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57-85-2

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Basic Information
CAS No.: 57-85-2
Name: Androst-4-en-3-one,17-(1-oxopropoxy)-, (17b)-
Molecular Structure:
Molecular Structure of 57-85-2 (Androst-4-en-3-one,17-(1-oxopropoxy)-, (17b)-)
Formula: C22H32O3
Molecular Weight: 344.49
Synonyms: Testosterone,propionate (8CI);17b-(Propionyloxy)androst-4-en-3-one;Agovirin;Androlon;Bio-testiculina;Enarmon;Enarmon-oil;Homandren;Hormoteston;Masenate;Nasdol;Orchisterone;Orchistin;Oreton;Pantestin;Primotestone;Propiokan;Sterandryl;Synerone;TP;Telipex;Testaform;Testex;Testonique;Testosid;Testosterone-17-propionate;Testrex;Testosterone Propionate;17-(1-oxopropoxy)-(17b)-androst-4-en-3-one;
EINECS: 200-351-1
Density: 1.1 g/cm3
Melting Point: 118-123 °C
Boiling Point: 454.6 °C at 760 mmHg
Flash Point: 196.3 °C
Solubility: <0.1 g/100 mL at 24.5 °C in water
Appearance: white or yellowish-white crystals or a white or creamy-white crystalline powder
Hazard Symbols: ToxicT
Risk Codes: 45-22-63
Safety: 53-36/37-45
Transport Information: UN 2811
PSA: 43.37000
LogP: 4.84010
Synthetic route
79-03-8

propionyl chloride

975-57-5

3,3-(ethylenedioxy)-5-androsten-17β-ol

57-85-2

testosterone propionate

Conditions
ConditionsYield
Stage #1: propionyl chloride; 3,3-(ethylenedioxy)-5-androsten-17β-ol With pyridine; dmap In 1,2-dichloro-ethane at 30℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water
97.4%
802294-64-0

propionic acid

17β-hydroxy-3-methoxyandrosta-3,5-diene

57-85-2

testosterone propionate

Conditions
ConditionsYield
Stage #1: propionic acid; 17β-hydroxy-3-methoxyandrosta-3,5-diene With diisopropyl-carbodiimide In dichloromethane at 5℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water
97.36%

(8S,9S,10R,13S,14S,17S)-4,5-dibromo-10,13-dimethyl-3-oxohexadecahydro-1Hcyclopenta[a]phenanthren-17-yl propionate

57-85-2

testosterone propionate

Conditions
ConditionsYield
With 1,1'-bis(trimethylsilyl)-1,1',4,4'-tetrahydro-4,4'-bipyridylidene In acetonitrile at 20℃; for 2h; Inert atmosphere;89%
58-22-0

testosterone

79-03-8

propionyl chloride

57-85-2

testosterone propionate

Conditions
ConditionsYield
With pyridine In N,N-dimethyl acetamide at 0 - 20℃; for 5h; Inert atmosphere;73%
With immobilized p-toluenesulfonic acid polymer bound macroporous In neat (no solvent) at 100℃; for 0.0416667h; Microwave irradiation; Sealed tube; Green chemistry;65%
With pyridine; diethyl ether
With pyridine; dmap In dichloromethane at 5℃; Inert atmosphere;10.2 g
4076-66-8

androsten-(4)-yl-(17β)-propionate

57-85-2

testosterone propionate

Conditions
ConditionsYield
With chromium(VI) oxide; acetic acid
With chromium(VI) oxide; acetic acid
63088-08-4

3-acetoxy-17β-(1-oxopropoxy)-androsta-3,5-diene

57-85-2

testosterone propionate

Conditions
ConditionsYield
With ethanol; potassium carbonate
38859-47-1

17β-propionyloxy-androst-5-en-3β-ol

57-85-2

testosterone propionate

Conditions
ConditionsYield
With bromine; acetic acid nachfolgendes Behandeln mit CrO3 in wss.Essigsaeure und Erwaermen der Reaktionsloesung mit Zink-Pulver und Essigsaeure;
With copper at 225℃; unter vermindertem Druck;
58-22-0

testosterone

123-62-6

propionic acid anhydride

57-85-2

testosterone propionate

Conditions
ConditionsYield
With pyridine at 125℃;
With pyridine at 25℃;
Stage #1: testosterone With pyridine at 80℃; for 0.5h;
Stage #2: propionic acid anhydride With dmap at 25℃; for 3.75h;
166.5 g
17β-propionyloxy-5α-androstanone-(3)

17β-propionyloxy-5α-androstanone-(3)

57-85-2

testosterone propionate

Conditions
ConditionsYield
With bromine kurzes Erhitzen des erhaltenen 2α-Brom-17β-propionyloxy-5α-androstanons-(3) mit Pyridin auf Siedetemperatur und Erhitzen des Reaktionsprodukts unter 12 Torr bis auf 400grad;
Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetone; aluminium isobutylate; benzene
2: pyridine / 25 °C
View Scheme
58-22-0

testosterone

57-85-2

testosterone propionate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / 40 °C / Inert atmosphere
2: dmap; pyridine / 1,2-dichloro-ethane / 30 °C / Inert atmosphere
View Scheme
972-46-3

3-ethoxyandrosta-3,5-dien-17-one

57-85-2

testosterone propionate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium borohydride; pyridine / ethanol / 60 °C
2: hydrogenchloride / water; tetrahydrofuran / 20 - 30 °C
3: orthoformic acid triethyl ester; toluene-4-sulfonic acid / 40 °C / Inert atmosphere
4: dmap; pyridine / 1,2-dichloro-ethane / 30 °C / Inert atmosphere
View Scheme
26614-48-2

17β-hydroxy-3-ethoxyandrosta-3,5-diene

57-85-2

testosterone propionate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / water; tetrahydrofuran / 20 - 30 °C
2: orthoformic acid triethyl ester; toluene-4-sulfonic acid / 40 °C / Inert atmosphere
3: dmap; pyridine / 1,2-dichloro-ethane / 30 °C / Inert atmosphere
View Scheme
63-05-8

Androstenedione

57-85-2

testosterone propionate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridinium p-toluenesulfonate / methanol / 20 °C / Inert atmosphere
2: pyridine; sodium tetrahydroborate / methanol / 40 °C
3: diisopropyl-carbodiimide / dichloromethane / 5 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1: pyridinium p-toluenesulfonate / ethanol / 40 °C / Inert atmosphere
2: potassium borohydride; pyridine / ethanol / 60 °C
3: hydrogenchloride / water; tetrahydrofuran / 20 - 30 °C
4: orthoformic acid triethyl ester; toluene-4-sulfonic acid / 40 °C / Inert atmosphere
5: dmap; pyridine / 1,2-dichloro-ethane / 30 °C / Inert atmosphere
View Scheme
57144-06-6

3-methoxyandrosta-3,5-dien-17-one

57-85-2

testosterone propionate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine; sodium tetrahydroborate / methanol / 40 °C
2: diisopropyl-carbodiimide / dichloromethane / 5 °C / Inert atmosphere
View Scheme
57-85-2

testosterone propionate

107-21-1

ethylene glycol

81275-73-2

5-androstene-17β-propionyloxy-3-spiro-2'-(1',3'-dioxolane)

Conditions
ConditionsYield
With montmorillonite K-10 In benzene for 2h; Heating;99%
With toluene-4-sulfonic acid; benzene
57-85-2

testosterone propionate

3510-18-7

5-oxo-17β-propionyloxy-4-nor-3,5-secoandrostan-3-oic acid

Conditions
ConditionsYield
With potassium permanganate; sodium periodate; potassium carbonate In water; tert-butyl alcohol for 4.5h; Ambient temperature;94%
Stage #1: testosterone propionate With ozone In ethyl acetate at -78℃; ozonolysis;
Stage #2: With dihydrogen peroxide In water at 20℃; Reduction;
87%
57-85-2

testosterone propionate

78948-09-1

acetyl hypofluorite

androstane-5α-acetoxy-4α-fluoro-17β-ol-3-one propionate

Conditions
ConditionsYield
In chloroform for 0.0833333h;89%
57-85-2

testosterone propionate

75-36-5

acetyl chloride

63088-08-4

3-acetoxy-17β-(1-oxopropoxy)-androsta-3,5-diene

Conditions
ConditionsYield
With pyridine; acetic anhydride for 3h; Heating;88.5%
57-85-2

testosterone propionate

A

35471-70-6, 71788-18-6

Propionic acid (5R,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl ester

B

35471-70-6, 71788-18-6

Propionic acid (5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl ester

Conditions
ConditionsYield
With hydrogen; Cu/Al2O3 In toluene at 60℃; under 760 Torr;A 85%
B 15%
57-85-2

testosterone propionate

156-57-0

2-mercaptoethylamine hydrochloride

81275-72-1

5-androstene-17β-propionyloxy-3-spiro-2'-(1',3'-thiazolidine)

Conditions
ConditionsYield
In pyridine Ambient temperature;71%
57-85-2

testosterone propionate

A

855-22-1

3-oxo-5α-androstan-17β-ol propionate

B

35471-70-6, 71788-18-6

Propionic acid (5R,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl ester

C

18179-14-1

3-oxo-5β-androstan-17β-ol propionate

Conditions
ConditionsYield
With hydrogen; Cu/Al2O3 In toluene at 60℃; under 760 Torr;A 11%
B 12%
C 65%
57-85-2

testosterone propionate

androstan-3-one-4,5-difluoro-17β-hydroxy propionate

Conditions
ConditionsYield
With fluorine In ethanol; chloroform; trichlorofluoromethane at -78℃; Inert atmosphere;65%
57-85-2

testosterone propionate

A

566-08-5

15α-hydroxyandrost-4-ene-3,17-dione

B

4416-57-3

testololactone

C

7801-32-3

17a-oxa-D-homo-5α-androstane-3,17-dione

Conditions
ConditionsYield
With Penicillium notatum KCH 904 In water; acetone at 27℃; for 96h; Enzymatic reaction;A 29%
B 61%
C 9%
57-85-2

testosterone propionate

107-21-1

ethylene glycol

A

81275-73-2

5-androstene-17β-propionyloxy-3-spiro-2'-(1',3'-dioxolane)

B

81240-03-1

4-androstene-17β-propionyloxy-3-spiro-2'-(1',3'-dioxolane)

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 5h; Heating;A 28%
B 15%
57-85-2

testosterone propionate

868-59-7

L-cysteine ethyl ester hydrochloride

A

82890-36-6

5-androstene-17β-propionyloxy-3-spiro-2'-(4'-ethoxycarbonyl-1',3'-thiazolidine)

B

82890-37-7

4-androstene-17β-propionyloxy-3-spiro-2'-(4'-ethoxycarbonyl-1',3'-thiazolidine)

Conditions
ConditionsYield
In pyridine Ambient temperature; Yields of byproduct given;A 26%
B n/a
In pyridine Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
57-85-2

testosterone propionate

60-24-2

2-hydroxyethanethiol

A

81240-02-0

4-androstene-17β-propionyloxy-3-spiro-2'-(1',3'-oxathiolane)

B

81240-01-9

5-androstene-17β-propionyloxy-3-spiro-2'-(1',3'-oxathiolane)

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 7h; Heating;A 12%
B 16%
57-85-2

testosterone propionate

58-22-0

testosterone

Conditions
ConditionsYield
With lipase from Candida cylindracea; octanol In various solvent(s) at 37℃; for 144h;12%
With water In methanol at 40℃; Rate constant; pH 9, also reaction in the presence of 2-hydroxypropyl-β-cyclodextrin;
With Novozyme 51032 In aq. phosphate buffer at 52.5℃; for 24h; pH=8.5; Reagent/catalyst; Temperature; pH-value; Enzymatic reaction;
57-85-2

testosterone propionate

120022-91-5

6ζ-(3-Oxo-17β-propionyloxy-5ζ-androstan-4-ζ-yl)-17β-propionyloxyandrost-4-en-3-on

Conditions
ConditionsYield
With aerosile for 48h; Irradiation;10.4%
126-39-6

2-ethyl-2-methyl-1,3-dioxolane

57-85-2

testosterone propionate

81275-73-2

5-androstene-17β-propionyloxy-3-spiro-2'-(1',3'-dioxolane)

Conditions
ConditionsYield
With toluene-4-sulfonic acid
110-86-1

pyridine

57-85-2

testosterone propionate

1-(17β-propionyloxy-androsta-3,5-dien-3-yl)-pyridinium; chloride

Conditions
ConditionsYield
With trichlorophosphate
74-96-4

ethyl bromide

57-85-2

testosterone propionate

4,4-diethyl-17β-hydroxy-androst-5-en-3-one

Conditions
ConditionsYield
With isopropyl alcohol; sodium t-butanolate; tert-butyl alcohol
917-64-6

methyl magnesium iodide

57-85-2

testosterone propionate

3-methyl-androst-4-ene-3ξ,17β-diol

Conditions
ConditionsYield
With diethyl ether
57-85-2

testosterone propionate

75-16-1

methylmagnesium bromide

3-methyl-androst-4-ene-3ξ,17β-diol

Conditions
ConditionsYield
With diethyl ether
In diethyl ether Heating;
57-85-2

testosterone propionate

2162-45-0

4-bromo-17β-propionyloxy-androst-4-en-3-one

Conditions
ConditionsYield
With oxirane; bromine
With 2,4,6-trimethyl-pyridine; bromine
With bromine azide
Multi-step reaction with 2 steps
1: NBS, HN3 / CHCl3; 2-methyl-propan-2-ol
2: SiO2 / benzene
View Scheme
Multi-step reaction with 2 steps
1: NBS, HN3 / CHCl3; 2-methyl-propan-2-ol
2: SiO2 / benzene
View Scheme
57-85-2

testosterone propionate

114794-73-9

4β,5-dichloro-17β-propionyloxy-5α-androstan-3-one

Conditions
ConditionsYield
With 1,4-dioxane; diethyl ether; chlorine; propionic acid
57-85-2

testosterone propionate

5996-42-9

17β-propionyloxy-androst-4-en-3-one oxime

Conditions
ConditionsYield
With hydroxylamine
57-85-2

testosterone propionate

117272-05-6

17β,17'β-bis-propionyloxy-3βH,3'βH-[3,3']biandrost-4-enyl-3,3'-diol

Conditions
ConditionsYield
With lithium chloride Reduktion an Quecksilber-Kathoden;
Downstream Products
58-22-0
1156-92-9
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Specification

The Testosterone Propionate, with the cas registry number 57-85-2, has its systematic name of (17beta)-3-oxoandrost-4-en-17-yl propanoate. This is a kind of white solid and is insoluble in water, and it belongs to the product categories of steroids. As to its usage, it is usually applied for curing breast cancer, oophoroma, myoma of uterus, Huppert's [Kahler's] disease, kidney cancer and so on.

The characteristics of this chemical are as following: (1)ACD/LogP: 4.90 ; (2)ACD/LogD (pH 5.5): 4.9; (3)ACD/LogD (pH 7.4): 4.9; (4)ACD/BCF (pH 5.5): 3132.11; (5)ACD/BCF (pH 7.4): 3132.11; (6)ACD/KOC (pH 5.5): 11064.07; (7)ACD/KOC (pH 7.4): 11064.07; (8)#H bond acceptors: 3  ; (9)#Freely Rotating Bonds: 3; (10)Polar Surface Area: 43.37; (11)Index of Refraction: 1.537; (12)Molar Refractivity: 97.32 cm3; (13)Molar Volume: 311.2 cm3; (14)Polarizability: 38.58 ×10-24 cm3; (15)Surface Tension: 42 dyne/cm; (16)Density: 1.1 g/cm3; (17)Flash Point: 196.3 °C; (18)Enthalpy of Vaporization: 71.42 kJ/mol; (19)Boiling Point: 454.6 °C at 760 mmHg; (20)Vapour Pressure: 1.89E-08 mmHg at 25°C; (21)Tautomer Count: 5 ; (22)Exact Mass: 344.235145 ; (23)MonoIsotopic Mass: 344.235145 ; (24)Topological Polar Surface Area: 43.4 ; (25)Heavy Atom Count: 25.

When you deal with this chemical, you should be very cautious. For as a kind of toxic chemical, it may at low levels cause damage to health, and even could cause cancer. If swallowed, it is very harmful; Besides, it has possible risk of harm to the unborn child. Therefore, you should take the following instructions. Wear suitable protective clothing and gloves, and avoid exposure - obtain special instructions before use. If in case of accident or if you feel unwell seek medical advice immediately (show the label where possible). 

In addition, you could convert the following datas into the molecular structure:
(1)SMILES:O=C4\C=C2/[C@]([C@H]1CC[C@@]3([C@@H](OC(=O)CC)CC[C@H]3[C@@H]1CC2)C)(C)CC4
(2)InChI:InChI=1/C22H32O3/c1-4-20(24)25-19-8-7-17-16-6-5-14-13-15(23)9-11-21(14,2)18(16)10-12-22(17,19)3/h13,16-19H,4-12H2,1-3H3/t16-,17-,18-,19-,21-,22-/m0/s1

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 970mg/kg (970mg/kg)   Drugs in Japan Vol. 6, Pg. 487, 1982.
mouse LD50 oral 1350mg/kg (1350mg/kg)   Drugs in Japan Vol. 6, Pg. 487, 1982.
mouse LD50 subcutaneous > 5gm/kg (5000mg/kg)   Drugs in Japan Vol. 6, Pg. 487, 1982.
rat LD50 intraperitoneal 585mg/kg (585mg/kg)   Drugs in Japan Vol. 6, Pg. 487, 1982.
rat LD50 oral 1gm/kg (1000mg/kg)   Drugs in Japan Vol. 6, Pg. 487, 1982.
rat LD50 subcutaneous > 5gm/kg (5000mg/kg)   Drugs in Japan Vol. 6, Pg. 487, 1982.