CAS No.53-39-4,Oxandrolone Suppliers

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Basic Information

Molecular Structure:
CAS No.:	53-39-4
Name:	Oxandrolone
Article Data:	9
Cas Database

Formula:	C₁₉H₃₀O₃
Molecular Weight:	306.445
Synonyms:	2-Oxa-5a-androstan-3-one, 17b-hydroxy-17-methyl- (7CI,8CI);2-Oxaandrostan-3-one, 17-hydroxy-17-methyl-, (5a,17b)-;17-Methyl-2-oxa-5a-androstan-17b-ol-3-one;17b-Hydroxy-17-methyl-2-oxa-5a-androstan-3-one;17b-Hydroxy-17a-methyl-2-oxa-5a-androstan-3-one;8075CB;Anavar;Lonavar;NSC 67068;Oxandren;Oxandrin;Protivar;Provitar;SC11585;Vasorome;Cyclopenta[5,6]naphtho[1,2-c]pyran-2(1H)-one,tetradecahydro-7-hydroxy-4a,6a,7-trimethyl-, (4aS,4bS,6aS,7S,9aS,9bR,11aS)-;
EINECS:	200-172-9
Density:	1.105 g/cm³
Melting Point:	235-238 °C
Boiling Point:	444.4 °C at 760mmHg
Flash Point:	179.1 °C
Solubility:	very slightly soluble in water
Appearance:	White crystalline powder
Hazard Symbols:	T
Risk Codes:	60-63-20/21/22
Safety:	22-36/37/39-45
PSA:	46.53000
LogP:	3.54310

Synthetic route

: 17-β-hydroxy-17-α-methyl-1-oxo-1,2-seco-A-nor-5-α-androstan-2-oic acid

: 53-39-4
oxandrolone

Conditions

Conditions	Yield
Stage #1: 17-β-hydroxy-17-α-methyl-1-oxo-1,2-seco-A-nor-5-α-androstan-2-oic acid With sodium hydroxide In ethanol; water at 8 - 9℃; Inert atmosphere; Stage #2: With sodium tetrahydroborate In ethanol; water at 5 - 7℃; for 1h; Stage #3: With hydrogenchloride In ethanol; water at 1 - 9℃; for 8.75h;	94%

: 1219000-90-4
(4aS,4bS,6aS,7S,9aS,9bR,11aS)-7-(methoxymethoxy)-4a,6a,7-trimethyltetradeca-hydroindeno[4,5-h]isochromen-2(1H)-one

: 53-39-4
oxandrolone

Conditions

Conditions	Yield
With 1-thiopropane; zinc dibromide In dichloromethane at 20℃; for 0.116667h; Inert atmosphere;	91%

: ((3S,3aS,5aS,6S,7S,9aR,9bS)-6-Acetoxymethyl-3-hydroxy-3,3a,6-trimethyl-dodecahydro-cyclopenta[a]naphthalen-7-yl)-acetic acid

: 53-39-4
oxandrolone

Conditions

Conditions	Yield
With potassium hydroxide In methanol; water at 50℃; for 3h;	0.06 g

: 7745-45-1
17α-methyl-1,3-seco-2-nor-5α-androstane-1,3,17α-triol

: 53-39-4
oxandrolone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 90 percent / pyridine / 20 °C 2: 85 percent / Candida antarctica B lipase / ethanol / 3 h / 30 °C 3: Jones reagent / acetone 4: 0.06 g / KOH / methanol; H2O / 3 h / 50 °C View Scheme

: 624740-15-4
17β-hydroxy-17α-methyl-1,3-seco-2-nor-5α-androstane-1,3-diacid 1,3-dimethylester

: 53-39-4
oxandrolone

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 20 °C 2: 90 percent / pyridine / 20 °C 3: 85 percent / Candida antarctica B lipase / ethanol / 3 h / 30 °C 4: Jones reagent / acetone 5: 0.06 g / KOH / methanol; H2O / 3 h / 50 °C View Scheme

: 141691-35-2
(3S,3aS,5aS,6S,7S,9aS,9bS)-7-Carboxymethyl-3-hydroxy-3,3a,6-trimethyl-dodecahydro-cyclopenta[a]naphthalene-6-carboxylic acid

: 53-39-4
oxandrolone

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: methanol; diethyl ether 2: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 20 °C 3: 90 percent / pyridine / 20 °C 4: 85 percent / Candida antarctica B lipase / ethanol / 3 h / 30 °C 5: Jones reagent / acetone 6: 0.06 g / KOH / methanol; H2O / 3 h / 50 °C View Scheme

: 624740-17-6
Acetic acid (3S,3aS,5aS,6S,7S,9aR,9bS)-3-hydroxy-7-(2-hydroxy-ethyl)-3,3a,6-trimethyl-dodecahydro-cyclopenta[a]naphthalen-6-ylmethyl ester

: 53-39-4
oxandrolone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Jones reagent / acetone 2: 0.06 g / KOH / methanol; H2O / 3 h / 50 °C View Scheme

: 7745-12-2
17α-methyl-1,3-seco-2-nor-5α-androstane-1,3,17α-triol 1,3-diacetate

: 53-39-4
oxandrolone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 85 percent / Candida antarctica B lipase / ethanol / 3 h / 30 °C 2: Jones reagent / acetone 3: 0.06 g / KOH / methanol; H2O / 3 h / 50 °C View Scheme

: 313047-21-1
17β-hydroxy-17α-methyl-2-oxa-5α-androstane-1,3-dione

: 53-39-4
oxandrolone

Conditions

Conditions	Yield
With sodium borohydrid; sulfuric acid In water; N,N-dimethyl-formamide	6.1 g (75.2%)

: 521-11-9
mestanolone

: 53-39-4
oxandrolone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: pyridinium hydrobromide perbromide / ethanol; water / 5.25 h / 24 - 27 °C / Inert atmosphere; Large scale 2.1: lithium carbonate; lithium bromide / N,N-dimethyl-formamide / 3 h / 110 - 115 °C / Inert atmosphere 3.1: ozone / methanol / 6 h / -40 - -30 °C / Inert atmosphere; Large scale 4.1: sodium hydroxide / ethanol; water / 8 - 9 °C / Inert atmosphere 4.2: 1 h / 5 - 7 °C 4.3: 8.75 h / 1 - 9 °C View Scheme

Yield

Multi-step reaction with 4 steps
1.1: pyridinium hydrobromide perbromide / ethanol; water / 5.25 h / 24 - 27 °C / Inert atmosphere; Large scale
2.1: lithium carbonate; lithium bromide / N,N-dimethyl-formamide / 3 h / 110 - 115 °C / Inert atmosphere
3.1: ozone / methanol / 6 h / -40 - -30 °C / Inert atmosphere; Large scale
4.1: sodium hydroxide / ethanol; water / 8 - 9 °C / Inert atmosphere
4.2: 1 h / 5 - 7 °C
4.3: 8.75 h / 1 - 9 °C
View Scheme

Raw Materials

521-11-9

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Specification

Oxandrolone is one kind of white or almost white crystalline powder. The IUPAC name of this chemical is (1S,3aS,3bR,5aS,9aS,9bS,11aS)-1-hydroxy-1,9a,11a-trimethyl-2,3,3a,3b,4,5,5a,6,9,9b,10,11-dodecahydroindeno[4,5-h]isochromen-7-one. The product's categories are miscellaneous; biochemistry; steroids. Additionally, Oxandrolone is toxic and flammable. This chemical is odorless and white crystalline powder which is soluble in chloroform, slightly soluble in ethanol, acetone, ether, and very slightly soluble in water. Besides, the Classification Code of Oxandrolone is Anabolic Agents; Androgen; Androgens; Hormone; Hormones; Hormones, Hormone Substitutes, and Hormone Antagonists; Reproductive Effect. The Oxandrolone is male hormone with the major role protein assimilation. It is used in the treatment of high cholesterol and triglyceride disorders. It will produce irritative smoke when buring. So the storage environment should be ventilate, low-temperature and dry. Furthermore, Oxandrolone can be obtained by 5-androstane-1-en-3-17-dione or 17β-Hydroxy-17-α-methyl derivatives.

Physical properties about Oxandrolone are:
(1)ACD/LogP: 3.33; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.33; (4)ACD/LogD (pH 7.4): 3.33; (5)ACD/BCF (pH 5.5): 199.84; (6)ACD/BCF (pH 7.4): 199.84; (7)ACD/KOC (pH 5.5): 1543.23; (8)ACD/KOC (pH 7.4): 1543.23; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.526; (13)Molar Refractivity: 85.1 cm³; (14)Molar Volume: 277 cm³; (15)Polarizability: 33.73×10^-24 cm³; (16)Surface Tension: 39.8 dyne/cm; (17)Enthalpy of Vaporization: 81.03 kJ/mol; (18)Vapour Pressure: 9.19E-10 mmHg at 25°C; (19)Tautomer Count: 2; (20)Exact Mass: 306.219495; (21)MonoIsotopic Mass: 306.219495; (22)Topological Polar Surface Area: 46.5; (23)Heavy Atom Count: 22; (24)Complexity: 503.

People can use the following data to convert to the molecule structure.
(1)SMILES:O=C3OC[C@@]2([C@H]1CC[C@@]4(C)[C@H]([C@@H]1CC[C@H]2C3)CC[C@@]4(O)C)C;
(2)Std. InChI:InChI=1S/C19H30O3/c1-17-11-22-16(20)10-12(17)4-5-13-14(17)6-8-18(2)15(13)7-9-19(18,3)21/h12-15,21H,4-11H2,1-3H3/t12-,13+,14-,15-,17-,18-,19-/m0/s1;
(3)Std. InChIKey:QSLJIVKCVHQPLV-PEMPUTJUSA-N.

The following are the toxicity of Oxandrolone:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
man	TDLo	oral	2400ug/kg/2W- (2.4mg/kg)	BEHAVIORAL: EUPHORIA BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: IRRITABILITY	Journal of Clinical Psychiatry. Vol. 46, Pg. 354, 1985.
mouse	LD50	intraperitoneal	922mg/kg (922mg/kg)	SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 65, Pg. 418, 1969.
mouse	LD50	oral	1832mg/kg (1832mg/kg)	SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 65, Pg. 418, 1969.
mouse	LD50	subcutaneous	> 11gm/kg (11000mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 65, Pg. 418, 1969.
rabbit	LD50	oral	> 5gm/kg (5000mg/kg)		Drugs in Japan Vol. 6, Pg. 149, 1982.
rat	LD50	intraperitoneal	4893mg/kg (4893mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: TREMOR	Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 65, Pg. 418, 1969.
rat	LD50	oral	> 10gm/kg (10000mg/kg)		Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 65, Pg. 418, 1969.
rat	LD50	subcutaneous	> 10gm/kg (10000mg/kg)		Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 65, Pg. 418, 1969.

Uses of Oxandrolone:
Oxandrolone is a synthetic hormone with anabolic and androgenic properties. It can be used to promote muscle growth and combat involuntary weight loss. It has also been used to treat cases of osteoporosis. Besides, It is a synthetic anabolic steroid derivative of dihydrotestosterone with an oxygen atom replacing the 2 carbon and methylation in the 17 position.

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