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853-23-6

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  • Dehydroepiandrosterone acetate/ CAS:853-23-6 /Dehydroepiandrosterone acetate raw material/ high-quality

    Cas No: 853-23-6

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853-23-6 Usage

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 853-23-6 differently. You can refer to the following data:
1. Menopausal syndrome
2. A metabolite of Dehydroepiandrosterone. This mammalian pro-hormone promotes brain and immune function

Flammability and Explosibility

Notclassified

Biological Activity

Dehydroepiandrosterone acetate (DHEA, Androstenolone) is a kind of dehydroepiandrosterone derivatives. DHEA is an endogenous steroid hormone, which is considered to be a natural product/dietary supplement with many proposed benefits to humans.

in vivo

Dehydroisoandrosterone implants increases aggression in a laboratory-based simulated territorial intrusion. Brains of Dehydroisoandrosterone-implanted birds show higher aromatase mRNA expression in the preoptic area (POA) and higher androgen receptor mRNA expression in the periventricular nucleus of the medial striatum (pvMSt) and ventromedial nucleus of the hypothalamus (VMH). The Dehydroisoandrosterone-induced increases in aromatase expression in the POA and androgen receptor expression in the pvMSt are consistent with previously reported seasonal increases in these markers associated with naturally elevated Dehydroisoandrosterone levels. Dehydroisoandrosterone supplementation (10.2 mg/kg) alone significantly increases mice body weight (BW), muscle weight, testosterone level, and glycogen contents (liver and muscle) when compared with SC group.

Check Digit Verification of cas no

The CAS Registry Mumber 853-23-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,5 and 3 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 853-23:
(5*8)+(4*5)+(3*3)+(2*2)+(1*3)=76
76 % 10 = 6
So 853-23-6 is a valid CAS Registry Number.
InChI:InChI=1/C21H30O3/c1-13(22)24-15-8-10-20(2)14(12-15)4-5-16-17-6-7-19(23)21(17,3)11-9-18(16)20/h4,15-18H,5-12H2,1-3H3

853-23-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name Dehydroisoandrosterone 3-acetate

1.2 Other means of identification

Product number -
Other names Dehydroepiandrosteroneacetate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:853-23-6 SDS

853-23-6Synthetic route

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

acetic anhydride
108-24-7

acetic anhydride

prasterone acetate
853-23-6

prasterone acetate

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 0.0111667h; microwave irradiation;100%
With dmap; triethylamine In dichloromethane at 20℃; for 5h;100%
With dmap; triethylamine In dichloromethane at 20℃; for 5h;100%
5α,6α-epoxy-17-oxoandrostan-3β-yl acetate
14545-93-8

5α,6α-epoxy-17-oxoandrostan-3β-yl acetate

prasterone acetate
853-23-6

prasterone acetate

Conditions
ConditionsYield
With iodine; triphenylphosphine In dichloromethane98%
3β-acetoxy-17-cycloethylenedioxy-androst-5-ene
14456-20-3, 17921-59-4

3β-acetoxy-17-cycloethylenedioxy-androst-5-ene

prasterone acetate
853-23-6

prasterone acetate

Conditions
ConditionsYield
With Montmorillonite K 10; water In acetone for 9h; Heating;98%
With silica gel; copper(II) sulfate In chloroform for 5h; Heating;93%
3β,17β-Diacetoxy-androsta-5,16-diene
25256-95-5

3β,17β-Diacetoxy-androsta-5,16-diene

prasterone acetate
853-23-6

prasterone acetate

Conditions
ConditionsYield
With lipase from Candida antarctica In acetonitrile at 30℃; for 3h;98%
3β-acetoxy-17α-hydroxy-5-pregnen-20-one
1863-39-4

3β-acetoxy-17α-hydroxy-5-pregnen-20-one

prasterone acetate
853-23-6

prasterone acetate

Conditions
ConditionsYield
With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide In dichloromethane; acetonitrile for 0.75h;95%
acetyl chloride
75-36-5

acetyl chloride

3-tetrahydropyran-2-yloxy-androst-5-en-17-one
19637-35-5

3-tetrahydropyran-2-yloxy-androst-5-en-17-one

prasterone acetate
853-23-6

prasterone acetate

Conditions
ConditionsYield
In acetone for 5h; Ambient temperature;95%
C24H36O2S2
91414-05-0

C24H36O2S2

A

prasterone acetate
853-23-6

prasterone acetate

B

Acetic acid (2S,4aR,4bS,6aS,12aS,12bR)-4a,6a-dimethyl-2,3,4,4a,4b,5,6,6a,9,10,12,12a,12b,13-tetradecahydro-1H,8H-7,11-dithia-azuleno[2,1-a]phenanthren-2-yl ester
91414-07-2

Acetic acid (2S,4aR,4bS,6aS,12aS,12bR)-4a,6a-dimethyl-2,3,4,4a,4b,5,6,6a,9,10,12,12a,12b,13-tetradecahydro-1H,8H-7,11-dithia-azuleno[2,1-a]phenanthren-2-yl ester

Conditions
ConditionsYield
With Phenylselenyl chloride In dichloromethane at 0℃; for 0.75h;A 6%
B 90%
3β-acetoxy-5β,6β-epoxyandrostan-17-one
6585-68-8

3β-acetoxy-5β,6β-epoxyandrostan-17-one

prasterone acetate
853-23-6

prasterone acetate

Conditions
ConditionsYield
With dimethyl diazomalonate; chloro[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene]copper(I) In toluene for 4h; Reagent/catalyst; Sealed tube; Reflux; stereospecific reaction;85%
With iodine; triphenylphosphine In dichloromethane75%
C29H37NO6
51673-57-5

C29H37NO6

A

prasterone acetate
853-23-6

prasterone acetate

B

3β-hydroxy-13α-methylandrost-5-en-17-one acetate
18462-31-2

3β-hydroxy-13α-methylandrost-5-en-17-one acetate

Conditions
ConditionsYield
In benzene for 5h; Irradiation;A 71%
B 0.7%
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

acetyl chloride
75-36-5

acetyl chloride

prasterone acetate
853-23-6

prasterone acetate

Conditions
ConditionsYield
In toluene for 24h; Reflux;69.3%
C20H30O4S

C20H30O4S

cesium acetate
3396-11-0

cesium acetate

prasterone acetate
853-23-6

prasterone acetate

Conditions
ConditionsYield
With 4-methyl-morpholine; 18-crown-6 ether for 24h; Reflux; Inert atmosphere;64.2%
5-androstene-3β,17β-diol 3-acetate 17-p-toluene-δ-sulfonate
1259-22-9

5-androstene-3β,17β-diol 3-acetate 17-p-toluene-δ-sulfonate

A

prasterone acetate
853-23-6

prasterone acetate

B

3β-acetoxyandrost-5,16-diene
1236-14-2

3β-acetoxyandrost-5,16-diene

C

17α-hydroxyandrost-5-en-3β-yl 3-acetate
100428-85-1

17α-hydroxyandrost-5-en-3β-yl 3-acetate

Conditions
ConditionsYield
With sodium nitrite In dimethyl sulfoxide at 135℃; for 1h;A 17%
B 26%
C 44%
formaldehyd
50-00-0

formaldehyd

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

A

prasterone acetate
853-23-6

prasterone acetate

B

3β-hydroxymethoxy-5-androsten-17-one acetate

3β-hydroxymethoxy-5-androsten-17-one acetate

C

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

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

Conditions
ConditionsYield
With sulfuric acid In dichloromethane; water for 7h; Ambient temperature;A 43%
B 21%
C 17%
C28H35NO4
154592-38-8

C28H35NO4

A

prasterone acetate
853-23-6

prasterone acetate

B

3β-hydroxy-13α-methylandrost-5-en-17-one acetate
18462-31-2

3β-hydroxy-13α-methylandrost-5-en-17-one acetate

C

(3S,8R,9S,10R,14S)-3-Hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-17-one

(3S,8R,9S,10R,14S)-3-Hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-17-one

Conditions
ConditionsYield
With tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) In cyclohexane for 4h;A 36%
B 40%
C 6%
C28H35NO4
154592-38-8

C28H35NO4

A

prasterone acetate
853-23-6

prasterone acetate

B

3β-hydroxy-13α-methylandrost-5-en-17-one acetate
18462-31-2

3β-hydroxy-13α-methylandrost-5-en-17-one acetate

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In cyclohexane for 4h; Heating;A 36%
B 40%
(Z)-3β-acetoxy-17-hydroxyiminoandrost-5-ene
106294-20-6

(Z)-3β-acetoxy-17-hydroxyiminoandrost-5-ene

A

prasterone acetate
853-23-6

prasterone acetate

B

3-acetoxy-17a-aza-17a-homo-androst-5-en-17-one
2232-16-8, 76023-66-0

3-acetoxy-17a-aza-17a-homo-androst-5-en-17-one

Conditions
ConditionsYield
With dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid Mechanism;A 13%
B 16%
pyridine
110-86-1

pyridine

(20S)-3β.17.20-trihydroxy-pregnen-(5)-al-(21)
102707-72-2

(20S)-3β.17.20-trihydroxy-pregnen-(5)-al-(21)

A

prasterone acetate
853-23-6

prasterone acetate

B

17α-hydroxy-3β,21-diacetoxy-5-pregnen-20-one
3517-42-8

17α-hydroxy-3β,21-diacetoxy-5-pregnen-20-one

Conditions
ConditionsYield
at 110℃; und anschliessenden Behandeln mit Acetanhydrid;
pyridine
110-86-1

pyridine

21,21-diphenyl-17βH-pregnene-(5)-triol-(3β,17,21)

21,21-diphenyl-17βH-pregnene-(5)-triol-(3β,17,21)

acetic anhydride
108-24-7

acetic anhydride

A

1,1-Diphenylethylene
530-48-3

1,1-Diphenylethylene

B

prasterone acetate
853-23-6

prasterone acetate

C

acetic acid-(17,21-dihydroxy-21,21-diphenyl-17βH-pregnen-(5)-yl-(3β)-ester)

acetic acid-(17,21-dihydroxy-21,21-diphenyl-17βH-pregnen-(5)-yl-(3β)-ester)

pyridine
110-86-1

pyridine

acetic acid-(17,21-dihydroxy-21,21-diphenyl-17βH-pregnen-(5)-yl-(3β)-ester)

acetic acid-(17,21-dihydroxy-21,21-diphenyl-17βH-pregnen-(5)-yl-(3β)-ester)

acetic anhydride
108-24-7

acetic anhydride

A

1,1-Diphenylethylene
530-48-3

1,1-Diphenylethylene

B

prasterone acetate
853-23-6

prasterone acetate

C

3β-acetoxy-21.21-diphenyl-pregnatriene-(5.16.20)

3β-acetoxy-21.21-diphenyl-pregnatriene-(5.16.20)

Conditions
ConditionsYield
at 134℃;
pyridine
110-86-1

pyridine

3β-acetoxy-20-hydroxyiminopregna-5,16-diene
23549-24-8, 23549-26-0, 2174-13-2

3β-acetoxy-20-hydroxyiminopregna-5,16-diene

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

prasterone acetate
853-23-6

prasterone acetate

Conditions
ConditionsYield
und Behandeln des Reaktionsgemisches mit wss.H2SO4;
pyridine
110-86-1

pyridine

3β-acetoxy-20-hydroxyiminopregna-5,16-diene
23549-24-8, 23549-26-0, 2174-13-2

3β-acetoxy-20-hydroxyiminopregna-5,16-diene

p-acetylaminobenzenesulfonyl chloride
121-60-8

p-acetylaminobenzenesulfonyl chloride

prasterone acetate
853-23-6

prasterone acetate

Conditions
ConditionsYield
und anschliessend mit Eis und wss.H2SO4;
ethanol
64-17-5

ethanol

(3S,8R,9S,10R,13S,14S)-3-Chloro-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-17-one
897-01-8

(3S,8R,9S,10R,13S,14S)-3-Chloro-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-17-one

potassium acetate
127-08-2

potassium acetate

prasterone acetate
853-23-6

prasterone acetate

Conditions
ConditionsYield
at 180 - 200℃;
N-acetylacetamide
625-77-4

N-acetylacetamide

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

prasterone acetate
853-23-6

prasterone acetate

Conditions
ConditionsYield
With toluene-4-sulfonic acid
acetic acid-(17-hydroxy-pregnen-(5)-yn-(20)-yl-(3β)-ester)
130550-34-4

acetic acid-(17-hydroxy-pregnen-(5)-yn-(20)-yl-(3β)-ester)

A

prasterone acetate
853-23-6

prasterone acetate

B

17-hydroxy-3β-acetoxy-21-nor-pregnen-(5)-oic acid-(20)

17-hydroxy-3β-acetoxy-21-nor-pregnen-(5)-oic acid-(20)

Conditions
ConditionsYield
With tetrachloromethane; bromine at -10℃; Einleiten von Ozon (1 Mol) in das Reaktionsgemisch und Behandeln des Reaktionsprodukts mit Aethylacetat, Essigsaeure, Natriumacetat und Zink;
3β-acetoxy-5α,6β-dibromocholestane
514-50-1

3β-acetoxy-5α,6β-dibromocholestane

A

prasterone acetate
853-23-6

prasterone acetate

B

3β-hydroxy-5-cholenoic acid
5255-17-4

3β-hydroxy-5-cholenoic acid

Conditions
ConditionsYield
With chromium(VI) oxide; acetic acid Erwaermen des Reaktionsprodukts mit Zink-Pulver und Essigsaeure und Erwaermen des erhaltenen Reaktionsprodukts mit methanol. Kalilauge;
With chromium(VI) oxide; acetic acid Erwaermen des Reaktionsprodukts mit Zink-Pulver und Essigsaeure und Erwaermen des erhaltenen Reaktionsprodukts mit wss. Natronlauge;
3β-hydroxy-17.17a-seco-D-homo-androstene-(5)-dioic acid-(17.17a)
2099-39-0

3β-hydroxy-17.17a-seco-D-homo-androstene-(5)-dioic acid-(17.17a)

acetic anhydride
108-24-7

acetic anhydride

prasterone acetate
853-23-6

prasterone acetate

Conditions
ConditionsYield
Erhitzen auf Siedetemperatur und kurzes Erhitzen des Reaktionsprodukts unter vermindertem Druck auf 250grad;
Erwaermen des Reaktionsprodukts unter 10 Torr auf 250grad;
3β-bromoandrost-5-en-17-one
51104-94-0

3β-bromoandrost-5-en-17-one

silver(I) acetate
563-63-3

silver(I) acetate

acetic acid
64-19-7

acetic acid

prasterone acetate
853-23-6

prasterone acetate

acetic acid-(17,21-dihydroxy-21,21-diphenyl-17βH-pregnen-(5)-yl-(3β)-ester)

acetic acid-(17,21-dihydroxy-21,21-diphenyl-17βH-pregnen-(5)-yl-(3β)-ester)

acetic acid
64-19-7

acetic acid

A

1,1-Diphenylethylene
530-48-3

1,1-Diphenylethylene

B

prasterone acetate
853-23-6

prasterone acetate

(3S,8R,9S,10R,13S,14S)-3-Chloro-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-17-one
897-01-8

(3S,8R,9S,10R,13S,14S)-3-Chloro-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-17-one

potassium acetate
127-08-2

potassium acetate

acetic acid
64-19-7

acetic acid

prasterone acetate
853-23-6

prasterone acetate

Conditions
ConditionsYield
at 180 - 200℃;
3β-acetoxy-pregna-5,16-dien-20-on-(O-acetyl oxime )
5040-79-9

3β-acetoxy-pregna-5,16-dien-20-on-(O-acetyl oxime )

trifluoroborane diethyl ether
109-63-7

trifluoroborane diethyl ether

benzene
71-43-2

benzene

prasterone acetate
853-23-6

prasterone acetate

prasterone acetate
853-23-6

prasterone acetate

androstenediol-3-acetate
1639-43-6

androstenediol-3-acetate

Conditions
ConditionsYield
With L-Selectride In tetrahydrofuran at 0℃; for 0.5h;100%
With sodium tetrahydroborate In methanol; dichloromethane; ethyl acetate for 1h;99%
With sodium tetrahydroborate; Dowex1-x8 In tetrahydrofuran for 7.5h; Heating;97%
prasterone acetate
853-23-6

prasterone acetate

3β-acetoxy-androst-5-en-17-one oxime
84368-89-8, 106294-20-6, 119907-02-7, 21063-30-9

3β-acetoxy-androst-5-en-17-one oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In methanol for 1.5h; Reflux;99.2%
With hydroxylamine hydrochloride; sodium acetate In ethanol; water for 5h; Reflux;98.1%
With pyridine; hydroxylamine hydrochloride at 20℃; Inert atmosphere;79%
Conditions
ConditionsYield
With diisobutylaluminium hydride; nickel dichloride In dichloromethane; toluene at -78℃; for 0.25h; Inert atmosphere;99%
Stage #1: prasterone acetate With potassium borohydride In methanol at 36℃; for 0.666667h;
Stage #2: In methanol at 20℃; for 1h; Further stages.;
95%
prasterone acetate
853-23-6

prasterone acetate

3β-hydroxy-16-hydroxyiminoandrost-5-en-17-one
19321-67-6, 40962-87-6, 99094-86-7, 21242-37-5

3β-hydroxy-16-hydroxyiminoandrost-5-en-17-one

Conditions
ConditionsYield
With tert.-butylnitrite; potassium tert-butylate In tert-butyl alcohol at 20℃; for 24h;99%
prasterone acetate
853-23-6

prasterone acetate

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
With sodium hydroxide In methanol98.54%
With methanol; sodium hydroxide at 40℃; for 4h; Inert atmosphere;94.8%
With potassium hydroxide In ethanol
prasterone acetate
853-23-6

prasterone acetate

androst-5-en-3β-ol
1476-64-8

androst-5-en-3β-ol

Conditions
ConditionsYield
Stage #1: prasterone acetate With hydrazine hydrate In 2-ethoxy-ethanol Wolff-Kishner reduction; Inert atmosphere; Heating;
Stage #2: With potassium hydroxide In 2-ethoxy-ethanol at 136℃; for 3h; Wolff-Kishner reduction;
98%
With potassium hydroxide; hydrazine hydrate In diethylene glycol 1.) 140 deg C, 30 min, 2.) 195 deg C, 2 h;69.8%
prasterone acetate
853-23-6

prasterone acetate

ethylene glycol
107-21-1

ethylene glycol

3β-acetoxy-17-cycloethylenedioxy-androst-5-ene
14456-20-3, 17921-59-4

3β-acetoxy-17-cycloethylenedioxy-androst-5-ene

Conditions
ConditionsYield
With toluene-4-sulfonic acid In various solvent(s) at 90℃; for 1h;98%
With toluene-4-sulfonic acid; orthoformic acid triethyl ester for 2h; Reflux;97%
With montmorillonite K-10 In benzene for 7h; Heating;95%
prasterone acetate
853-23-6

prasterone acetate

3α,6β-dibromo-3β-acetoxyandrostan-17-one
53274-78-5

3α,6β-dibromo-3β-acetoxyandrostan-17-one

Conditions
ConditionsYield
With bromine In tetrachloromethane for 0.5h;97%
With tetrachloromethane; bromine at 2 - 5℃;
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

prasterone acetate
853-23-6

prasterone acetate

ethyl diazo<17ξ-hydroxy-3β-acetoxy-5-androstene-17ξ-yl>acetate

ethyl diazo<17ξ-hydroxy-3β-acetoxy-5-androstene-17ξ-yl>acetate

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.75h;97%
prasterone acetate
853-23-6

prasterone acetate

(aminooxy)acetic acid hemihydrochloride
2921-14-4, 7776-18-3, 20295-82-3

(aminooxy)acetic acid hemihydrochloride

(17E)-3β-acetoxyandrost-5-en-17-one (O-carboxymethyl)oxime
177285-06-2

(17E)-3β-acetoxyandrost-5-en-17-one (O-carboxymethyl)oxime

Conditions
ConditionsYield
In pyridine at 60℃; for 6h;97%
prasterone acetate
853-23-6

prasterone acetate

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

3β-acetoxy-5β,6β-epoxyandrostan-17-one

Conditions
ConditionsYield
With dinitrogen monoxide; dioxo(tetramesitylporphyrinato)ruthenium(VI) In chlorobenzene at 140℃; under 7600 Torr;97%
With dinitrogen monoxide; dioxo(tetramesitylporphyrinato)ruthenium(VI) In chlorobenzene at 140℃; under 7500.6 Torr; for 5h;97%
With iron(III) sulfate; potassium permanganate In dichloromethane; water; tert-butyl alcohol for 0.3h; Ambient temperature;93%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

prasterone acetate
853-23-6

prasterone acetate

C22H31F3O5S

C22H31F3O5S

Conditions
ConditionsYield
With dmap; sodium carbonate In dichloromethane at -10 - -5℃; Reagent/catalyst; Inert atmosphere;96.6%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

prasterone acetate
853-23-6

prasterone acetate

3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
115375-60-5

3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate

Conditions
ConditionsYield
Stage #1: prasterone acetate With potassium carbonate In toluene; benzene at 25℃; for 0.5h;
Stage #2: trifluoromethylsulfonic anhydride In toluene; benzene at -18 - -15℃; for 20.33h; Reagent/catalyst; Solvent; Temperature;
96%
Stage #1: prasterone acetate With potassium carbonate In toluene; benzene at 25℃; for 0.5h;
Stage #2: trifluoromethylsulfonic anhydride In toluene; benzene at -18 - -15℃; for 20.33h;
96%
Stage #1: trifluoromethylsulfonic anhydride; prasterone acetate In dichloromethane at 20℃; for 0.0833333h;
Stage #2: With 2-methoxypyridine In dichloromethane at 20 - 30℃; for 2.5h; Reagent/catalyst;
93%
prasterone acetate
853-23-6

prasterone acetate

malononitrile
109-77-3

malononitrile

(3S)-17-(dicyanomethylidene)androst-5-en-3-yl acetate
83035-78-3

(3S)-17-(dicyanomethylidene)androst-5-en-3-yl acetate

Conditions
ConditionsYield
With ammonium acetate In ethanol for 3h; Reflux;95%
With ammonium acetate In ethanol for 3h; Reflux;95%
With ammonium acetate In acetic acid; toluene for 48h; Knoevenagel Condensation; Dean-Stark; Reflux;83%
tert-Butyl peroxybenzoate
614-45-9

tert-Butyl peroxybenzoate

prasterone acetate
853-23-6

prasterone acetate

Benzoic acid (3S,7S,8R,9S,10R,13S,14S)-3-acetoxy-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-7-yl ester

Benzoic acid (3S,7S,8R,9S,10R,13S,14S)-3-acetoxy-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-7-yl ester

Conditions
ConditionsYield
Stage #1: prasterone acetate With copper(I) bromide In dichloromethane for 0.25h; Heating;
Stage #2: tert-Butyl peroxybenzoate In dichloromethane Heating;
95%
prasterone acetate
853-23-6

prasterone acetate

benzenesufonyl hydrazide
80-17-1

benzenesufonyl hydrazide

A

5-dehydroepiandrosterone benzenesulfonyl hydrazone

5-dehydroepiandrosterone benzenesulfonyl hydrazone

B

3-acetyl-5-dehydroepiandrosterone benzenesulfonyl hydrazone

3-acetyl-5-dehydroepiandrosterone benzenesulfonyl hydrazone

Conditions
ConditionsYield
With toluene-4-sulfonic acid In tetrahydrofuran Inert atmosphere; Reflux;A n/a
B 94%
prasterone acetate
853-23-6

prasterone acetate

benzenesufonyl hydrazide
80-17-1

benzenesufonyl hydrazide

3-acetyl-5-dehydroepiandrosterone benzenesulfonyl hydrazone

3-acetyl-5-dehydroepiandrosterone benzenesulfonyl hydrazone

Conditions
ConditionsYield
With toluene-4-sulfonic acid In tetrahydrofuran for 3h; Inert atmosphere;94%
With toluene-4-sulfonic acid In tetrahydrofuran Inert atmosphere; Reflux;
prasterone acetate
853-23-6

prasterone acetate

methyl 2-cyanoacetate
105-34-0

methyl 2-cyanoacetate

methyl (E)-2-[(3S)-3-acetoxyandrost-5-en-17-ylidene]-2-cyanoacetate
1588771-90-7

methyl (E)-2-[(3S)-3-acetoxyandrost-5-en-17-ylidene]-2-cyanoacetate

Conditions
ConditionsYield
With ammonium acetate In acetic acid; toluene for 48h; Knoevenagel Condensation; Dean-Stark; Reflux;94%
With ammonium acetate; acetic acid In toluene for 48h; Knoevenagel Condensation; Dean-Stark; Reflux;94%
prasterone acetate
853-23-6

prasterone acetate

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

3-O-acetyl-7-oxo-dehydroepiandrosterone

Conditions
ConditionsYield
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%
1-(2-nitrophenyl)ethane-1,2-diol
51673-59-7

1-(2-nitrophenyl)ethane-1,2-diol

prasterone acetate
853-23-6

prasterone acetate

C29H37NO6
51673-57-5

C29H37NO6

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 3h; Heating; in the dark;92%
prasterone acetate
853-23-6

prasterone acetate

3β-hydroxy-16α-bromoandrost-5-ene-17-one
1093-91-0

3β-hydroxy-16α-bromoandrost-5-ene-17-one

Conditions
ConditionsYield
With copper(ll) bromide In methanol for 8h; Heating;91%
With copper(ll) bromide In methanol Heating;91%
With copper(ll) bromide In methanol70%
prasterone acetate
853-23-6

prasterone acetate

A

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

3β-acetoxy-5β,6β-epoxyandrostan-17-one

B

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

5α,6α-epoxy-17-oxoandrostan-3β-yl acetate

Conditions
ConditionsYield
With potassium permanganate; copper(II) sulfate In dichloromethane; water; tert-butyl alcohol for 2h; Yields of byproduct given;A 90%
B n/a
With oxygen; trans-dioxo(5,10,15,20-tetramesitylporphirinato)ruthenium(VI) In benzene at 20℃; for 168h; Title compound not separated from byproducts;A 73%
B n/a
With potassium permanganate; acetic acid
prasterone acetate
853-23-6

prasterone acetate

benzaldehyde
100-52-7

benzaldehyde

thiourea
17356-08-0

thiourea

3β-acetoxy-3',4'-dihydropyrimidino[6',5':16,17]androst-5-ene-2'(1'H)-thione
1408324-43-5

3β-acetoxy-3',4'-dihydropyrimidino[6',5':16,17]androst-5-ene-2'(1'H)-thione

Conditions
ConditionsYield
With sodium ethanolate In isopropyl alcohol at 20℃; for 0.25h; Sonication;90%

853-23-6Relevant articles and documents

The effects of DHEA, 3β-hydroxy-5α-androstane-6,17-dione, and 7-amino-DHEA analogues on short term and long term memory in the mouse

Bazin, Marc-Antoine,Kihel, La?la El,Boulouard, Michel,Bou?t, Valentine,Rault, Sylvain

, p. 931 - 937 (2009)

Neurosteroids have been reported to modulate memory processes in rodents. Three analogues of dehydroepiandrosterone (DHEA), two of them previously described (7β-aminoDHEA and 7β-amino-17-ethylenedioxy-DHEA), and a new one (3β-hydroxy-5α-androstane-6,17-dione) were synthesized, and their effects were evaluated on memory. This study examined their effects on long term and short term memory in male (6 weeks old) NMRI mice in comparison with the reference drug. Long term memory was assessed using the passive avoidance task and short term memory (spatial working memory) using the spontaneous alternation task in a Y maze. Moreover, the effects of DHEA and its analogues on spontaneous locomotion were measured. In all tests, DHEA and analogues were injected at three equimolar doses (0.300-1.350-6.075 μM/kg). DHEA and its three analogues administered immediately post-training at the highest doses (6.075 μM/kg, s.c.) improved retention in passive avoidance test. Without effect per se in the spatial working memory task, the four compounds failed to reverse scopolamine (1 mg/kg, i.p.)-induced deficit in spontaneous alternation. These data suggested an action of DHEA and analogues in consolidation of long term memory particularly when emotional components are implied. Moreover, data indicated that pharmacological modulation of DHEA as performed in this study provides derivatives giving the same mnemonic profile than reference molecule.

Facile synthesis of novel D-ring modified steroidal dienamides via rearrangement of 2H-pyrans

Yu, Bin,Zhang, En,Sun, Xiao-Nan,Ren, Jing-Li,Fang, Yuan,Zhang, Bao-Le,Yu, De-Quan,Liu, Hong-Min

, p. 494 - 499 (2013)

A simple and practical method for synthesis of the D-ring modified steroidal dienamides (4a-k) from the steroidal α,α-dicyanoalkene 3 and aldehydes via vinylogous aldol reaction was first reported. By using NaOAc as a base, the desired products were obtained in moderate to good yields in ethanol under mild conditions. All the synthesized steroidal dienamides are new and are currently being evaluated for their biological activities.

Synthesis of steroid compounds containing a pyridazinone moiety

Cherkalin,Kolobov,Chernoburova,Shchetinina,Zavarzin

, p. 2144 - 2147 (2018)

The reaction of 17-ketosteroids and glyoxylic acid followed by treatment with hydrazine affords steroid compounds condensed in the 16 and 17 positions with the pyridazin-3(2H)- one ring.

Preparation method of 3beta-acetoxyandrostane-5-ene-17-one

-

Paragraph 0019; 0056-0057, (2021/02/24)

The invention discloses a method for preparationof 3beta-acetoxyandrostane-5-ene-17-one by utilizing androstane-3-beta hydroxyl-17-one-6alpha-boric acid separated from androstane-5-ene-17-one chemicalreduction reaction solid waste through the four steps of reactions of esterification, oxidation, sulfonic acid esterification and elimination. According to the method, the steroid solid waste can beeffectively recycled, the synthesis method is efficient, the reaction conditions are mild, and the cost of related products is correspondingly reduced while the environmental pollution is reduced.

Novel steroidal 5α,8α-endoperoxide derivatives with semicarbazone/thiosemicarbazone side-chain as apoptotic inducers through an intrinsic apoptosis pathway: Design, synthesis and biological studies

Bu, Ming,Liu, Lei,Ma, Liwei,Wang, Haijun,Wang, Jing,Zhang, Song

, (2020/03/17)

A series of novel steroidal 5α,8α-endoperoxide derivatives bearing semicarbazone (7a-g) or thiosemicarbazone (7h-k) side chain were designed, synthesized and evaluated for their cytotoxicities in four human cancer cell lines (HepG2, HCT-116, MCF-7, and A549) using the MTT assay in vitro. The results showed that compound 7j exhibited significant cytotoxic activity against HepG2 cells (IC50 = 3.52 μM), being more potent than ergosterol peroxide. Further cellular mechanism studies in HepG2 cells indicated that compound 7j triggered the mitochondrial-mediated apoptosis by decreasing mitochondrial membrane potential (MMP), which was associated with up-regulation of Bax, down-regulation of Bcl-2, activation levels of the caspase cascade, and formation of reactive oxygen species (ROS). The above findings indicated that compound 7j may be used as a promising skeleton for antitumor agents with improved efficacy.

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