Name: 17-Hydroxy-7-alpha-mercapto-3-oxo-17-alpha-pregn-4-ene-21-carboxylic acid-gamma-lactone-7-acetate
SKU: 52-01-7

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Basic Information

Molecular Structure:
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

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:	T, Xn, Xi
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

Conditions	Yield
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

Conditions	Yield
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%

...Expand

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

Conditions	Yield
In toluene

...Expand

: 976-70-5
3-oxopregn-4-ene-21,17α-carbolactone

: 52-01-7
SPIRONOLACTONE

Conditions

Conditions	Yield
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

Yield

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

Yield

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Yield

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

Raw Materials

976-70-5

434-03-7

976-71-6

507-09-5

Downstream Products

38753-77-4

976-71-6

Total:183 Page 1 of 5 1 2 3 4 5 Next>>

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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.

52-01-7

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Specification