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Name	Desogestrel	EINECS	258-929-4
CAS No.	54024-22-5	Density	1.07 g/cm³
PSA	20.23000	LogP	4.86970
Solubility	practically insoluble in water	Melting Point	109-110 ºC
Formula	C₂₂H₃₀O	Boiling Point	428.3 ºC at 760 mmHg
Molecular Weight	310.48	Flash Point	187.9 ºC
Transport Information	N/A	Appearance	white to off-white crystalline powder
Safety	24/25	Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
Synonyms	Desogen;18,19-Dinorpregn-4-en-20-yn-17-ol,13-ethyl-11-methylene-, (17a)-;3-Ethyl-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-17-ol;	Article Data	20

Desogestrel Synthetic route

: C24H38O2Si

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water Solvent; Reflux;	96.5%

: 1216963-74-4
lithium acetylide-ethylenediamine complex

: 54024-21-4
11-methylene-18a-homo-estr-4-en-17-one

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
In dimethyl sulfoxide at 20℃; for 21h;	89%

: 54024-21-4
11-methylene-18a-homo-estr-4-en-17-one

: 1066-54-2
trimethylsilylacetylene

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Stage #1: trimethylsilylacetylene With n-hexyllithium In tetrahydrofuran; hexane at -5℃; for 0.5h; Stage #2: 11-methylene-18a-homo-estr-4-en-17-one In tetrahydrofuran; hexane at 0 - 5℃; for 1h;	89%

: 54024-21-4
11-methylene-18a-homo-estr-4-en-17-one

: 74-86-2
acetylene

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
With lithium; ethylenediamine In tetrahydrofuran at 25℃; for 2h; continuous flow of ethyne;	85%
Stage #1: acetylene With lithium In ethylenediamine at 20℃; for 2h; Peterson olefination; Stage #2: 11-methylene-18a-homo-estr-4-en-17-one In tetrahydrofuran at 20℃; for 2h; Further stages;	83%
Stage #1: acetylene With N,N,N,N,-tetramethylethylenediamine; lithium for 2h; Stage #2: 11-methylene-18a-homo-estr-4-en-17-one In tetrahydrofuran at 20℃; for 2h; Stage #3: With hydrogenchloride; water In tetrahydrofuran	83%

: 116930-33-7
C24H32OS2

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
With sodium In tetrahydrofuran; ammonia at -4℃; for 1h;	58%

: 1216963-74-4
lithium acetylide-ethylenediamine complex

: 54024-21-4
11-methylene-18a-homo-estr-4-en-17-one

A: 54024-22-5
desogestrel

B: 16β-OH desogestrel

Conditions

Conditions	Yield
In tetrahydrofuran; ethylenediamine at 10 - 20℃; for 4h;	A 0.220 g B 0.060 g

: 220332-76-3
(+)-(1S,3aS,7aS)-hexahydro-1-(tert-butyldimethylsiloxy)-7a-ethyl-5-indanone

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1: 80 percent / NaH, MeOH / tetrahydrofuran; hexane / 1 h / Heating 2: 1.) NaH, 2.) n-BuLi 3: 1.) trifluoroacetic acid, 2.) K2CO3, MeOH / 1.) CH2Cl2, 23 deg C, 24 h, 2.) 23 deg C, 1 h 4: 73 percent / imidazole / dimethylformamide / 12 h / 50 °C 5: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C 6: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C 7: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 8: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 9: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 10: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 11: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 12: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

Yield

Multi-step reaction with 12 steps
1: 80 percent / NaH, MeOH / tetrahydrofuran; hexane / 1 h / Heating
2: 1.) NaH, 2.) n-BuLi
3: 1.) trifluoroacetic acid, 2.) K2CO3, MeOH / 1.) CH2Cl2, 23 deg C, 24 h, 2.) 23 deg C, 1 h
4: 73 percent / imidazole / dimethylformamide / 12 h / 50 °C
5: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C
6: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C
7: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C
8: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C
9: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C
10: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating
11: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C
12: 1.) n-BuLi, 2.) Ce(III) chloride
View Scheme

: 220332-77-4
(+)-(1S,3aS,7aS)-3a,4,7,7a-tetrahydro-1-(tert-butyldimethylsiloxy)-6-carbomethoxy-7a-ethyl-5-hydroxyindane

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: 1.) NaH, 2.) n-BuLi 2: 1.) trifluoroacetic acid, 2.) K2CO3, MeOH / 1.) CH2Cl2, 23 deg C, 24 h, 2.) 23 deg C, 1 h 3: 73 percent / imidazole / dimethylformamide / 12 h / 50 °C 4: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C 5: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C 6: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 7: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 8: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 9: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 10: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 11: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

Yield

Multi-step reaction with 11 steps
1: 1.) NaH, 2.) n-BuLi
2: 1.) trifluoroacetic acid, 2.) K2CO3, MeOH / 1.) CH2Cl2, 23 deg C, 24 h, 2.) 23 deg C, 1 h
3: 73 percent / imidazole / dimethylformamide / 12 h / 50 °C
4: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C
5: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C
6: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C
7: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C
8: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C
9: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating
10: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C
11: 1.) n-BuLi, 2.) Ce(III) chloride
View Scheme

: 54024-20-3
(+)-13β-ethyl-11-methylenegona-4-en-17β-ol

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 2: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

: 220332-82-1
(+)-13β-ethyl-17β-hydroxy-11-methylenegona-4-en-3-one

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 2: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 3: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 4: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

Desogestrel Chemical Properties

IUPAC Name: (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylidene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
Molecular Formula: C₂₂H₃₀O
Molecular Weight: 310.48 g/mol
SMILES: C1C(=C)[C@H]2[C@H]([C@@H]3CC[C@@](C#C)(O)[C@@]13CC)CCC=1[C@@H]2CCCC1
InChI: InChI=1/C22H30O/c1-4-21-14-15(3)20-17-9-7-6-8-16(17)10-11-18(20)19(21)12-13-22(21,23)5-2/h2,8,17-20,23H,3-4,6-7,9-14H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1
EINECS: 258-929-4
Classification Code: Contraceptive Agents; Contraceptive Agents, Female; Contraceptives, Oral; Contraceptives, oral, synthetic; Hormone; Hormones; Hormones, Hormone Substitutes, and Hormone Antagonists; Human Data; Progestin; Progestins; Reproductive Control Agents; Reproductive Effect
Product Categories: Intermediates & Fine Chemicals; Pharmaceuticals; Steroids
Index of Refraction: 1.566
Molar Refractivity: 94.23 cm³
Molar Volume: 288.7 cm³
Polarizability: 37.35×10^-24 cm³
Surface Tension: 43.9 dyne/cm
Density: 1.07 g/cm³
Flash Point: 187.9 °C
Enthalpy of Vaporization: 78.92 kJ/mol
Boiling Point: 428.3 °C at 760 mmHg
Melting Point: 109-110 °C
Vapour Pressure of Desogestrel (CAS NO.54024-22-5): 3.92E-09 mmHg at 25 °C

Desogestrel Uses

Desogestrel (CAS NO.54024-22-5) is a molecule used in hormonal contraceptives and as a progestogen with low androgenic potency.

Desogestrel Safety Profile

Human reproductive effects by ingestion: changes in menstrual cycle and female fertility. Experimental reproductive effects. A steroid. When heated to decomposition it emits acrid smoke and fumes.

Desogestrel Specification

Desogestrel (CAS NO.54024-22-5), its Synonyms are Desogen ; 13-Ethyl-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-17-ol ; Cerazette ; Desogestrelum ; 18,19-Dinorpregn-4-en-20-yn-17-ol, 13-ethyl-11-methylene-, (17alpha)- .

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