Androst-5-en-3-ol-7,17-dione acetate supplier

Name
Androst-5-en-3-ol-7,17-dione acetate
EINECS 683-490-4
CAS No. 1449-61-2
Article Data50
CAS DataBase
Density 1.18 g/cm³
Solubility
Melting Point 184.5-187.5 °C
Formula C₂₁H₂₈O₄
Boiling Point 479.638 °C at 760 mmHg
Molecular Weight 344.451
Flash Point 209.21 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Androst-5-ene-7,17-dione,3b-hydroxy-, acetate (6CI,7CI,8CI);3b-Acetoxy-5-androsten-7,17-dione;3b-Acetoxyandrost-5-ene-7,17-dione;3b-O-Acetyl-7-oxodehydroepiandrosterone;5-Androsten-3b-ol-7,17-dione acetate;7-Keto Naturalean;7-Oxodehydroepiandrosterone acetate;NSC 134911;
PSA 60.44000
LogP 3.62900

Synthetic route

: 566-19-8
5-androstene-3β-ol-7,17-dione

: 108-24-7
acetic anhydride

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

Conditions

Conditions	Yield
With toluene-4-sulfonic acid for 0.0333333h; microwave irradiation;	96%
for 3h; Reflux;	85%

: 853-23-6
prasterone acetate

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

Conditions

Conditions	Yield
With N-hydroxyphthalimide; sodium dichromate; chromium(III) perchlorate In water; acetonitrile at 20℃; for 48h; Product distribution / selectivity;	93%
With tert.-butylhydroperoxide; N-hydroxyphthalimide; cobalt(II) acetate In acetone at 20℃; for 5h; regioselective reaction;	93.7%
Stage #1: prasterone acetate With tert.-butylhydroperoxide; 3 A molecular sieve In decane; ethyl acetate at 20℃; for 0.5h; Stage #2: With manganese triacetate In decane; ethyl acetate at 20℃; for 30h;	91%

: 853-23-6
prasterone acetate

A: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

B: 39933-10-3
3β,5-dihydroxy-5α-androstane-6,17-dione 3-acetate

C: 6585-68-8
3β-acetoxy-5β,6β-epoxyandrostan-17-one

Conditions

Conditions	Yield
With chromyl acetate In dichloromethane at -78℃; for 0.25h;	A 30 mg B 60 mg C 77%

...Expand

: 853-23-6
prasterone acetate

A: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

B: 37976-94-6
7α-hydroxy-17-oxoandrost-5-ene-3β-yl acetate

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; manganese(IV) oxide In dichloromethane; water at -20℃; for 22h; Reflux; regioselective reaction;	A 75% B 13%

: 853-23-6
prasterone acetate

A: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

B: 929270-02-0
(3S,6aR,6bS,9aS,11aS,11bR)-9a,11b-dimethyl-9-oxohexadecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-3-yl acetate

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; chromium(VI) oxide In dichloromethane for 24h; Ambient temperature;	A 52% B 8%

: 853-23-6
prasterone acetate

A: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

B: 37976-94-6
7α-hydroxy-17-oxoandrost-5-ene-3β-yl acetate

C: 6585-68-8
3β-acetoxy-5β,6β-epoxyandrostan-17-one

D: 14545-93-8
5α,6α-epoxy-17-oxoandrostan-3β-yl acetate

Conditions

Conditions	Yield
With ferric picolinate complexes; dihydrogen peroxide In acetonitrile for 3h; Ambient temperature;	A 22% B 39.3% C 1.9% D 0.7%
With ferric picolinate complexes; dihydrogen peroxide In acetonitrile for 3h; Ambient temperature;	A 22% B 39.3% C 1.9% D 0.7%

...Expand

: 84412-82-8
3β-acetoxy-17-picolinylidene-androst-5-ene

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

Conditions

Conditions	Yield
With chromium(VI) oxide In acetic anhydride; acetic acid at 90 - 95℃; for 1h;	10.6%

: 84412-82-8
3β-acetoxy-17-picolinylidene-androst-5-ene

A: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

B: 83830-40-4
3β-acetoxy-17-picolinylidene-5-androstene-7-one

Conditions

Conditions	Yield
With chromium(VI) oxide In water; acetic acid at 90 - 95℃; for 1h;	A 9.8% B 8.9%

: 853-23-6
prasterone acetate

A: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

B: 6585-68-8
3β-acetoxy-5β,6β-epoxyandrostan-17-one

C: 14545-93-8
5α,6α-epoxy-17-oxoandrostan-3β-yl acetate

Conditions

Conditions	Yield
With Mn(OTf)2(dMMpdp); dihydrogen peroxide; trimethylpyruvic acid In water; ethyl acetate; acetonitrile at 20℃; for 1h; Reagent/catalyst; diastereoselective reaction;	A 8% B n/a C n/a
With Fe(OTf)2(dMMpdp); dihydrogen peroxide; trimethylpyruvic acid In water; ethyl acetate; acetonitrile at 20℃; for 1h; diastereoselective reaction;	A 2% B n/a C n/a

...Expand

: 853-23-6
prasterone acetate

A: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

B: 98128-97-3
3β-acetoxy-5,20-dioxo-5,6-secoandrostan-6-oic acid

Conditions

Conditions	Yield
With chromium(VI) oxide; acetic acid

: 27270-51-5
3β-acetoxy-7α-azidoandrost-5-en-17-one

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

Conditions

Conditions	Yield
With lead(IV) acetate; trimethylsilylazide

: 1639-43-6
androstenediol-3-acetate

A: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

B: 55935-02-9
3β-acetoxy-17β-hydroxy-5-androsten-7-one

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; copper(l) iodide In decane; acetonitrile at 50℃; for 24h; Title compound not separated from byproducts;	A n/a B 70 % Spectr.
With tert.-butylhydroperoxide; cobalt(II) acetate In decane; acetonitrile at 55℃; for 24h;	A n/a B 70 % Spectr.

: 853-23-6
prasterone acetate

A: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

B: 528870-28-2
3β,6α-diacetoxy-5-hydroxy-5α-androstan-17-one

C: 6585-68-8
3β-acetoxy-5β,6β-epoxyandrostan-17-one

D: 14545-93-8
5α,6α-epoxy-17-oxoandrostan-3β-yl acetate

Conditions

Conditions	Yield
With potassium permanganate; sodium perborate; acetic acid Ambient temperature;	A 30 mg B 73 mg C 292 mg D 67 mg

...Expand

: 853-23-6
prasterone acetate

: 64-19-7
acetic acid

A: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

B: 528870-28-2
3β,6α-diacetoxy-5-hydroxy-5α-androstan-17-one

C: 6585-68-8
3β-acetoxy-5β,6β-epoxyandrostan-17-one

D: 14545-93-8
5α,6α-epoxy-17-oxoandrostan-3β-yl acetate

Conditions

Conditions	Yield
With potassium permanganate; sodium perborate Ambient temperature;	A 30 mg B 73 mg C 292 mg D 67 mg

...Expand

: 108-24-7
acetic anhydride

3β-hydroxy-androstene-(5)-dione-(7.17): 3β-hydroxy-androstene-(5)-dione-(7.17)

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

Conditions

Conditions	Yield
With pyridine

: 53-43-0
dehydroepiandrosterone

: 108-24-7
acetic anhydride

A: 2863-23-2
3β,7α-diacetoxyandrost-5-en-17-one

B: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

C: 3β,7α,17β-triacetoxyandrost-5-ene

Conditions

Conditions	Yield
Stage #1: dehydroepiandrosterone With fungus Fusarium oxysporum var. cubense In ethanol at 27℃; for 180h; biotransformation; Acetylation; Microbiological reaction; fungus from rhizome of banana plant showing symptoms of Panama disease; Stage #2: acetic anhydride With pyridine at 60℃;

...Expand

: 53-43-0
dehydroepiandrosterone

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: acetic acid; sodium acetate / 18 h / 65 °C 1.2: 94 percent / H2O / 4 h / 20 °C View Scheme

aqueous sodium hypochlorite: aqueous sodium hypochlorite

: 53-43-0
dehydroepiandrosterone

: 853-23-6
prasterone acetate

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; sodium hydroxide; sodium acetate; sodium sulfite In water; acetic anhydride; ethyl acetate

...Expand

: 53-43-0
dehydroepiandrosterone

A: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

B: 37976-94-6
7α-hydroxy-17-oxoandrost-5-ene-3β-yl acetate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine 2: tert.-butylhydroperoxide; manganese(IV) oxide / water; dichloromethane / 22 h / -20 °C / Reflux View Scheme

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

: 13258-27-0
3β-Acetoxy-7,17-dioxo-5α-androstan

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 25℃; under 775.743 Torr; for 48h;	97%
With hydrogen; Lindlar's catalyst In 1,4-dioxane
With hydrogen; palladium on activated charcoal In isopropyl alcohol
With hydrogen; palladium on activated charcoal In ethanol

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

: Acetic acid (3S,5R,6R,8R,9S,10R,13S,14S)-5,6-dihydroxy-10,13-dimethyl-7,17-dioxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester

Conditions

Conditions	Yield
With osmium(VIII) oxide In pyridine for 2.5h; Ambient temperature;	88%

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

: 55935-02-9
3β-acetoxy-17β-hydroxy-5-androsten-7-one

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol; ethyl acetate at 0℃; for 0.333333h;	82%
With lithium tri(t-butoxy)aluminum hydride In tetrahydrofuran for 0.116667h; Ambient temperature;

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

: 3β-acetoxy-17a-oxo-androst-5-ene-7,17-dione

Conditions

Conditions	Yield
With peracetic acid; toluene-4-sulfonic acid; acetic acid at 20℃; for 18h; Baeyer-Villiger reaction;	67%

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

: 3β-acetoxyandrostane-7,17-dione

Conditions

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In ethanol under 760.051 Torr; for 2h;	60%
With hydrogen; palladium 10% on activated carbon In ethanol under 760.051 Torr; for 2h;	60%
With hydrogen; palladium 10% on activated carbon In ethanol under 760.051 Torr; for 2h;	60%

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

: 13209-60-4
3β, 17β-diacetoxyandrost-5-ene-7-one

Conditions

Conditions	Yield
With lithium tri-t-butoxyaluminum hydride und anschliessend mit Acetanhydrid;

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

: 3β-Acetoxy-5-androsten-7α,17β-diol

Conditions

Conditions	Yield
With sodium tetrahydroborate In 1,4-dioxane; ethanol Ambient temperature;

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

: 3β-acetoxyandrost-5-ene-7β,17β-diol

Conditions

Conditions	Yield
With sodium tetrahydroborate In 1,4-dioxane; ethanol Ambient temperature;

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

: 98-88-4
benzoyl chloride

: 123131-09-9
5,7-bisdehydro-3β-acetoxy-17β-benzoyloxy-androstane

Conditions

Conditions	Yield
(i) NaBH4 (ii) /BRN= 471389/, Py, (iii) N,N-dimethylaniline; Multistep reaction;

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

: 87126-22-5
3β-Acetoxy-5,17-dioxo-5,7-seco-B-nor-androstan-7-oic acid

Conditions

Conditions	Yield
(i) O3, O2, AcOH, AcOEt, (ii) aq. H2SO4; Multistep reaction;

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

: 98-88-4
benzoyl chloride

: 71583-35-2
3β-acetoxy-17β-benzoyloxyandrost-5-en-7-one

Conditions

Conditions	Yield
(i) Li, THF, (ii) /BRN= 471389/, Py; Multistep reaction;

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

: 4147-15-3
5α-androstane-3,7,17-trione

Conditions

Conditions	Yield
(i) H2, Pd-C, EtOH, (ii) aq. K2CO3, MeOH, (iii) aq. CrO3, H2SO4, acetone; Multistep reaction;
Multi-step reaction with 3 steps 1: H2 / Pd-C / ethanol 2: NaOH / methanol / Heating 3: CrO3, Py View Scheme

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

: 566-19-8
5-androstene-3β-ol-7,17-dione

Conditions

Conditions	Yield
With sodium carbonate In methanol
With sodium hydrogencarbonate In methanol	307 mg

: 75-77-4
chloro-trimethyl-silane

: 5707-04-0
Phenylselenyl chloride

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

A: 216484-82-1
Acetic acid (3S,8R,9S,10R,13S,14S,16R)-10,13-dimethyl-7,17-dioxo-16-phenylselanyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

B: Trimethylsilanyl-acetic acid (3S,8R,9S,10R,13S,14S,16R)-10,13-dimethyl-7,17-dioxo-16-phenylselanyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Conditions

Conditions	Yield
With pyridine; water; lithium diisopropyl amide Multistep reaction. Title compound not separated from byproducts;

...Expand

: 75-77-4
chloro-trimethyl-silane

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

A: Acetic acid (3S,8R,9S,10R,13S,14S)-10,13-dimethyl-7-oxo-17-trimethylsilanyloxy-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

B: Trimethylsilanyl-acetic acid (3S,8R,9S,10R,13S,14S)-10,13-dimethyl-7-oxo-17-trimethylsilanyloxy-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Conditions

Conditions	Yield
With water; lithium diisopropyl amide 1.) THF, hexane, from -78 deg C to RT, 2.) Et2O, 15 min; Multistep reaction. Title compound not separated from byproducts;

...Expand

: 5707-04-0
Phenylselenyl chloride

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

: 216484-82-1
Acetic acid (3S,8R,9S,10R,13S,14S,16R)-10,13-dimethyl-7,17-dioxo-16-phenylselanyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Conditions

Conditions	Yield
With pyridine; chloro-trimethyl-silane; tetrabutyl ammonium fluoride; water; lithium diisopropyl amide Yield given. Multistep reaction;

Androst-5-en-3-ol-7,17-dione acetate Specification

The Androst-5-en-3-ol-7,17-dione acetate, with CAS registry number 1449-61-2, belongs to the following product category: Pharmaceutical Raw Materials. It has the systematic name of 7,17-dioxoandrost-5-en-3-yl acetate. And its IUPAC name is (10,13-dimethyl-7,17-dioxo-2,3,4,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-yl) acetate. And the chemical formula of this chemical is C₂₁H₂₈O₄.

Physical properties of Androst-5-en-3-ol-7,17-dione acetate: (1)ACD/LogP: 2.49; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.49; (4)ACD/LogD (pH 7.4): 2.49; (5)ACD/BCF (pH 5.5): 45.56; (6)ACD/BCF (pH 7.4): 45.56; (7)ACD/KOC (pH 5.5): 535.61; (8)ACD/KOC (pH 7.4): 535.61; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 60.44 Å²; (13)Index of Refraction: 1.548; (14)Molar Refractivity: 92.81 cm³; (15)Molar Volume: 291.9 cm³; (16)Polarizability: 36.79×10^-24cm³; (17)Surface Tension: 45.3 dyne/cm; (18)Enthalpy of Vaporization: 74.4 kJ/mol; (19)Vapour Pressure: 2.32E-09 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: CC(=O)OC4CC[C@@]1(C)C(=C\C(=O)[C@H]2[C@@H]3CCC(=O)[C@@]3(C)CC[C@H]12)/C4
(2)InChI: InChI=1/C21H28O4/c1-12(22)25-14-6-8-20(2)13(10-14)11-17(23)19-15-4-5-18(24)21(15,3)9-7-16(19)20/h11,14-16,19H,4-10H2,1-3H3/t14?,15-,16-,19-,20-,21-/m0/s1
(3)InChIKey: VVSMJVQHDZUPIL-FQAVLMBTBQ
(4)Std. InChI: InChI=1S/C21H28O4/c1-12(22)25-14-6-8-20(2)13(10-14)11-17(23)19-15-4-5-18(24)21(15,3)9-7-16(19)20/h11,14-16,19H,4-10H2,1-3H3/t14?,15-,16-,19-,20-,21-/m0/s1
(5)Std. InChIKey: VVSMJVQHDZUPIL-FQAVLMBTSA-N

Product Name

Androst-5-en-3-ol-7,17-dione acetate

Synthetic route

Androst-5-en-3-ol-7,17-dione acetate Specification

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