Oxandrolone supplier | CasNO.53-39-4

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Name
Oxandrolone
EINECS 200-172-9
CAS No. 53-39-4
Article Data9
CAS DataBase
Density 1.105 g/cm³
Solubility very slightly soluble in water
Melting Point 235-238 °C
Formula C₁₉H₃₀O₃
Boiling Point 444.4 °C at 760mmHg
Molecular Weight 306.445
Flash Point 179.1 °C
Transport Information
Appearance White crystalline powder
Safety 22-36/37/39-45
Risk Codes 60-63-20/21/22
Molecular Structure
Hazard Symbols T
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)-;
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

: 74252-42-9, 76333-34-1
2α-bromo-17β-hydroxy-17α-methyl-5α-androstan-3-one

: 53-39-4
oxandrolone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: lithium carbonate; lithium bromide / N,N-dimethyl-formamide / 3 h / 110 - 115 °C / Inert atmosphere 2.1: ozone / methanol / 6 h / -40 - -30 °C / Inert atmosphere; Large scale 3.1: sodium hydroxide / ethanol; water / 8 - 9 °C / Inert atmosphere 3.2: 1 h / 5 - 7 °C 3.3: 8.75 h / 1 - 9 °C View Scheme

: 18167-94-7, 35937-38-3, 132830-76-3, 65-04-3
5α-17β-hydroxy-17α-methyl-Δ1-androsten-3-one

: 53-39-4
oxandrolone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: ozone / methanol / 6 h / -40 - -30 °C / Inert atmosphere; Large scale 2.1: sodium hydroxide / ethanol; water / 8 - 9 °C / Inert atmosphere 2.2: 1 h / 5 - 7 °C 2.3: 8.75 h / 1 - 9 °C View Scheme

: 53-39-4
oxandrolone

: 142793-21-3
17,17-dimethyl-18-nor-2-oxa-5α-androst-13(14)-en-3-one

Conditions

Conditions	Yield
With hydrogenchloride for 0.25h; Ambient temperature;	73%

: 53-39-4
oxandrolone

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

Conditions

Conditions	Yield
With water; sodium hydroxide In methanol at 20℃; for 0.25h; Inert atmosphere;	52%

: 53-39-4
oxandrolone

A: 1207298-36-9
6α-hydroxyoxandrolone

B: 1207298-35-8
11α-hydroxyoxandrolone

C: 1207298-37-0
9α-hydroxyoxandrolone

Conditions

Conditions	Yield
With potassium dihydrogenphosphate; D-glucose; sodium chloride; peptone; yeast extract In water; acetone at 28℃; for 240h;	A 5% B 25% C 8%

...Expand

: 110-86-1
pyridine

: 53-39-4
oxandrolone

: 143601-31-4
oxandrolone 17β-sulfate pyridinium salt

Conditions

Conditions	Yield
With chlorosulfonic acid 1.) -5 deg C, 2.) RT, 3 h; Yield given. Multistep reaction;

: 53-39-4
oxandrolone

: 143601-30-3
Sulfuric acid mono-((5S,8R,9S,10S,13S,14S,17S)-10,13,17-trimethyl-3-oxo-hexadecahydro-2-oxa-cyclopenta[a]phenanthren-17-yl) ester

Conditions

Conditions	Yield
With sulfur trioxide pyridine complex In N,N-dimethyl-formamide for 2h; Ambient temperature;

: 53-39-4
oxandrolone

: 26624-15-7
17α-hydroxy-17β-methyl-2-oxa-5α-androstan-3-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfur trioxide pyridine complex / dimethylformamide / 2 h / Ambient temperature 2: H2O / 12 h View Scheme

: 53-39-4
oxandrolone

: 136693-21-5
(5S,8R,9S,10S,13S,14S,17R)-10,13,17-Trimethyl-17-trimethylsilanyloxy-tetradecahydro-2-oxa-cyclopenta[a]phenanthren-3-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfur trioxide pyridine complex / dimethylformamide / 2 h / Ambient temperature 2: H2O / 12 h 3: trimethylsilylimidazole / 0.17 h / 60 °C View Scheme

: 53-39-4
oxandrolone

: 17-epioxandrolone,TMS

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfur trioxide pyridine complex / dimethylformamide / 2 h / Ambient temperature 2: H2O / 12 h 3: trimethylsilylimidazole / 0.17 h / 60 °C 4: trimethyliodosilane / 0.25 h / 60 °C View Scheme

: 107-30-2
chloromethyl methyl ether

: 53-39-4
oxandrolone

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

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 60℃; Inert atmosphere;

: 24589-78-4
N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide

: 53-39-4
oxandrolone

: 136693-20-4
C22H38O3Si

Conditions

Conditions	Yield
With ammonium iodide; 2-hydroxyethanethiol at 60℃; for 0.333333h;

: 53-39-4
oxandrolone

A: 5α,11β,17β-trihydroxy-17α-methyl-2-oxa-androstan-3-one

B: 17β-hydroxy-17α-methyl-2-oxa-5α-androstan-3,11-dione

C: 11β,17β-dihydroxy-17α-methyl-2-oxa-5α-androstan-3-one

D: 11β,17β-dihydroxy-17α-(hydroxymethyl)-2-oxa-5α-androstan-3-one

Conditions

Conditions	Yield
With culture medium of Macrophomina phaseolina In methanol at 26℃; for 456h; Microbiological reaction;	A 10 mg B 15 mg C 30 mg D 25 mg

...Expand

: 53-39-4
oxandrolone

: 12β,17β-dihydroxy-17α-methyl-2-oxa-5α-androstan-3-one

Conditions

Conditions	Yield
With culture of Cunninghamella blakesleeana In methanol at 26℃; for 432h; Microbiological reaction;	8 mg

: 53-39-4
oxandrolone

A: 17-methylene-2-oxaandrost-13-en-3-one

B: C19H28O2

Conditions

Conditions	Yield
With pyridine; trichlorophosphate at 50℃; for 1.5h;

: 53-39-4
oxandrolone

A: (5α,13β)-spiro(2-oxaandrost-17β,2'-oxirane)-3-one

B: (5α,13β)-spiro(2-oxaandrost-17α,2'-oxirane)-3-one

C: C19H28O3

Conditions

Conditions	Yield
Stage #1: oxandrolone With pyridine; trichlorophosphate at 50℃; for 1.5h; Stage #2: With 3-chloro-benzenecarboperoxoic acid In aq. phosphate buffer; chloroform at 20℃; for 3h;	A 56 mg B n/a C n/a

...Expand

: 53-39-4
oxandrolone

A: 17α-hydroxymethyl-17β-methyl-18-nor-2-oxaandrost-13-en-3-one

B: C19H28O3

Conditions

Conditions	Yield
Stage #1: oxandrolone With pyridine; trichlorophosphate at 50℃; for 1.5h; Stage #2: With 3-chloro-benzenecarboperoxoic acid In aq. phosphate buffer; chloroform at 20℃; for 3h; Stage #3: With acetic acid at 20℃; for 24h;	A 145 mg B n/a

Oxandrolone 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.

Product Name

Oxandrolone

Synthetic route

Oxandrolone Specification

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