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53-39-4

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Basic Information
CAS No.: 53-39-4
Name: Oxandrolone
Molecular Structure:
Molecular Structure of 53-39-4 (Oxandrolone)
Formula: C19H30O3
Molecular Weight: 306.49
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
Transport Information:
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With sodium borohydrid; sulfuric acid In water; N,N-dimethyl-formamide6.1 g (75.2%)
521-11-9

mestanolone

53-39-4

oxandrolone

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With potassium dihydrogenphosphate; D-glucose; sodium chloride; peptone; yeast extract In water; acetone at 28℃; for 240h;A 5%
B 25%
C 8%
110-86-1

pyridine

53-39-4

oxandrolone

143601-31-4

oxandrolone 17β-sulfate pyridinium salt

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
53-39-4

oxandrolone

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

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
53-39-4

oxandrolone

A

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

B

C19H28O3

Conditions
ConditionsYield
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
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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