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Name	Gestodene	EINECS	262-145-8
CAS No.	60282-87-3	Density	1.15 g/cm³
PSA	37.30000	LogP	3.65860
Solubility	N/A	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	N/A	Appearance	white crystalline solid
Safety	36/37-24/25	Risk Codes	62
Molecular Structure		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;	Article Data	13

Gestodene Synthetic route

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

: 60282-87-3
gestodene

Conditions

Conditions	Yield
With hydrogenchloride In acetone at 20℃; for 0.75h;	90%

: 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

: 60282-87-3
gestodene

Conditions

Conditions	Yield
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%

: 1323980-05-7
3-ethoxy-18-methyl-estra-3,5,15-trien-17-one

: 4301-14-8
acetylenemagnesium bromide

: 60282-87-3
gestodene

Conditions

Conditions	Yield
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%

: 74177-02-9
17α-Ethinyl-3,3-ethylendithio-18-methyl-4,15-estradien-17β-ol

: 60282-87-3
gestodene

Conditions

Conditions	Yield
With calcium carbonate; methyl iodide In methanol; water for 20h; Heating;	68%

: 107-21-1
ethylene glycol

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

: 74-86-2
acetylene

: 60282-87-3
gestodene

Conditions

Conditions	Yield
Yield given. Multistep reaction;

: 77410-09-4
18-Methyl-4,15-estradien-3,17-dion

: 74-86-2
acetylene

: 60282-87-3
gestodene

Conditions

Conditions	Yield
With n-butyllithium 1.) THF/hexane, -70 deg C, 10 min, 2.) -70 deg C, 1 h; Yield given. Multistep reaction;

: 104934-00-1
15α-Acetoxy-3-methoxy-18-methyl-3,5-estradien-17-on

: 74-86-2
acetylene

: 60282-87-3
gestodene

Conditions

Conditions	Yield
Yield given. Multistep reaction;

: 21800-83-9
13β-ethyl-gon-4-en-3,17-dione

: 60282-87-3
gestodene

Conditions

Conditions	Yield
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

: 60282-87-3
gestodene

Conditions

Conditions	Yield
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

: 60282-87-3
gestodene

Conditions

Conditions	Yield
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

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^-24cm³
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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