Name: Androstenedione
SKU: 63-05-8

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Basic Information

Molecular Structure:
CAS No.:	63-05-8
Name:	Androstenedione

Formula:	C₁₉H₂₆O₂
Molecular Weight:	286.414
Synonyms:	17-Ketotestosterone;3,17-Dioxoandrost-4-ene;4-Androstene-3,17-dione;Androstenedione;Fecundin;NSC 9563;SKF 2170;D4-Androstene-3,17-dione;Androstenedione;4-Androstenedione;
EINECS:	200-554-5
Density:	1.11 g/cm³
Melting Point:	170-171 °C(lit.)
Boiling Point:	431.4 °C at 760 mmHg
Flash Point:	161.1 °C
Solubility:	57.28mg/L(25 oC)
Appearance:	white to off-white solid
Hazard Symbols:	Xn
Risk Codes:	40
Safety:	22-24/25-36
PSA:	34.14000
LogP:	4.08740

Synthetic route

: 58-22-0
testosterone

: 63-05-8
Androstenedione

Conditions

Conditions	Yield
With Jones reagent In acetone at 0℃; Jones Oxidation;	100%
With oxygen; nitrosonium tetrafluoroborate In dichloromethane at 20℃; for 4h;	99%
With N-chloro-succinimide; dodecyl methyl sulfide; triethylamine In toluene at -40℃; for 16h; Corey-Kim oxidation;	97%

: 25375-38-6
3-hydroxy-5-androsten-17-one

: 63-05-8
Androstenedione

Conditions

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ferric nitrate In ethyl acetate at 0℃; for 65h; Reagent/catalyst;	100%

: 68-96-2
17-hydroxyprogesterone

: 63-05-8
Androstenedione

Conditions

Conditions	Yield
In water; acetonitrile at 20℃; Electrochemical reaction;	99%
With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide In dichloromethane; acetonitrile for 0.75h;	95%
With chromium(VI) oxide; acetic acid

: 4966-70-5
3,3,17,17-diethylenedioxyandrost-5-ene

: 63-05-8
Androstenedione

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water at 40℃; for 2h; pH=3; Temperature; Green chemistry;	98.6%
With sulfuric acid; water; silica gel In toluene for 2h;	92%
Multi-step reaction with 4 steps 1: hydrogenchloride / water; acetone / pH 1-6 2: potassium tert-butylate / tetrahydrofuran / Inert atmosphere; Reflux 3: tetrahydrofuran / Acidic conditions 4: sodium hydrogencarbonate; ruthenium trichloride; Oxone / ethyl acetate; acetonitrile; water / -20 - 30 °C View Scheme

: 2283-82-1
3α-hydroxy-androst-5-en-17-one

: 63-05-8
Androstenedione

Conditions

Conditions	Yield
With calcium hypochlorite; acetic acid In ethyl acetate at 30℃; for 1h; Temperature; Green chemistry;	98.5%

: 81176-75-2
(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[α]phenanthrene-3,17-diol

: 63-05-8
Androstenedione

Conditions

Conditions	Yield
With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide In dichloromethane for 0.5h;	98%
With 9-fluorenone; oxygen In dimethyl sulfoxide at 20℃; Irradiation;	72%

: 571-36-8
5-androstenedione

: 63-05-8
Androstenedione

Conditions

Conditions	Yield
With potassium hydroxide In methanol; water Ambient temperature;	97%
With sodium hydroxide In methanol; water at 25℃;
With sodium hydroxide; 3-oxo-Δ5-steroid isomerase In methanol; water Rate constant; pH 5.0 to 5.1;

: 162657-73-0
3-cycloethylenedithio-17-cycloethylenedioxy-androst-4-ene

: 63-05-8
Androstenedione

Conditions

Conditions	Yield
With silica gel; copper(II) sulfate In benzene at 80℃; for 5h;	90%

: 53-43-0
dehydroepiandrosterone

A: 63-05-8
Androstenedione

B: 5982-99-0
androstane-3,17-dione

Conditions

Conditions	Yield
aluminum oxide; copper In toluene at 60℃;	A 12% B 88%

: 152-58-9
Cortexolone

: 63-05-8
Androstenedione

Conditions

Conditions	Yield
In water; acetonitrile at 20℃; Electrochemical reaction;	86%
With ammonium hydroxide; iodine In water; acetonitrile at 50℃; for 24h;	78%
With manganese(IV) oxide In chloroform for 4h; Heating;	67.6%

Raw Materials

108-24-7

10035-10-6

67-64-1

71-43-2

67-66-3

145-13-1

152-58-9

108-75-8

Downstream Products

63-00-3

968-49-0

62-83-9

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History

Androstenedione was manufactured as a dietary supplement, often called andro for short.
Andro was legal and able to be purchased over the counter and consequently it was common use in Major League Baseball throughout the 1990s by record-breaking sluggers like Mark McGwire. The supplement is banned by the World Anti-Doping Agency, and hence from the Olympic Games.
On March 12, 2004, the Anabolic Steroid Control Act of 2004 was introduced into the United States Senate. The law took effect on January 20, 2005. Surprisingly, andro was legally defined as an anabolic steroid, even though there is scant evidence that androstenedione itself is anabolic in nature.
On April 11, 2004, the United States Food and Drug Administration banned the sale of Andro.
Androstenedione is currently banned by the US military.

Specification

The Androstenedione is an organic compound with the formula C₁₉H₂₆O₂. The IUPAC name of this chemical is (8R,9S,10R,13S,14S)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione. With the CAS registry number 63-05-8, it is also named as 4-Androsten-3,17-dione. The product's categories are Pharmaceutical Intermediates; Steroids; Metabolites & Impurities. Besides, it is a white to off-white solid, which should be stored in a closed place. It is used for biochemical studies.

Physical properties about Androstenedione are: (1)ACD/LogP: 2.90; (2)ACD/LogD (pH 5.5): 2.9; (3)ACD/LogD (pH 7.4): 2.9; (4)ACD/BCF (pH 5.5): 93.64; (5)ACD/BCF (pH 7.4): 93.64; (6)ACD/KOC (pH 5.5): 896.96; (7)ACD/KOC (pH 7.4): 896.96; (8)#H bond acceptors: 2; (9)Polar Surface Area: 34.14 Å²; (10)Index of Refraction: 1.551; (11)Molar Refractivity: 81.71 cm³; (12)Molar Volume: 255.8 cm³; (13)Polarizability: 32.39×10^-24cm³; (14)Surface Tension: 42.6 dyne/cm; (15)Density: 1.11 g/cm³; (16)Flash Point: 161.1 °C; (17)Enthalpy of Vaporization: 68.71 kJ/mol; (18)Boiling Point: 431.4 °C at 760 mmHg; (19)Vapour Pressure: 1.2E-07 mmHg at 25°C.

Preparation: this chemical can be prepared by 17-hydroxy-androst-4-en-3-one. This reaction will need reagent CrO₃ and acetic acid.

Uses of Androstenedione: it can be used to produce 5,17-dioxo-3,5-seco-A-nor-androstan-3-oic acid. It will need reagent KMnO₄ and acetone.

When you are using this chemical, please be cautious about it as the following:
It has limited evidence of a carcinogenic effect. When you are using it, wear suitable protective clothing, do not breathe dust and avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C4/C=C3/CC[C@@H]2[C@H](CC[C@@]1(C(=O)CC[C@H]12)C)[C@@]3(C)CC4
(2)InChI: InChI=1/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
(3)InChIKey: AEMFNILZOJDQLW-QAGGRKNEBJ
(4)Std. InChI: InChI=1S/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
(5)Std. InChIKey: AEMFNILZOJDQLW-QAGGRKNESA-N

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Specification