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Oxandrolone

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Name

Oxandrolone

EINECS 200-172-9
CAS No. 53-39-4 Density 1.105 g/cm3
PSA 46.53000 LogP 3.54310
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 N/A Appearance White crystalline powder
Safety 22-36/37/39-45 Risk Codes 60-63-20/21/22
Molecular Structure Molecular Structure of 53-39-4 (Oxandrolone) 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)-;

Article Data 9

Oxandrolone 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

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.

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