Product Name

  • Name

    Lynestrenol

  • EINECS 200-151-4
  • CAS No. 52-76-6
  • Article Data4
  • CAS DataBase
  • Density 1.08 g/cm3
  • Solubility
  • Melting Point 158 °C
  • Formula C20H28O
  • Boiling Point 399.6 °C at 760 mmHg
  • Molecular Weight 284.442
  • Flash Point 176.9 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 52-76-6 (Lynestrenol)
  • Hazard Symbols
  • Synonyms 19-Nor-17a-pregn-4-en-20-yn-17-ol(6CI,8CI);17a-Ethynyl-17b-hydroxyestr-4-ene;3-Desoxy-17a-ethinyl-19-nortestosterone;Exlutena;Exluton;Fysionorm;NSC 73879;Orgametrol;Physiostat;D4-17a-Ethinylestren-17b-ol;
  • PSA 20.23000
  • LogP 4.31350

Synthetic route

4-Estren-17-one
3646-28-4

4-Estren-17-one

potassium acetylenide

potassium acetylenide

lynestrenol
52-76-6

lynestrenol

Conditions
ConditionsYield
With isopropyl alcohol
(+)-17β-hydroxyester-4-ene
3646-30-8

(+)-17β-hydroxyester-4-ene

lynestrenol
52-76-6

lynestrenol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetone; CrO3; aqueous H2SO4
2: isopropyl alcohol
View Scheme
norethisterone
68-22-4

norethisterone

pyrographite
7440-44-0

pyrographite

lynestrenol
52-76-6

lynestrenol

Conditions
ConditionsYield
In acetone
lynestrenol
52-76-6

lynestrenol

allyl bromide
106-95-6

allyl bromide

17-O-allyllynestrenol

17-O-allyllynestrenol

Conditions
ConditionsYield
Stage #1: lynestrenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1.5h; Inert atmosphere;
Stage #2: allyl bromide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 16h; Inert atmosphere;		93%
lynestrenol
52-76-6

lynestrenol

bromopentene
1119-51-3

bromopentene

17-O-(4-penten-1-yl)lynestrenol

17-O-(4-penten-1-yl)lynestrenol

Conditions
ConditionsYield
Stage #1: lynestrenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1.5h; Inert atmosphere;
Stage #2: bromopentene In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 16h; Inert atmosphere;		49%
lynestrenol
52-76-6

lynestrenol

(8R,9S,10R,13S,14S)-13-Methyl-17-vinylidene-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene

(8R,9S,10R,13S,14S)-13-Methyl-17-vinylidene-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene

Conditions
ConditionsYield
With lithium aluminium tetrahydride; aluminium trichloride In tetrahydrofuran
lynestrenol
52-76-6

lynestrenol

A

(5R,8R,9S,10R,13S,14S,17R)-17-Ethynyl-13-methyl-1,4,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-5,17-diol

(5R,8R,9S,10R,13S,14S,17R)-17-Ethynyl-13-methyl-1,4,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-5,17-diol

B

(4S,8R,9S,10R,13S,14S,17R)-17-Ethynyl-13-methyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-4,17-diol

(4S,8R,9S,10R,13S,14S,17R)-17-Ethynyl-13-methyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-4,17-diol

Conditions
ConditionsYield
With hematoporphyrin In methanol at 15℃; Rate constant; Irradiation; pH 7.7;
lynestrenol
52-76-6

lynestrenol

1-((8R,9S,10R,13S,14S,17S)-17-Hydroxy-13-methyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethanone
61625-77-2

1-((8R,9S,10R,13S,14S,17S)-17-Hydroxy-13-methyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethanone

Conditions
ConditionsYield
With sulfuric acid; mercury(II) oxide
lynestrenol
52-76-6

lynestrenol

C20H27(2)H7O

C20H27(2)H7O

Conditions
ConditionsYield
With deuterium; palladium on activated charcoal In ethanol
lynestrenol
52-76-6

lynestrenol

(1S,4aS,4bR,10aR,10bS,12aS)-1-Hydroxy-1,12a-dimethyl-3,4,4a,4b,5,6,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-chrysen-2-one

(1S,4aS,4bR,10aR,10bS,12aS)-1-Hydroxy-1,12a-dimethyl-3,4,4a,4b,5,6,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-chrysen-2-one

Conditions
ConditionsYield
With sulfuric acid; mercury(II) oxide
lynestrenol
52-76-6

lynestrenol

(1R,4aS,4bR,10aR,10bS,12aS)-1,12a-Dimethyl-2-methylene-1,2,3,4,4a,4b,5,6,8,9,10,10a,10b,11,12,12a-hexadecahydro-chrysen-1-ol

(1R,4aS,4bR,10aR,10bS,12aS)-1,12a-Dimethyl-2-methylene-1,2,3,4,4a,4b,5,6,8,9,10,10a,10b,11,12,12a-hexadecahydro-chrysen-1-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HgO, aq. H2SO4
2: (i) NaH, DMSO, (ii) /BRN= 7185930/, THF
View Scheme
lynestrenol
52-76-6

lynestrenol

(8R,9S,10R,13S,14S,17R)-17-Isopropenyl-13-methyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol

(8R,9S,10R,13S,14S,17R)-17-Isopropenyl-13-methyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: HgO, aq. H2SO4
2: Py / N,N-dimethyl-acetamide
3: (i) nBuLi, toluene, (ii) /BRN= 7187106/
View Scheme
lynestrenol
52-76-6

lynestrenol

1-((8R,9S,10R,13S,14S,17S)-13-Methyl-17-trimethylsilanyloxy-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethanone
61625-96-5

1-((8R,9S,10R,13S,14S,17S)-13-Methyl-17-trimethylsilanyloxy-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethanone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HgO, aq. H2SO4
2: Py / N,N-dimethyl-acetamide
View Scheme
lynestrenol
52-76-6

lynestrenol

Acetic acid (1R,4aS,4bR,10aR,10bS,12aS)-1,12a-dimethyl-2-oxo-1,2,3,4,4a,4b,5,6,8,9,10,10a,10b,11,12,12a-hexadecahydro-chrysen-1-yl ester

Acetic acid (1R,4aS,4bR,10aR,10bS,12aS)-1,12a-dimethyl-2-oxo-1,2,3,4,4a,4b,5,6,8,9,10,10a,10b,11,12,12a-hexadecahydro-chrysen-1-yl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HgO, aq. H2SO4
2: Py
View Scheme
lynestrenol
52-76-6

lynestrenol

(1R,4aS,4bR,10aR,10bS,12aS)-1-Hydroxy-1,12a-dimethyl-3,4,4a,4b,5,6,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-chrysen-2-one

(1R,4aS,4bR,10aR,10bS,12aS)-1-Hydroxy-1,12a-dimethyl-3,4,4a,4b,5,6,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-chrysen-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HgO, aq. H2SO4
2: Ac2O, Py
View Scheme
lynestrenol
52-76-6

lynestrenol

A

19-nor-17α-pregn-4-en-20-yn-3β,6β,17β-triol
1253379-05-3

19-nor-17α-pregn-4-en-20-yn-3β,6β,17β-triol

B

19-nor-17α-pregn-4-en-20-yn-3-one-6β,17β-diol
51724-44-8

19-nor-17α-pregn-4-en-20-yn-3-one-6β,17β-diol

C

19-nor-17α-pregn-4-en-20-yn-3-one-10β,17β-diol
1236-00-6

19-nor-17α-pregn-4-en-20-yn-3-one-10β,17β-diol

Conditions
ConditionsYield
With potassium dihydrogenphosphate; D-glucose; sodium chloride In water; acetone; glycerol at 30℃; for 288h; pH=5.6; Microbiological reaction;A 9.7 mg
B 11.2 mg
C 13.4 mg
...Expand
lynestrenol
52-76-6

lynestrenol

(2'S,8R,9S,10R,13S,14S)-13-methyl-3'-vinyl-1,2,3,6,7,8,9,10,11,12,13,14,15,16-tetradecahydro-5'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]

(2'S,8R,9S,10R,13S,14S)-13-methyl-3'-vinyl-1,2,3,6,7,8,9,10,11,12,13,14,15,16-tetradecahydro-5'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1.5 h / 0 °C / Inert atmosphere
1.2: 16 h / 0 - 20 °C / Inert atmosphere
2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 120 °C / Inert atmosphere; Sealed tube; Microwave irradiation
View Scheme
lynestrenol
52-76-6

lynestrenol

(2'S,8R,9S,10R,13S,14S)-13-methyl-3'-vinyl-1,2,3,6,6',7,7',8,9,10,11,12,13,14,15,16-hexadecahydro-5'H-spiro[cyclopenta[a]phenanthrene-17,2'-oxepine]

(2'S,8R,9S,10R,13S,14S)-13-methyl-3'-vinyl-1,2,3,6,6',7,7',8,9,10,11,12,13,14,15,16-hexadecahydro-5'H-spiro[cyclopenta[a]phenanthrene-17,2'-oxepine]

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1.5 h / 0 °C / Inert atmosphere
1.2: 16 h / 0 - 20 °C / Inert atmosphere
2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 170 °C / Inert atmosphere; Sealed tube; Microwave irradiation
View Scheme
lynestrenol
52-76-6

lynestrenol

(3'S,5a'S,8R,8a'R,8b'S,9S,10R,13S,14S)-13-methyl-7'-phenyl-1,1',2,3,5',5a',6,7,8,8b',9,10,11,12,13,14,15,16-octadecahydrospiro[cyclopenta[a]phenanthrene-17,3'-furo[3,4-e]isoindole]-6',8'(7'H,8a'H)-dione

(3'S,5a'S,8R,8a'R,8b'S,9S,10R,13S,14S)-13-methyl-7'-phenyl-1,1',2,3,5',5a',6,7,8,8b',9,10,11,12,13,14,15,16-octadecahydrospiro[cyclopenta[a]phenanthrene-17,3'-furo[3,4-e]isoindole]-6',8'(7'H,8a'H)-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1.5 h / 0 °C / Inert atmosphere
1.2: 16 h / 0 - 20 °C / Inert atmosphere
2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 120 °C / Inert atmosphere; Sealed tube; Microwave irradiation
3.1: toluene / 0.58 h / 150 °C / Inert atmosphere
View Scheme
lynestrenol
52-76-6

lynestrenol

A

(3a'S,6'S,8R,9S,10R,10a'S,10b'R,13S,14S)-13-methyl-2'-phenyl-1,2,3,3a',4',6,7,8,8',9,9',10,10',10a',11,12,13,14,15,16-icosahydrospiro[cyclopenta[a]phenanthrene-17,6'-oxepino[4,3-e]isoindole]-1',3'(2'H,10b'H)-dione

(3a'S,6'S,8R,9S,10R,10a'S,10b'R,13S,14S)-13-methyl-2'-phenyl-1,2,3,3a',4',6,7,8,8',9,9',10,10',10a',11,12,13,14,15,16-icosahydrospiro[cyclopenta[a]phenanthrene-17,6'-oxepino[4,3-e]isoindole]-1',3'(2'H,10b'H)-dione

B

13-methyl-2'-phenyl-1,2,3,3a',4',6,7,8,8',9,9',10,10',10a',11,12,13,14,15,16-icosahydrospiro[cyclopenta[a]phenanthrene-17,6'-oxepino[4,3-e]isoindole]-1',3'(2'H,10b'H)-dione

13-methyl-2'-phenyl-1,2,3,3a',4',6,7,8,8',9,9',10,10',10a',11,12,13,14,15,16-icosahydrospiro[cyclopenta[a]phenanthrene-17,6'-oxepino[4,3-e]isoindole]-1',3'(2'H,10b'H)-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1.5 h / 0 °C / Inert atmosphere
1.2: 16 h / 0 - 20 °C / Inert atmosphere
2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 170 °C / Inert atmosphere; Sealed tube; Microwave irradiation
3.1: toluene / 0.58 h / 150 °C / Inert atmosphere
View Scheme

Lynestrenol Chemical Properties

 Chemical Name: Lynestrenol
IUPAC NAME: (8R,9S,10R,13S,14S,17R)-17-Ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
CAS No.: 52-76-6
Molecular Formula: C20H28O
Molecular Weight: 284.44 g/mol
Melting Point: 158°C
Density: 1.08 g/cm3 
Flash Point: 176.9 °C
Boiling Point: 399.6 °C at 760 mmHg
Following is the structure of 19-Nor-17-α-pregn-4-en-20-yn-17-ol (52-76-6):


Product Categories about 19-Nor-17-α-pregn-4-en-20-yn-17-ol (52-76-6) are Steroids ; Hormone ; Intracellular receptor
The chemical synonymous of 19-Nor-17-α-pregn-4-en-20-yn-17-ol (52-76-6) are 4-Estren-17-alpha-ethynyl-17-beta-ol ; 4-Estren-17a-ethinyl-17beta-ol ; 19-Nor-17-alpha-pregn-4-en-20-yn-17-l ; Ethinylestrenol ; Lynoestrenol ; Lynestrenol ; (17-Alpha)-19-norpregn-4-en-20-yn-17-ol ; 17-Alpha-ethinyl-17-beta-hydroxyestr-4-ene

Lynestrenol Consensus Reports

IARC Cancer Review: Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 21 ,1979,p. 407.(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) .

Lynestrenol Safety Profile

An experimental teratogen. Experimental reproductive effects. Human reproductive effects by ingestion and implant routes: menstrual cycle changes or disorders, female fertility index, other fertility changes and effects on females. Questionable carcinogen. Used in oral contraceptives and in the treatment of dysfunctional uterine bleeding. When heated to decomposition it emits acrid smoke and irritating fumes.

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