on

gestodene
60282-87-3

gestodene

Conditions
ConditionsYield
Product distribution / selectivity;
ethyl bromide
74-96-4

ethyl bromide

acetylene
74-86-2

acetylene

gestodene
60282-87-3

gestodene

Conditions
ConditionsYield
With oxalic acid; magnesium In tetrahydrofuran; methanol; water
15α-acetoxy-3-ethoxy-18-methyl-estra-3,5-dien-17-one
106620-51-3

15α-acetoxy-3-ethoxy-18-methyl-estra-3,5-dien-17-one

gestodene
60282-87-3

gestodene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: toluene-4-sulfonic acid; orthoformic acid triethyl ester / 1 h / 20 °C
1.2: 2 h / 40 °C
2.1: tetrahydrofuran; 2-MeTHF / 2 h / 20 - 25 °C
2.2: 2 h / 7 - 10 °C
View Scheme
15α-Acetoxy-18-methyl-4-estren-3,17-dion
104933-97-3

15α-Acetoxy-18-methyl-4-estren-3,17-dion

acetylene
74-86-2

acetylene

gestodene
60282-87-3

gestodene

Conditions
ConditionsYield
Stage #1: 15α-Acetoxy-18-methyl-4-estren-3,17-dion With hydrogenchloride; propylene glycol In 1,4-dioxane; 1,2-dimethoxyethane at -20℃; for 4h;
Stage #2: With toluene-4-sulfonic acid; trimethyl orthoformate In methanol at 20℃; for 3h;
Stage #3: acetylene Further stages;		8.17 g
gestodene
60282-87-3

gestodene

17α-Bromethinyl-17β-hydroxy-18-methyl-4,15-oestradien-3-on
91781-31-6

17α-Bromethinyl-17β-hydroxy-18-methyl-4,15-oestradien-3-on

Conditions
ConditionsYield
With N-Bromosuccinimide; silver nitrate In acetone for 0.25h; Ambient temperature;82%
gestodene
60282-87-3

gestodene

17β-Hydroxy-17α-iodethinyl-18-methyl-4,15-oestradien-3-on
91798-46-8

17β-Hydroxy-17α-iodethinyl-18-methyl-4,15-oestradien-3-on

Conditions
ConditionsYield
With N-iodo-succinimide; silver nitrate In acetone for 0.25h; Ambient temperature;77%
gestodene
60282-87-3

gestodene

13-β-ethyl-18,19-dinorpregna-4,14,16-trien-3,20-dione

13-β-ethyl-18,19-dinorpregna-4,14,16-trien-3,20-dione

Conditions
ConditionsYield
With hydrogenchloride at 80℃; for 2h;1.55 g
gestodene
60282-87-3

gestodene

gestodene propionate

gestodene propionate

Conditions
ConditionsYield
With 4-pyrrolidin-1-ylpyridine In pyridine; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dichloromethane; propionic acid anhydride
pentanoic anhydride
2082-59-9

pentanoic anhydride

gestodene
60282-87-3

gestodene

gestodene valerate

gestodene valerate

Conditions
ConditionsYield
With 4-pyrrolidin-1-ylpyridine In pyridine; water
gestodene
60282-87-3

gestodene

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

17α-ethynyl-17β-hexadecanoyloxy-18-methyl-4,15-estradien-3-one

17α-ethynyl-17β-hexadecanoyloxy-18-methyl-4,15-estradien-3-one

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane; acetone; benzene
...Expand
undecylenic acid
112-37-8

undecylenic acid

gestodene
60282-87-3

gestodene

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

17α-ethynyl-18-methyl-17β-undecanoyloxy-4,15-estradien-3-one

17α-ethynyl-18-methyl-17β-undecanoyloxy-4,15-estradien-3-one

Conditions
ConditionsYield
In benzene
...Expand
gestodene
60282-87-3

gestodene

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

17α-ethynyl-18-methyl-17β-octanoyloxy-4,15-estradien-3-one

17α-ethynyl-18-methyl-17β-octanoyloxy-4,15-estradien-3-one

Conditions
ConditionsYield
In dichloromethane; acetone; benzene
gestodene
60282-87-3

gestodene

17β-acetoxy-17α-ethynyl-18-methyl-4,15-estradien-3-one

17β-acetoxy-17α-ethynyl-18-methyl-4,15-estradien-3-one

Conditions
ConditionsYield
With acetic anhydride In 2,3,5-trimethyl-pyridine; hydrogenchloride

Gestodene Chemical Properties


IUPAC Name: (8R,9S,10R,13S,14S,17R)-13-Ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14-decahydrocyclopenta[a]phenanthren-3-one
Molecular Formula: C21H26O2
Molecular Weight: 310.43 g/mol
SMILES: C1[C@@]2([C@@H]([C@@H]3[C@@H]([C@@H]4C(=CC(=O)CC4)CC3)C1)C=C[C@]2(C#C)O)CC
InChI: InChI=1/C21H26O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,10,12-13,16-19,23H,3,5-9,11H2,1H3/t16?,17?,18?,19?,20?,21-/m0/s1
EINECS: 262-145-8
Classification Code: Contraceptive Agents; Contraceptive Agents, Female; Contraceptives, Oral; Contraceptives, oral, synthetic; Hormone; Hormones; Hormones, Hormone Substitutes, and Hormone Antagonists; Progestin; Progestins; Reproductive Control Agents; Reproductive Effect
Product Categories: Miscellaneous Biochemicals; Hormone; Intermediates & Fine Chemicals; Pharmaceuticals; Steroids
Index of Refraction: 1.588
Molar Refractivity: 90.09 cm3
Molar Volume: 267.6 cm3
Polarizability: 35.71×10-24 cm3
Surface Tension: 49.7 dyne/cm
Density: 1.15 g/cm3
Flash Point: 196.9 °C
Enthalpy of Vaporization: 83.47 kJ/mol
Boiling Point: 462.7 °C at 760 mmHg
Melting Point: 190-192 °C
Vapour Pressure of Gestodene (CAS NO.60282-87-3): 1.66E-10 mmHg at 25 °C

Gestodene Uses

 Gestodene (CAS NO.60282-87-3) is used as orally active gestogen with progesterone-like profile of activity and is used as a contraceptive.

Gestodene Specification

 Gestodene (CAS NO.60282-87-3), its Synonyms are 13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregna-4,15-dien-20-yn-3-one ; 17-alpha-Ethinyl-13-ethyl-17-beta-hydroxy-4,15-gonadien-3-one ; Gestodeno ; Gestodenum ; 18,19-Dinorpregna-4,15-dien-20-yn-3-one, 13-ethyl-17-hydroxy-, (17-alpha)- ; Pregna-4,15-dien-20-yn-3-one, 13-ethyl-17-hydroxy-18,19-dinor-, (17alpha)- . It is white crystalline solid.

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