52-76-6

Basic information

• Product Name: Lynestrenol
• Synonyms: 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
• CAS NO: 52-76-6
• Molecular Formula: C₂₀H₂₈O
• Molecular Weight: 284.44
• EINECS: 200-151-4
• Product Categories: Steroids;Hormone;Intracellular receptor
• Mol File: 52-76-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 158°C
• Boiling Point: 366.92°C (rough estimate)
• Flash Point: 176.9 °C
• Appearance: /
• Density: 1.0083 (rough estimate)
• Vapor Pressure: 4.77E-08mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Practically insoluble in water, soluble in acetone and in ethanol (96 per cent).
• PKA: 13.12±0.40(Predicted)
• Merck: 14,5629
• CAS DataBase Reference: Lynestrenol(CAS DataBase Reference)
• NIST Chemistry Reference: Lynestrenol(52-76-6)
• EPA Substance Registry System: Lynestrenol(52-76-6)

Safety Data

• RTECS: RC8964300
• Hazardous Substances Data: 52-76-6(Hazardous Substances Data)

Usage

Chemical Properties

White or almost white, crystalline powder.

Uses

Different sources of media describe the Uses of 52-76-6 differently. You can refer to the following data:
1. Progestogen;Antioestrogen
2. Lynestrenol is an orally available progestogen hormone used in contraception to avoid hereditary angiodema as well as in treatment of ischemic stroke.

Brand name

Anacycline 101;Anacylin 101;Anacylin 28;Ancylin;Athilyn;Endometril;Exluton (a);Fysiognens;Fysionorm;Gestrol;Lindiol 2.5;Lyn_ratiopharm;Lyn_ratiophram_sequenz;Lyndeol;Lyndile tt;Lyndiol e.;Lyndiolett;Lynoenstrenol;Lyn-ratiopharm;Mini pregnon;Minifol;Minilyn;Neo lyndiol;Neo-lindiol;Neo-lynobol;Nonovulet;Noracyclin 22;Normophasic;Novostat;Org 485-50;Orgaluton;Orgametrol;Ovamezzo;Ovanone;Ovanon-e;Ovariostat;Ovoresta micro;Ovostat-28;Ovostat-micro;Phasicon;Physiostat;Physistat;Pregnon-28;Restovar.

World Health Organization (WHO)

Lynestrenol, a synthetic progestogen, was introduced in the early 1960s as a component in oral contraceptive preparations. In 1967, as a result of new regulations required by the United States Food and Drug Administration, lynestrenol was submitted to long-term toxicity studies and by the early 1970s it was shown to be associated with an increased incidence of mammary tumours in beagle bitches which led to its withdrawal by at least one regulatory authority. Subsequently the validity of the beagle bitch model as a predictor of carcinogenicity of steroid contraceptives has been contested by many national regulatory authorities and lynestrenol remains available in some countries for contraceptive and other purposes. (Reference: (WHODI) WHO Drug Information, 1-3, 5-7, 1984)

Safety Profile

An experimental teratogen.Experimental reproductive effects. Human reproductiveeffects by ingestion and implant routes: menstrual cyclechanges or disorders, female fertility index, other fertilitychanges and effects on females. Questionable carcinoge

InChI:InChI=1/C20H28O/c1-3-20(21)13-11-18-17-9-8-14-6-4-5-7-15(14)16(17)10-12-19(18,20)2/h1,6,15-18,21H,4-5,7-13H2,2H3/t15-,16+,17+,18-,19-,20+/m0/s1

Synthetic route

4-Estren-17-one (3646-28-4) + potassium acetylenide → lynestrenol (52-76-6)

Conditions	Yield
With isopropyl alcohol

(+)-17β-hydroxyester-4-ene (3646-30-8) → lynestrenol (52-76-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetone; CrO3; aqueous H2SO4 2: isopropyl alcohol View Scheme

norethisterone (68-22-4) + pyrographite (7440-44-0) → lynestrenol (52-76-6)

Conditions	Yield
In acetone

lynestrenol (52-76-6) + allyl bromide (106-95-6) → 17-O-allyllynestrenol

Conditions	Yield
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) + bromopentene (1119-51-3) → 17-O-(4-penten-1-yl)lynestrenol

Conditions	Yield
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) → (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	Yield
With lithium aluminium tetrahydride; aluminium trichloride In tetrahydrofuran

lynestrenol (52-76-6) → (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 + (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	Yield
With hematoporphyrin In methanol at 15℃; Rate constant; Irradiation; pH 7.7;

lynestrenol (52-76-6) → 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)

Conditions	Yield
With sulfuric acid; mercury(II) oxide

lynestrenol (52-76-6) → C20H27(2)H7O

Conditions	Yield
With deuterium; palladium on activated charcoal In ethanol

lynestrenol (52-76-6) → (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	Yield
With sulfuric acid; mercury(II) oxide

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

lynestrenol (52-76-6) → (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	Yield
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) → 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)

Conditions	Yield
Multi-step reaction with 2 steps 1: HgO, aq. H2SO4 2: Py / N,N-dimethyl-acetamide View Scheme

lynestrenol (52-76-6) → 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	Yield
Multi-step reaction with 2 steps 1: HgO, aq. H2SO4 2: Py View Scheme

lynestrenol (52-76-6) → (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	Yield
Multi-step reaction with 2 steps 1: HgO, aq. H2SO4 2: Ac2O, Py View Scheme

lynestrenol (52-76-6) → 19-nor-17α-pregn-4-en-20-yn-3β,6β,17β-triol (1253379-05-3) + 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-10β,17β-diol (1236-00-6)

Conditions	Yield
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

lynestrenol (52-76-6) → (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	Yield
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) → (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	Yield
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) → (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

Yield

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) → (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 + 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

Yield

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

Upstream product

• 68-22-4 norethisterone 
• 7440-44-0 pyrographite 
• 3646-30-8 (+)-17β-hydroxyester-4-ene 
• 3646-28-4 4-Estren-17-one 

Downstream Products

• 1253379-05-3 19-nor-17α-pregn-4-en-20-yn-3β,6β,17β-triol 
• 51724-44-8 19-nor-17α-pregn-4-en-20-yn-3-one-6β,17β-diol 
• 1236-00-6 19-nor-17α-pregn-4-en-20-yn-3-one-10β,17β-diol 

Relevant articles and documents

Process for the production of 3-deoxy-4-ene steroids

A process for the production of 3-deoxy-4-ene steroids of the general formula I STR1 is described, in which R1, R2 and R3 mean a hydrogen atom or a methyl group, R4 represents a lower alkyl group, a phenyl group or a free, esterified or etherified hydroxy group, R5 symbolizes a hydrogen atom, a vinyl group or the grouping --C CR6 with R6 meaning a hydrogen atom, an alkyl group with a maximum of 4 carbon atoms or a halogen atom, X represents a methylene group, a fluoromethylene group, an ethylidene group or a vinylidene group, Y and U represent a methylene group or an ethylidene group and Z symbolizes a methylene group, an ethylidene group, a vinylidene group, a chloromethylene group or a hydroxymethylene group and in which the bonds represent three single bonds or one double bond and two single bonds or a conjugated double bond.