Tibolone supplier | CasNO.5630-53-5

Name
Tibolone
EINECS 227-069-1
CAS No. 5630-53-5
Article Data12
CAS DataBase
Density 1.13 g/cm³
Solubility
Melting Point 169 °C
Formula C₂₁H₂₈O₂
Boiling Point 447.4 °C at 760 mmHg
Molecular Weight 312.452
Flash Point 190.6 °C
Transport Information UN 3077 9/PG 3
Appearance white solid
Safety 22-24/25-61
Risk Codes 51/53
Molecular Structure
Hazard Symbols N
Synonyms 19-Nor-17a-pregn-5(10)-en-20-yn-3-one, 17-hydroxy-7a-methyl- (7CI,8CI);(7a,17a)-17-Hydroxy-7-methyl-19-norpregn-5(10)-en-20-yn-3-one;7a-Methyl-17a-ethynyl-17b-hydroxy-5(10)-estren-3-one;7a-Methyl-D5,10-norethindrone;Livial;Liviella;Org OD 14;19-Norpregn-5(10)-en-20-yn-3-one,17-hydroxy-7-methyl-, (7a,17a)-;
PSA 37.30000
LogP 3.88260

Synthetic route

: C25H36O4

: 5630-53-5
tibolone

Conditions

Conditions	Yield
With sulfuric acid In water; acetone at 0 - 5℃; for 1h; Industrial scale;	90%

: 105186-33-2
3,3-dimethoxy-7α-methyl-19-nor-17α-pregn-5(10)-en-20-yn-17β-ol

A: 1162-60-3
7α-methyl-17α-ethinyl-17β-hydroxy-4-estren-3-one

B: 5630-53-5
tibolone

C: 105186-34-3
10β-hydroperoxy-17β-hydroxy-7α-methyl-19-nor-17α-pregn-4-en-20-yn-3-one

Conditions

Conditions	Yield
With oxalic acid In ethanol; water at 20℃; for 2h; Yields of byproduct given;	A n/a B 79% C n/a

...Expand

: 15506-05-5
3-Methoxy-7α-methyl-17α-aethinyl-17β-hydroxy-Δ2,5(10)-19-norandrastadien

: 5630-53-5
tibolone

Conditions

Conditions	Yield
Stage #1: 3-Methoxy-7α-methyl-17α-aethinyl-17β-hydroxy-Δ2,5(10)-19-norandrastadien With ascorbic acid In ethanol at 20 - 30℃; for 1h; Activated Carbon Darco G60; Stage #2: With hydrogenchloride In ethanol; water at 20 - 25℃;	78%
With oxalic acid In methanol

: 677299-58-0
7α-methylnorethynodrel ethylene ketal

A: 1162-60-3
7α-methyl-17α-ethinyl-17β-hydroxy-4-estren-3-one

B: 5630-53-5
tibolone

Conditions

Conditions	Yield
Stage #1: 7α-methylnorethynodrel ethylene ketal With formic acid In tetrahydrofuran; ethanol; water at 40 - 60℃; for 1h; Stage #2: With formic acid In methanol for 6h;	A 19% B 63.7%
Stage #1: 7α-methylnorethynodrel ethylene ketal With copper(II) sulfate In methanol; ethanol; water at 73 - 76℃; for 4.5h; Stage #2: With copper(II) sulfate for 0.5h;	A 5.7% B 49%

: 105186-33-2
3,3-dimethoxy-7α-methyl-19-nor-17α-pregn-5(10)-en-20-yn-17β-ol

: 5630-53-5
tibolone

Conditions

Conditions	Yield
With oxalic acid In methanol; water at 25℃; Solvent; Reagent/catalyst; Temperature;	60.6%
In water Product distribution / selectivity; Acidic conditions;

: 105186-32-1
7α-methylestr-5(10)-ene-3,17-dione

: 5630-53-5
tibolone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 86 percent / malonic acid / 24 h / 20 °C 2: 91 percent / potassium tert-butoxide / tetrahydrofuran / 2 h / 0 °C 3: 79 percent / oxalic acid dihydrate / H2O; ethanol / 2 h / 20 °C View Scheme

: 88247-84-1
3,3-dimethoxy-7α-methylestr-5(10)-en-17-one

: 5630-53-5
tibolone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 91 percent / potassium tert-butoxide / tetrahydrofuran / 2 h / 0 °C 2: 79 percent / oxalic acid dihydrate / H2O; ethanol / 2 h / 20 °C View Scheme

: 17β,19-dihydroxy-7-methylandrost-4-en-3-one

: 5630-53-5
tibolone

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 46 percent / CrO3, conc. H2SO4 / H2O; CH2Cl2 / 2.75 h / 30 - 40 °C 2: 98 percent / magnesium methoxide / tetrahydrofuran; liquid ammonia / 1 h / -35 °C 3: 86 percent / malonic acid / 24 h / 20 °C 4: 91 percent / potassium tert-butoxide / tetrahydrofuran / 2 h / 0 °C 5: 79 percent / oxalic acid dihydrate / H2O; ethanol / 2 h / 20 °C View Scheme

: 63841-74-7
7α-methyl-3,17-dioxoandrost-4-en-19-al

: 5630-53-5
tibolone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 98 percent / magnesium methoxide / tetrahydrofuran; liquid ammonia / 1 h / -35 °C 2: 86 percent / malonic acid / 24 h / 20 °C 3: 91 percent / potassium tert-butoxide / tetrahydrofuran / 2 h / 0 °C 4: 79 percent / oxalic acid dihydrate / H2O; ethanol / 2 h / 20 °C View Scheme

: 10449-00-0
7α-methylestrone 3-methyl ether

: 5630-53-5
tibolone

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: LiAlH4 / tetrahydrofuran 2: Na, tBuOH, liq. NH3 / tetrahydrofuran 3: Al(OiPr)3, cyclohexanone / toluene 4: ethane-1,2-diamine / dimethylsulfoxide; toluene 5: aq. oxalic acid / methanol View Scheme

: 15506-02-2
7α-methyloestradiol-3-methylether

: 5630-53-5
tibolone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Al(OiPr)3, cyclohexanone / toluene 2: ethane-1,2-diamine / dimethylsulfoxide; toluene 3: aq. oxalic acid / methanol View Scheme

: 5210-25-3
3-Methoxy-7α-methyl-17-oxo-Δ2,5(10)-19-norandrostadien

: 5630-53-5
tibolone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ethane-1,2-diamine / dimethylsulfoxide; toluene 2: aq. oxalic acid / methanol View Scheme

: 15506-01-1
3-methoxy-7α-methylestra-1,3,5(10)-trien-17β-ol

: 5630-53-5
tibolone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: Na, tBuOH, liq. NH3 / tetrahydrofuran 2: Al(OiPr)3, cyclohexanone / toluene 3: ethane-1,2-diamine / dimethylsulfoxide; toluene 4: aq. oxalic acid / methanol View Scheme

: 68-22-4
norethisterone

: 5630-53-5
tibolone

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: acetic anhydride; pyridine / 6 h / 20 °C / Industrial scale 2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 0 - 5 °C / Industrial scale 2.2: 3 h / 70 - 75 °C / Industrial scale 3.1: acetic acid / water / Industrial scale 4.1: 3 h / 0 - 5 °C / Industrial scale 5.1: acetyl chloride / 3 h / -10 - 5 °C / Industrial scale 6.1: sulfuric acid / water; acetone / 1 h / 0 - 5 °C / Industrial scale View Scheme

Yield

Multi-step reaction with 6 steps
1.1: acetic anhydride; pyridine / 6 h / 20 °C / Industrial scale
2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 0 - 5 °C / Industrial scale
2.2: 3 h / 70 - 75 °C / Industrial scale
3.1: acetic acid / water / Industrial scale
4.1: 3 h / 0 - 5 °C / Industrial scale
5.1: acetyl chloride / 3 h / -10 - 5 °C / Industrial scale
6.1: sulfuric acid / water; acetone / 1 h / 0 - 5 °C / Industrial scale
View Scheme

: 2205-78-9
3,17-diacetoxy-19-nor-17βH-pregna-3,5-dien-20-yne

: 5630-53-5
tibolone

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 0 - 5 °C / Industrial scale 1.2: 3 h / 70 - 75 °C / Industrial scale 2.1: acetic acid / water / Industrial scale 3.1: 3 h / 0 - 5 °C / Industrial scale 4.1: acetyl chloride / 3 h / -10 - 5 °C / Industrial scale 5.1: sulfuric acid / water; acetone / 1 h / 0 - 5 °C / Industrial scale View Scheme

: 734-32-7
estra-4-ene-3,17-dione

: 5630-53-5
tibolone

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: potassium hydroxide / toluene; tert-butyl alcohol / 0.17 h / 760.05 Torr / Reflux; Industrial scale 1.2: 6 h / Industrial scale 2.1: acetic anhydride; pyridine / 6 h / 20 °C / Industrial scale 3.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 0 - 5 °C / Industrial scale 3.2: 3 h / 70 - 75 °C / Industrial scale 4.1: acetic acid / water / Industrial scale 5.1: 3 h / 0 - 5 °C / Industrial scale 6.1: acetyl chloride / 3 h / -10 - 5 °C / Industrial scale 7.1: sulfuric acid / water; acetone / 1 h / 0 - 5 °C / Industrial scale View Scheme

Yield

Multi-step reaction with 7 steps
1.1: potassium hydroxide / toluene; tert-butyl alcohol / 0.17 h / 760.05 Torr / Reflux; Industrial scale
1.2: 6 h / Industrial scale
2.1: acetic anhydride; pyridine / 6 h / 20 °C / Industrial scale
3.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 0 - 5 °C / Industrial scale
3.2: 3 h / 70 - 75 °C / Industrial scale
4.1: acetic acid / water / Industrial scale
5.1: 3 h / 0 - 5 °C / Industrial scale
6.1: acetyl chloride / 3 h / -10 - 5 °C / Industrial scale
7.1: sulfuric acid / water; acetone / 1 h / 0 - 5 °C / Industrial scale
View Scheme

: C22H27BrO3

: 5630-53-5
tibolone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: acetic acid / water / Industrial scale 2: 3 h / 0 - 5 °C / Industrial scale 3: acetyl chloride / 3 h / -10 - 5 °C / Industrial scale 4: sulfuric acid / water; acetone / 1 h / 0 - 5 °C / Industrial scale View Scheme

: Acetic acid (8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-3-oxo-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

: 5630-53-5
tibolone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 3 h / 0 - 5 °C / Industrial scale 2: acetyl chloride / 3 h / -10 - 5 °C / Industrial scale 3: sulfuric acid / water; acetone / 1 h / 0 - 5 °C / Industrial scale View Scheme

: 6,7-dehydro norethindrone

: 5630-53-5
tibolone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: copper(l) chloride / tetrahydrofuran / -20 °C / Inert atmosphere 2: Pyridine hydrobromide; boron trifluoride diethyl etherate / 40 °C / Inert atmosphere 3: oxalic acid / methanol; water / 25 °C View Scheme
Multi-step reaction with 3 steps 1: copper dichloride / diethyl ether / -30 °C / Inert atmosphere 2: Pyridine hydrobromide; boron trifluoride diethyl etherate / 40 °C / Inert atmosphere 3: oxalic acid / methanol; water / 25 °C View Scheme
Multi-step reaction with 3 steps 1: copper diacetate / tetrahydrofuran; 2-methyltetrahydrofuran / -40 °C / Inert atmosphere 2: Pyridine hydrobromide; boron trifluoride diethyl etherate / 40 °C / Inert atmosphere 3: oxalic acid / methanol; water / 25 °C View Scheme

: 1162-60-3
7α-methyl-17α-ethinyl-17β-hydroxy-4-estren-3-one

: 5630-53-5
tibolone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Pyridine hydrobromide; boron trifluoride diethyl etherate / 40 °C / Inert atmosphere 2: oxalic acid / methanol; water / 25 °C View Scheme

: 5630-53-5
tibolone

: 158932-37-7
17α-ethynyl-7α-methyl-5(10)-estren-3ξ,17β-diol

Conditions

Conditions	Yield
With diisobutylaluminium hydride In toluene at 0℃; for 3h;	80%

: 5630-53-5
tibolone

A: 100239-44-9
3alpha-Hydroxytibolone

B: 100239-45-0
(3β,7α,17α)-17-hydroxy-7-methyl-19-norpregn-5(10)-en-20-yn-3,17-diol

Conditions

Conditions	Yield
With lithium tri(t-butoxy)aluminum hydride In tetrahydrofuran at -70℃; for 2h;	A 70% B n/a
With ethanol; Sacharomyces cerevisiae CBS 3093 In phosphate buffer at 28℃; for 168h; pH=6.0; Title compound not separated from byproducts.;
Stage #1: tibolone With sodium tetrahydroborate In dichloromethane at 0 - 20℃; Stage #2: With acetic acid In dichloromethane at 20℃;	A 400 mg B 300 mg
With sodium tetrahydroborate In dichloromethane at 0 - 20℃; for 5h; Microbiological reaction;

: 5630-53-5
tibolone

: 1162-60-3
7α-methyl-17α-ethinyl-17β-hydroxy-4-estren-3-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In tetrahydrofuran; water for 48h; Reflux;	70%
With hydrogenchloride In methanol
With Fusarium lini NRRL 68751 In water; acetone at 22℃; for 144h; Microbiological reaction; Culture medium; Enzymatic reaction;
With Fusarium lini (ATCC 9593) In acetone for 144h; Microbiological reaction;

: 5630-53-5
tibolone

: 7α-methyl-17α-ethynyl-10β,17β-dihydroxy-19-norandrost-4-en-3-one

Conditions

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate); triphenylphosphine; N,N,N',N'-tetramethylguanidine In tetrahydrofuran at 20℃; for 20h; regioselective reaction;	56%
Multi-step reaction with 2 steps 1: 45 percent / hematoporphyrin, oxygen / pyridine / 1 h / 20 °C / Irradiation 2: 73 percent / triethyl phosphite / ethanol / 1 h / 20 °C View Scheme

: 5630-53-5
tibolone

: 105186-34-3
10β-hydroperoxy-17β-hydroxy-7α-methyl-19-nor-17α-pregn-4-en-20-yn-3-one

Conditions

Conditions	Yield
With oxygen; hematoporphyrin In pyridine at 20℃; for 1h; Irradiation;	45%

: 5630-53-5
tibolone

: 15506-11-3
3-Oxo-7α-methyl-17α-aethinyl-17β-hydroxy-Δ4.9-19-norandrostadien

Conditions

Conditions	Yield
With pyridine; bromine In tetrachloromethane

: 5630-53-5
tibolone

: 100239-44-9
3alpha-Hydroxytibolone

Conditions

Conditions	Yield
With D-glucose; Kluyveromyces lactis CBS 2359 In phosphate buffer at 28℃; for 48h; pH=6.0;
Multi-step reaction with 3 steps 1: 80 percent / DIBAL / toluene / 3 h / 0 °C 2: 0.85 g / Candida antarctica lipase Novozym 435 / toluene / 1 h / 30 °C 3: 95 percent / potassium carbonate / methanol; H2O / 3 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 80 percent / DIBAL / toluene / 3 h / 0 °C 2: 90 percent / pyridine / 3 h / 0 °C 3: 0.285 g / Candida antarctica lipase B Novozym 435; 1-octanol / toluene / 24 h / 30 °C View Scheme

: 5630-53-5
tibolone

: 100239-45-0
(3β,7α,17α)-17-hydroxy-7-methyl-19-norpregn-5(10)-en-20-yn-3,17-diol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / DIBAL / toluene / 3 h / 0 °C 2: 0.24 g / Candida antarctica lipase Novozym 435 / toluene / 1 h / 30 °C View Scheme
Multi-step reaction with 3 steps 1: 70 percent / lithium tri-tert-butoxyaluminum hydride / tetrahydrofuran / 2 h / -70 °C 2: 65 percent / Ph3P; diisopropyl azodicarboxylate / diethyl ether / 20 °C 3: 53 percent / Na2CO3 / methanol; H2O / 4 h / 50 °C View Scheme
With potassium phosphate; recombinant human aldo-keto reductase 1C2; NADPH In methanol at 37℃; pH=7; Kinetics; Reagent/catalyst; Concentration; aq. phosphate buffer; Enzymatic reaction;

: 5630-53-5
tibolone

: 500019-09-0
17α-ethynyl-17β-hydroxy-7α-methyl-5(10)-estren-α3-yl acetate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / DIBAL / toluene / 3 h / 0 °C 2: 0.85 g / Candida antarctica lipase Novozym 435 / toluene / 1 h / 30 °C View Scheme

: 5630-53-5
tibolone

: 17α-ethynyl-17β-hydroxy-7α-methyl-5(10)-estren-β3-yl acetate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / DIBAL / toluene / 3 h / 0 °C 2: 90 percent / pyridine / 3 h / 0 °C 3: 0.135 g / Candida antarctica lipase B Novozym 435; 1-octanol / toluene / 24 h / 30 °C View Scheme

: 5630-53-5
tibolone

: 500019-11-4
17α-ethynyl-17β-hydroxy-7α-methyl-5(10)-estren-ξ3-yl acetate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / DIBAL / toluene / 3 h / 0 °C 2: 90 percent / pyridine / 3 h / 0 °C View Scheme

: 5630-53-5
tibolone

: Benzoic acid (3S,7R,8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-7,13-dimethyl-2,3,4,6,7,8,9,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / lithium tri-tert-butoxyaluminum hydride / tetrahydrofuran / 2 h / -70 °C 2: 65 percent / Ph3P; diisopropyl azodicarboxylate / diethyl ether / 20 °C View Scheme

: 5630-53-5
tibolone

: 15505-74-5
7α-Methyl-3-oxo-17α-aethinyl-17β-hydroxy-Δ5.(10).9(11)-19-norandrostadien

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Br2, Py / CCl4 2: (i) pyrrolidine, MeOH, (ii) AcOH View Scheme

: 5630-53-5
tibolone

: 3-Oxo-7α-methyl-17α-ethinyl-17β-hydroxy-Δ4.9.11-19-norandrostatrien

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Br2, Py / CCl4 2: (i) pyrrolidine, MeOH, (ii) AcOH 3: (i) MCPBA, CH2Cl2, (ii) Al2O3, (iii) BF3-Et2O View Scheme

: 5630-53-5
tibolone

: [7α,17α]-17-hydroxy-7-methyl-19-norpregn-4(5)-en-20-yn-3-one

Conditions

Conditions	Yield
With hydrogenchloride In water
With hydrogenchloride In water; acetone for 4h; Reflux;

Tibolone Specification

1. Introduction of Tibolone

The Tibolone belongs to the product categories of Active Pharmaceutical Ingredients; Hormone; Acetylenes; Biochemistry; Functionalized Acetylenes; Hydroxyketosteroids; Steroids; Intermediates & Fine Chemicals; Pharmaceuticals. Its IUPAC name is called 17-ethynyl-17-hydroxy-7,13-dimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one. This chemical's classification codes are Anabolic; Anabolic Agents; Androgen Antagonists; Antihypertensive Agents; Antineoplastic Agents; Antineoplastic agents, hormonal; Cardiovascular Agents; Estrogen Receptor Modulators; Hormone Antagonists; Hormones; Hormones, Hormone Substitutes, and Hormone Antagonists; Menopausal symptoms suppressant.

2. Properties of Tibolone

Physical properties of Tibolone: (1)ACD/LogP: 4.03; (2)#H bond acceptors: 2; (3)#H bond donors: 1; (4)#Freely Rotating Bonds: 1; (5)Index of Refraction: 1.57; (6)Molar Refractivity: 89.95 cm³; (7)Molar Volume: 274.1 cm³; (8)Surface Tension: 47.4 dyne/cm; (9)Density: 1.13 g/cm³; (10)Flash Point: 190.6 °C; (11)Enthalpy of Vaporization: 81.43 kJ/mol; (12)Boiling Point: 447.4 °C at 760 mmHg; (13)Vapour Pressure: 6.96E-10 mmHg at 25°C.

3. Structure Descriptors of Tibolone

You could convert the following datas into the molecular structure:
(1)Canonical SMILES: CC1CC2=C(CCC(=O)C2)C3C1C4CCC(C4(CC3)C)(C#C)O
(2)InChI: InChI=1S/C21H28O2/c1-4-21(23)10-8-18-19-13(2)11-14-12-15(22)5-6-16(14)17(19)7-9-20(18,21)3/h1,13,17-19,23H,5-12H2,2-3H3
(3)InChIKey: WZDGZWOAQTVYBX-UHFFFAOYSA-N

4. Safety Information of Tibolone

When you are using this chemical, please be cautious about it as the following:
This chemical may present an immediate or delayed danger to one or more components of the environment. It is toxic to aquatic organisms which may cause long-term adverse effects in the aquatic environment. In addition, you should not breathe its dust. You must avoid contacting it with skin and eyes. What's more, you must avoid releasing it to the environment.

5. Preparation of Tibolone

Preparation: this chemical can be prepared by 7α-methyl-10-formaldehyde-based progesterone-4-ene-3,17-dione.

Tibolone is a synthetic steroid hormone drug, which is fairly non-selective in its binding profile, acting as an agonist at all five of the Type I steroid hormone receptors. It is used mainly for treatment of endometriosis, as well as hormone replacement therapy in post-menopausal women.

Product Name

Tibolone

Synthetic route

Tibolone Specification

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