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52-01-7

Basic Information
CAS No.: 52-01-7
Name: 17-Hydroxy-7-alpha-mercapto-3-oxo-17-alpha-pregn-4-ene-21-carboxylic acid-gamma-lactone-7-acetate
Article Data: 15
Molecular Structure:
Molecular Structure of 52-01-7 (17-Hydroxy-7-alpha-mercapto-3-oxo-17-alpha-pregn-4-ene-21-carboxylic acid-gamma-lactone-7-acetate)
Formula: C24H32O4S
Molecular Weight: 416.582
Synonyms: Alderon;3-(3-Keto-7.alpha.-acetylthio-17.beta.-hydroxy-4-androsten-17.alph a.-yl)propionic acid lactone;Uractone;Spiro(17H-cyclopenta(a)phenauthrene-17,2-(3H)-furan);Xenalon;Pregn-4-ene-21-carboxylic acid,7-(acetylthio)-17-hydroxy-3-oxo-,?- lactone,(7R,17R)-;Aldactone;17.alpha.-Pregn-4-ene-21-carboxylic acid, 17-hydroxy-7.alpha.-mercapto-3-oxo-, .gamma.-lactone, acetate;Euteberol;Prestwick_449;Pregn-4-ene-21-carboxylic acid, 7-(acetylthio)-17-hydroxy-3-oxo-, gamma-lactone, (7alpha,17alpha)-;Spironolactone A;Urusonin;Verospirone;SC 9420;SC 15983;Spiro(17H-cyclopenta(a)phenanthrene-17,2(5H)-furan), pregn-4-ene-21-carboxylic acid deriv.;Spiro-Tablinen;Spirolang;Spironolactone [BAN:INN:JAN];7-alpha-Acetylthio-3-oxo-17-alpha-pregn-4-ene-21,17-beta-carbolactone;7-alpha-(acetylthio)-17-alpha-hydroxy-3-oxopregn-4-ene-21-carboxylic acid, gamma-lactone (9CI);496916-40-6;Spironolactonum [INN-Latin];Aldactone A;Aldactazide (TN);Spiroctan;3-(3-Oxo-7-alpha-acetylthio-17-beta-hydroxyandrost-4-en-17-beta-yl)propionic acid lactone;7-(Acetylthio)-17-hydroxy-3-oxopregn-4-ene-21-carboxylic acid gamma-lactone;Pregn-4-ene-21-carboxylic acid, 7-(acetylthio)-17-hydroxy-3-oxo-, g-lactone, (7a,17a)-;Verospiron;
EINECS: 200-133-6
Density: 1.24 g/cm3
Melting Point: 207-208 °C(lit.)
Boiling Point: 597 °C at 760 mmHg
Flash Point: 302.3 °C
Solubility: practically insoluble in water
Appearance: White to Off White Solid
Hazard Symbols: ToxicT, HarmfulXn, IrritantXi
Risk Codes: 60-40-36/37/38
Safety: 53-22-36/37/39-45-36-26
PSA: 85.74000
LogP: 4.85230
Synthetic route
976-71-6

canrenone

507-09-5

thioacetic acid

52-01-7

SPIRONOLACTONE

Conditions
ConditionsYield
Stage #1: tiolacetic acid With trifluoromethylsulfonic anhydride In tetrahydrofuran
Stage #2: canrenone In tetrahydrofuran at 20℃; for 1h;
76%
With trimethylsilyl trifluoromethanesulfonate In tetrahydrofuran at 20℃; for 3h;60%
In water at 20℃; for 2h; Michael addition;
976-71-6

canrenone

507-09-5

thioacetic acid

A

33784-05-3

β-spironolactone

B

52-01-7

SPIRONOLACTONE

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In tetrahydrofuran for 1h; Ambient temperature; Yields of byproduct given;A n/a
B 64%
With trimethylsilyl trifluoromethanesulfonate In tetrahydrofuran for 1h; Ambient temperature; Yield given;A n/a
B 64%
17α-(2-carboxyethyl-17β-hydroxyandrosta-4,6-dien-3-one lactone

17α-(2-carboxyethyl-17β-hydroxyandrosta-4,6-dien-3-one lactone

976-71-6

canrenone

507-09-5

thioacetic acid

52-01-7

SPIRONOLACTONE

Conditions
ConditionsYield
In toluene
976-70-5

3-oxopregn-4-ene-21,17α-carbolactone

52-01-7

SPIRONOLACTONE

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / p-chloranil / 2-methyl-propan-2-ol / Heating
2: 64 percent / TMSOTf / tetrahydrofuran / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: tetrachloro-<1,4>benzoquinone; xylene; toluene-4-sulfonic acid-monohydrate
View Scheme
434-03-7

levonorgestrel

52-01-7

SPIRONOLACTONE

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 98 percent / trimethyl orthoformate, p-toluenesulfonic acid / methanol / 3 h / 50 °C
2: H2, triphenylphosphine, rhodium acetate dimer / ethyl acetate / 20 h / 80 °C / 9000.7 Torr
3: 100 percent / N-methylmorpholine N-oxide (NMO), RuCl2(Ph3P)3 / dimethylformamide / 0.17 h
4: 97 percent / 6 N HCl / tetrahydrofuran / 0.5 h
5: 70 percent / p-chloranil / 2-methyl-propan-2-ol / Heating
6: 64 percent / TMSOTf / tetrahydrofuran / 1 h / Ambient temperature
View Scheme
50407-76-6

17α-ethynyl-17β-hydroxy-5-androsten-3-one ethylene ketal

52-01-7

SPIRONOLACTONE

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: H2, triphenylphosphine, rhodium acetate dimer / ethyl acetate / 20 h / 80 °C / 9000.7 Torr
2: 100 percent / N-methylmorpholine N-oxide (NMO), RuCl2(Ph3P)3 / dimethylformamide / 0.17 h
3: 97 percent / 6 N HCl / tetrahydrofuran / 0.5 h
4: 70 percent / p-chloranil / 2-methyl-propan-2-ol / Heating
5: 64 percent / TMSOTf / tetrahydrofuran / 1 h / Ambient temperature
View Scheme
121936-43-4

5'-hydroxyspiro-5-en-3-one

52-01-7

SPIRONOLACTONE

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 100 percent / N-methylmorpholine N-oxide (NMO), RuCl2(Ph3P)3 / dimethylformamide / 0.17 h
2: 97 percent / 6 N HCl / tetrahydrofuran / 0.5 h
3: 70 percent / p-chloranil / 2-methyl-propan-2-ol / Heating
4: 64 percent / TMSOTf / tetrahydrofuran / 1 h / Ambient temperature
View Scheme
75219-50-0

C24H34O4

52-01-7

SPIRONOLACTONE

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 97 percent / 6 N HCl / tetrahydrofuran / 0.5 h
2: 70 percent / p-chloranil / 2-methyl-propan-2-ol / Heating
3: 64 percent / TMSOTf / tetrahydrofuran / 1 h / Ambient temperature
View Scheme
972-46-3

3-ethoxyandrosta-3,5-dien-17-one

52-01-7

SPIRONOLACTONE

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: lithium bromide; C30H31Cl3N3(1+)*BF4(1-); triethylamine / 1,2-dichloro-ethane / 5 h / 20 °C / Inert atmosphere; Sealed tube
2.1: chloranil / 1,2-dichloro-ethane; methanol; water / 1 h / 20 °C
3.1: trifluoromethylsulfonic anhydride / tetrahydrofuran
3.2: 1 h / 20 °C
View Scheme
53-43-0

dehydroepiandrosterone

52-01-7

SPIRONOLACTONE

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: iodine; mercury dichloride; magnesium / diethyl ether / 0.5 h / 40 °C
1.2: 2.5 h / 0 - 20 °C
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C
2.2: 2 h / 0 - 20 °C
2.3: 1 h / 0 - 20 °C
3.1: Dess-Martin periodane / dichloromethane / 4 h / 0 - 20 °C
4.1: chloranil / tert-butyl alcohol / 3 h / 80 °C
5.1: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 3 h / 20 °C
View Scheme
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976-71-6
38753-77-4
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Specification

 The Spironolactone, with the cas registry number 52-01-7, has the IUPAC name of S-[(7R,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-3,5'-dioxospiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-7-yl] ethanethioate. This is a kind of white to off white solid, and is practically insoluble. Its product categories are including Active Pharmaceutical Ingredients; Biochemistry; Steroids; Steroids (Others); Intermediates & Fine Chemicals; Pharmaceuticals; API's. As to its usage, it is a kind of diuretic and also used as an antiandrogen.

The physical properties of this chemical are as follows: (1)ACD/LogP: 3.12; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.12; (4)ACD/LogD (pH 7.4): 3.12; (5)ACD/BCF (pH 5.5): 139.34; (6)ACD/BCF (pH 7.4): 139.34; (7)ACD/KOC (pH 5.5): 1192.14; (8)ACD/KOC (pH 7.4): 1192.14; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 85.74; (13)Index of Refraction: 1.585; (14)Molar Refractivity: 112.68 cm3; (15)Molar Volume: 335.7 cm3; (16)Polarizability: 44.67 ×10-24 cm3; (17)Surface Tension: 50.8 dyne/cm; (18)Density: 1.24 g/cm3; (19)Flash Point: 302.3 °C; (20)Enthalpy of Vaporization: 88.93 kJ/mol; (21)Boiling Point: 597 °C at 760 mmHg; (22)Vapour Pressure: 3.24E-14 mmHg at 25°C; (23)Exact Mass: 416.20213; (24)MonoIsotopic Mass: 416.20213; (25)Topological Polar Surface Area: 85.7; (26)Heavy Atom Count: 29; (27)Formal Charge: 0; (28)Complexity: 818.

When you are dealing with this chemical, you should be very cautious. For being a kind of irritant chemical to eyes, respiratory system and skin, it may cause inflammation to the skin or other mucous membranes. Then it is harmful which may cause damage to health. What's more, it is even toxic which could at low levels cause damage to health. This chemical may have impair fertility and may have limited evidence of a carcinogenic effect.

Therefore, you should take the following instructions to protect yourself. Wear suitable protective clothing, gloves and eye/face protection and avoid exposure - obtain special instructions before use. If in case of accident or if you feel unwell seek medical advice immediately (show the label where possible), and if in case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Then do remember not breathe dust. When store it, keep in a dry, cool and well-ventilated place, away from the food raw material.

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: CC(=O)SC1CC2=CC(=O)CCC2(C3C1C4CCC5(C4(CC3)C)CCC(=O)O5)C
(2)Isomeric SMILES: CC(=O)S[C@@H]1CC2=CC(=O)CC[C@@]2([C@@H]3[C@@H]1[C@@H]4CC[C@]5([C@]4(CC3)C)CCC(=O)O5)C
(3)InChI: InChI=1S/C24H32O4S/c1-14(25)29-19-13-15-12-16(26)4-8-22(15,2)17-5-9-23(3)18(21(17)19)6-10-24(23)11-7-20(27)28-24/h12,17-19,21H,4-11,13H2,1-3H3/t17-,18-,19+,21+,22-,23-,24+/m0/s1
(4)InChIKey: LXMSZDCAJNLERA-ZHYRCANASA-N 

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo oral 5600mg/kg (5600mg/kg) KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED Journal of Laboratory and Clinical Medicine. Vol. 80, Pg. 224, 1972.
 
man TDLo oral 5714ug/kg/4D- (5.714mg/kg) LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)"

BLOOD: AGRANULOCYTOSIS

BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED)
Drug Intelligence and Clinical Pharmacy. Vol. 21, Pg. 974, 1987.
 
man TDLo oral 7500ug/kg/3W- (7.5mg/kg) BLOOD: AGRANULOCYTOSIS Australian and New Zealand Journal of Medicine. Vol. 30, Pg. 515, 2000.
 
man TDLo oral 7500ug/kg/3W- (7.5mg/kg) BLOOD: AGRANULOCYTOSIS

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE
Australian and New Zealand Journal of Medicine. Vol. 30, Pg. 515, 2000.
 
mouse LD50 intraperitoneal 260mg/kg (260mg/kg)   Drugs in Japan Vol. 6, Pg. 381, 1982.
mouse LD50 intravenous 260mg/kg (260mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
mouse LD50 oral > 1gm/kg (1000mg/kg)   Journal of Environmental Pathology and Toxicology. Vol. 1(5), Pg. 641, 1978.
rabbit LD50 intraperitoneal 866mg/kg (866mg/kg)   Journal of Environmental Pathology and Toxicology. Vol. 1(5), Pg. 641, 1978.
rabbit LD50 oral > 1gm/kg (1000mg/kg)   Journal of Environmental Pathology and Toxicology. Vol. 1(5), Pg. 641, 1978.
rat LD50 intraperitoneal 277mg/kg (277mg/kg)   Drugs in Japan Vol. 6, Pg. 381, 1982.
rat LD50 oral > 1gm/kg (1000mg/kg)   Drugs in Japan Vol. 6, Pg. 381, 1982.
women TDLo oral 70mg/kg/5W-I (70mg/kg) BLOOD: AGRANULOCYTOSIS British Medical Journal. Vol. 289, Pg. 731, 1984.
women TDLo oral 122mg/kg/61D- (122mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" New Zealand Medical Journal. Vol. 83, Pg. 147, 1976.