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Oxandrolone
Cas No: 53-39-4
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Steroid Muscle Building Tablets Anavar CAS 53-39-4 Oxandrolone Powder
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53-39-4 Usage

Description

Oxandrolone is a synthetic anabolic-androgenic steroid. It is a 17 alpha-methylated version of dihydrotestosterone (DHT). It can be used for the treatment of many kinds of disorders such as idiopathic short stature, body mass loss due to catabolic illness, severe burns, trauma and hereditary angioedema as well as turner syndrome. Oxandrolone is especially effective in the treatment of severe burns without causing obvious side effects. It acts as an agonist of the androgen receptor, which modulates related gene expression to increase protein synthesis, further boosting muscle growth and increasing body mass as well as bone mineral density. However, it should be noted that its androgenic effect is less than its anabolic effect.

Uses

androgenic anabolic steroid;reverses catabolic tissue processes; promotes buildup of protein; increases erythropoietin production

Brand name

Oxandrin (Savient).

Uses

A synthetic, anabolic steroid. Used to promote muscle growth and combat involuntary weight loss. It has also been used to treat cases of osteoporosis.

Chemical Properties

White Solid

References

Li, H., et al. "The efficacy and safety of oxandrolone treatment for patients with severe burns: A systematic review and meta-analysis. " Burns Journal of the International Society for Burn Injuries 42.4(2016): 717.
Hart, D. W., et al. "Anabolic effects of oxandrolone after severe burn." Annals of Surgery 233.4(2001): 556-564.
Sheffieldmoore, M, et al. "Short-term oxandrolone administration stimulates net muscle protein synthesis in young men. " Journal of Clinical Endocrinology & Metabolism 84.8(1999): 2705-11.
https://en.wikipedia.org/wiki/Oxandrolone
InChI:InChI=1/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

53-39-4 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Sigma (SML0437)  Oxandrolone  ≥98% (HPLC) 53-39-4 SML0437-25MG 4,351.23CNY Detail
Sigma (SML0437)  Oxandrolone  ≥98% (HPLC) 53-39-4 SML0437-5MG 1,077.57CNY Detail

53-39-4Synthetic route

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

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

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

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

oxandrolone
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

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

oxandrolone
53-39-4

oxandrolone

Conditions
ConditionsYield
With potassium hydroxide In methanol; water at 50℃; for 3h;0.06 g
17α-methyl-1,3-seco-2-nor-5α-androstane-1,3,17α-triol
7745-45-1

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

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

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

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

oxandrolone
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
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
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

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

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

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

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

oxandrolone
53-39-4

oxandrolone

Conditions
ConditionsYield
With sodium borohydrid; sulfuric acid In water; N,N-dimethyl-formamide6.1 g (75.2%)
mestanolone
521-11-9

mestanolone

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

2α-bromo-17β-hydroxy-17α-methyl-5α-androstan-3-one

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

5α-17β-hydroxy-17α-methyl-Δ1-androsten-3-one

oxandrolone
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
oxandrolone
53-39-4

oxandrolone

17,17-dimethyl-18-nor-2-oxa-5α-androst-13(14)-en-3-one
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%
oxandrolone
53-39-4

oxandrolone

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

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%
oxandrolone
53-39-4

oxandrolone

A

6α-hydroxyoxandrolone
1207298-36-9

6α-hydroxyoxandrolone

B

11α-hydroxyoxandrolone
1207298-35-8

11α-hydroxyoxandrolone

C

9α-hydroxyoxandrolone
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%
pyridine
110-86-1

pyridine

oxandrolone
53-39-4

oxandrolone

oxandrolone 17β-sulfate pyridinium salt
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;
oxandrolone
53-39-4

oxandrolone

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
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;
oxandrolone
53-39-4

oxandrolone

17α-hydroxy-17β-methyl-2-oxa-5α-androstan-3-one
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
oxandrolone
53-39-4

oxandrolone

(5S,8R,9S,10S,13S,14S,17R)-10,13,17-Trimethyl-17-trimethylsilanyloxy-tetradecahydro-2-oxa-cyclopenta[a]phenanthren-3-one
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
oxandrolone
53-39-4

oxandrolone

17-epioxandrolone,TMS

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
chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

oxandrolone
53-39-4

oxandrolone

(4aS,4bS,6aS,7S,9aS,9bR,11aS)-7-(methoxymethoxy)-4a,6a,7-trimethyltetradeca-hydroindeno[4,5-h]isochromen-2(1H)-one
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;
N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide
24589-78-4

N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide

oxandrolone
53-39-4

oxandrolone

C22H38O3Si
136693-20-4

C22H38O3Si

Conditions
ConditionsYield
With ammonium iodide; 2-hydroxyethanethiol at 60℃; for 0.333333h;
oxandrolone
53-39-4

oxandrolone

A

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

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

B

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

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

C

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

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

D

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

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
oxandrolone
53-39-4

oxandrolone

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

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
oxandrolone
53-39-4

oxandrolone

A

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

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

B

C19H28O2

C19H28O2

Conditions
ConditionsYield
With pyridine; trichlorophosphate at 50℃; for 1.5h;
oxandrolone
53-39-4

oxandrolone

A

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

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

B

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

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

C

C19H28O3

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
oxandrolone
53-39-4

oxandrolone

A

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

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

B

C19H28O3

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

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