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53-43-0

Basic Information
CAS No.: 53-43-0
Name: Dehydroepiandrosterone
Molecular Structure:
Molecular Structure of 53-43-0 (Dehydroepiandrosterone)
Formula: C19H28O2
Molecular Weight: 288.47
Synonyms: (3-beta)-3-Hydroxyandrost-5-en-17-one;17-Hormoforin;5, 6-Dehydroisoandrostorone;EPA Pesticide Chemical Code 126510;Andrestenol;Prasterone [INN];Deandros;Prasteronum [INN-Latin];
EINECS: 200-175-5
Density: 1.12 g/cm3
Melting Point: 149-151 °C(lit.)
Boiling Point: 426.7 °C at 760 mmHg
Flash Point: 182.1 °C
Solubility: 21.8mg/L(23.5 oC)
Appearance: white fine crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-24/25
Transport Information:
PSA: 37.30000
LogP: 3.87920
Synthetic route
853-23-6

prasterone acetate

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
1028084-93-6

(1aR,3aR,3bS,5aS,8aS,8bR,10aR)-10-Hydroxy-3a,5a-dimethyl-tetradecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-one

53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
With Me3SiN=CMe(1+)*BF4(1-); water In acetonitrile96%
24357-31-1, 58691-91-1

Acetic acid (1aR,3aR,3bS,5aS,8aS,8bR,10aR)-3a,5a-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-10-yl ester

53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
With Me3SiN=CMe(1+)*BF4(1-); water In acetonitrile96%
327622-68-4

(17Ξ)-spiro[androst-5-en-17,2'-[1,3]oxathiolan]-3β-ol

53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
With N-Bromosuccinimide; water In acetone at 20℃; for 8h; Hydrolysis;88%
1310361-06-8

3β-[2-(triphenylsilyl)ethoxycarbonyloxy]androst-5-en-17-one

53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride; cesium fluoride In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;88%
81481-38-1

5-androsten-3β,17α-diol-17-carboxylic acid

53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
With sodium hydroxide; sodium hypochlorite In diethyl ether 1.) 0 deg C -> room temperature, 2.) room temperature, 3 h;85%
63-05-8

Androstenedione

53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
Stage #1: Androstenedione With titanium(IV) oxide; platinum In toluene at 100℃; for 3h;
Stage #2: With hydrogen In toluene under 15001.5 Torr; for 8h; Temperature; Reagent/catalyst; Pressure;
85%
Multi-step reaction with 2 steps
1.1: potassium tert-butylate / tert-butyl alcohol / 1.5 h / 35 - 40 °C / Inert atmosphere
1.2: 20 - 25 °C
2.1: NADP; magnesium(II) chloride hexahydrate; alpha-D-glucopyranose; NAD+ / 2-methyltetrahydrofuran; aq. phosphate buffer / 20 - 32 °C / Enzymatic reaction
View Scheme
Multi-step reaction with 2 steps
1: potassium tert-butylate / tert-butyl alcohol / 1 h / 30 - 35 °C / Inert atmosphere
2: D-glucose; NAD; glucose dehydrogenase (CDX-901)_; ketoreductase from Sphingomonas wittichii; potassium carbonate / ethyl acetate; aq. phosphate buffer / 21 h / 32.5 °C / pH 6.3 - 6.5 / Inert atmosphere; Enzymatic reaction
View Scheme
Multi-step reaction with 4 steps
1: aluminum (III) chloride; 5-sulfosalicylic Acid / 5 h / 20 - 30 °C / Inert atmosphere; Large scale
2: orthoformic acid triethyl ester; boron trifluoride diethyl etherate / dichloromethane / 5 h / 20 - 30 °C / Inert atmosphere
3: calcium borohydride / dichloromethane / 15 h / -20 - -15 °C
4: toluene-4-sulfonic acid / acetone; water / 1 h / 45 - 50 °C / Inert atmosphere
View Scheme
76920-40-6

17-oxo-androst-5-en-3β-yl Se-phenyl selenocarbonate

A

53-43-0

dehydroepiandrosterone

B

29163-23-3

3β-formyl-oxy-5-androsten-17-one

C

25824-80-0

5-androsten-17-one

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene at 80℃;A 9%
B 76%
C 5%
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In 1,3,5-trimethyl-benzene at 164℃;A 10%
B 28%
C 62%
19637-35-5

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

53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
With silica gel; copper(II) sulfate In dichloromethane for 24h; Heating;70%
23549-24-8, 23549-26-0, 2174-13-2

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

53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
Stage #1: 3β-acetoxy-20-hydroxyiminopregna-5,16-diene With pyridine; trichlorophosphate at 0 - 20℃; for 3h; Inert atmosphere;
Stage #2: With methanol; sodium hydroxide for 12h; Reflux;
64%
Stage #1: 3β-acetoxy-20-hydroxyiminopregna-5,16-diene With pyridine; trichlorophosphate In toluene at 10 - 20℃; for 4h; Bechmanns' reaction;
Stage #2: With potassium hydroxide In methanol Heating;
51.8%
With pyridine; trichlorophosphate at -5℃; Beckmann rearrangement;
Multi-step reaction with 2 steps
1: phosphorus (III) oxychloride
2: potassium hydroxide / methanol
View Scheme
17134-39-3

16α-iodo-3β-hydroxy-5-androsten-17-one

A

53-43-0

dehydroepiandrosterone

B

1232-73-1

16α-hydroxy dehydroepiandrosterone

Conditions
ConditionsYield
With sodium hydroxide In pyridine; water for 1h;A 20%
B 60%
With sodium hydroxide In pyridine; water for 1h;A 20%
B 60%
With sodium hydroxide In pyridine; water for 1h; Mechanism; var. of NaOH conc. and time;A 20%
B 60%

Trifluoro-methanesulfonic 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-yl ester

A

53-43-0

dehydroepiandrosterone

B

66147-28-2

bis(3β-androst-5-en-17-one) ether

Conditions
ConditionsYield
With 1,2,2,6,6-pentamethylpiperidine In water Heating;A 60%
B 40%

3β-O-(tetrahydropyranyl)-17-cycloethylenedioxy-androst-5-ene

A

53-43-0

dehydroepiandrosterone

B

7745-40-6, 14456-21-4

3β-hydroxy-17,17-ethylenedioxo-5-androstene

C

19637-35-5

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

Conditions
ConditionsYield
With silica gel; copper(II) sulfate In benzene at 25℃; for 40h;A 17%
B 59%
C 2%
With silica gel; copper(II) sulfate In chloroform at 25℃; for 40h;A 51%
B 6%
C 30%

C28H47NO2

53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 0.166667h;46%
34837-55-3

Phenylselenyl bromide

63015-10-1, 77059-27-9

androstenone hydrazone

A

53-43-0

dehydroepiandrosterone

B

114474-49-6

17-bromo-3β-hydroxy-17-selenophenylandrost-5-ene

C

91414-16-3

3β-hydroxy-17-phenylselenoandrosta-5,16-diene

Conditions
ConditionsYield
With pyridine In tetrahydrofuranA 45%
B 8%
C 20%
1259-22-9

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

A

53-43-0

dehydroepiandrosterone

B

1963-03-7

androst-5-ene-3β,17α-diol

C

82309-44-2

17β-methyl-18-norandrosta-5,13-diene-3β-ol

23930-65-6

17-methyl-18-norandrosta-5,13(17)-diene-3β-ol

Conditions
ConditionsYield
With potassium acetate In dimethyl sulfoxide at 100℃; for 6h;A 25%
B 41%
C n/a
D n/a

17-(N-2-pyridylmethyl)imino-3β-hydroxy-androst-5-ene

A

53-43-0

dehydroepiandrosterone

B

828938-19-8

(-)-3β,12β-dihydroxyandrost-5-ene-17-one

Conditions
ConditionsYield
Multistep reaction;A 22%
B 35%
57-88-5

cholesterol

A

53-43-0

dehydroepiandrosterone

B

63-05-8

Androstenedione

Conditions
ConditionsYield
With [2,2]bipyridinyl; Cephalosporium longisporum; Micrococcus sp; Pseudomonas stutzeri at 29℃; for 72h;A 27%
B 6%

17-(N-2-pyridylmethyl)imino-3β-hydroxy-androst-5-ene

A

53-43-0

dehydroepiandrosterone

B

12β-chloro-3β-hydroxy-androst-5-en-17-one

C

828938-19-8

(-)-3β,12β-dihydroxyandrost-5-ene-17-one

Conditions
ConditionsYield
Multistep reaction;A 21%
B 19%
C 25%
145-13-1

Pregnenolone

A

53-43-0

dehydroepiandrosterone

B

34069-59-5

17α-Hydroperoxy-5-pregnen-3β-ol-20-on

Conditions
ConditionsYield
With 18-crown-6 ether In tetrahydrofuran; benzene at 18℃; under 760 Torr; for 24h;A 23%
B 9%
Conditions
ConditionsYield
With Gelasinospora retispora GRK002 In methanol; water at 34℃; for 336h; pH=5; Microbiological reaction;A 23%
B 18%
C 11%
145-13-1

Pregnenolone

A

53-43-0

dehydroepiandrosterone

B

387-79-1

17-Hydroxypregnenolone

Conditions
ConditionsYield
With potassium phosphate buffer; α-D-glucose 6-phosphate; NADP; phosphatidylcholine Mechanism; pig 17α-hydroxylase-17,20-lyase, NADPH-cytochrome-P-450-reductase, glucose-6-phosphate dehydrogenase, pH 7.2; also in the presence of cytochrome b5 or bovine tests microsomes; also 3β-hydroxyandrost-5-ene-17β-carbaldehyde;A 16%
B 21%
57-88-5

cholesterol

53-43-0

dehydroepiandrosterone

83-46-5

β-sitosterol

53-43-0

dehydroepiandrosterone

651-48-9

dehydroepiandrosterone sulfate

A

53-43-0

dehydroepiandrosterone

B

663-39-8, 24357-32-2, 57236-38-1, 118013-84-6

6β-hydroxy-3α,5-cycloandrostan-17-one

Conditions
ConditionsYield
Ausbeute in gepufferten wss. Loesungen (pH 1.2-6.8);
571-36-8

5-androstenedione

A

53-43-0

dehydroepiandrosterone

B

2283-82-1

3α-hydroxy-androst-5-en-17-one

Conditions
ConditionsYield
With ethanol; nickel Hydrogenation;
83205-52-1, 2080-86-6

3β-benzoyloxy-androst-5-en-17-one

53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
With potassium hydroxide
With potassium hydroxide
4350-66-7

17β-Aminoandrost-5-en-3β-ol

53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
With diethyl ether; hypochloric acid; sodium sulfate at 0℃; Erwaermen des Reaktionsprodukts mit Natriumaethylat und Aethanol und Behandeln des Reaktionsloesung mit wss.H2SO4;
35060-03-8

3β,17-dihydroxy-androst-5-ene-17α-carbonitrile

53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
unter vermindertem Druck;
at 110 - 120℃;
60446-55-1

3β-acetoxy-20-methyl-pregnadiene-(5,17(20))

53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
With chloroform; bromine anschliessendes Behandeln mit Ozon; Erhitzen des erhaltenen Reaktionsprodukts mit Zink-Pulver und Essigsaeure und Hydrolysieren des isolierten 3β-Acetoxy-androsten-(5)-ons-(17);
With potassium permanganate; acetic acid at 50℃; Erhitzen des erhaltenen Reaktionsprodukts mit Zink-Pulver und Essigsaeure und Hydrolysieren des isolierten 3β-Acetoxy-androsten-(5)-ons-(17);
64-18-6

formic acid

53-43-0

dehydroepiandrosterone

29163-23-3

3β-formyl-oxy-5-androsten-17-one

Conditions
ConditionsYield
In water for 19h;100%
at 20 - 25℃; for 4h;100%
for 5h; Reflux;89.3%
for 5h; Reflux;
53-43-0

dehydroepiandrosterone

481-29-8

Epiandrosterone

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In ethanol at 20℃; under 2068.65 Torr; Inert atmosphere;100%
With palladium on activated charcoal; hydrogen In ethanol under 2068.65 Torr;100%
With palladium 10% on activated carbon; hydrogen In ethanol at 40℃; under 2068.65 Torr; for 12h;99%
53-43-0

dehydroepiandrosterone

108-24-7

acetic anhydride

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%
53-43-0

dehydroepiandrosterone

107-21-1

ethylene glycol

7745-40-6, 14456-21-4

3β-hydroxy-17,17-ethylenedioxo-5-androstene

Conditions
ConditionsYield
With camphor-10-sulfonic acid In toluene at 111℃;100%
With toluene-4-sulfonic acid In benzene for 4.5h; Heating;99%
With camphor-10-sulfonic acid In cyclohexane for 20h; Reflux;99%
53-43-0

dehydroepiandrosterone

18162-48-6

tert-butyldimethylsilyl chloride

42151-23-5

(3S)-3-tert-butyldimethylsilyloxyandrost-5-en-17-one

Conditions
ConditionsYield
With dmap In dichloromethane 1.) 0 deg C, 1 h, 2.) room temperature, 16 h;100%
With dmap; triethylamine In dichloromethane at 20℃; for 15h;100%
With 1H-imidazole In dichloromethane at 25℃; for 12h;99%
53-43-0

dehydroepiandrosterone

1609-47-8

diethyl dicarbonate

86270-42-0

3β-ethoxycarbonyloxyandrost-5-en-17-one

Conditions
ConditionsYield
for 0.5h; Heating;100%
53-43-0

dehydroepiandrosterone

58479-61-1

tert-butylchlorodiphenylsilane

191677-71-1

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

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide for 120h; Ambient temperature;100%
With impramine99%
With 1H-imidazole In dichloromethane at 0 - 20℃; for 5h;98%
75-77-4

chloro-trimethyl-silane

53-43-0

dehydroepiandrosterone

3747-91-9

PdCl2(PPh3)2

Conditions
ConditionsYield
With pyridine In N,N-dimethyl-formamide at 0 - 20℃; for 2.16667h; Inert atmosphere;100%
With triethylamine In tetrahydrofuran at 20℃;97%
Stage #1: dehydroepiandrosterone With 1H-imidazole In dichloromethane at 20 - 30℃; for 0.0833333h;
Stage #2: chloro-trimethyl-silane In dichloromethane at 20 - 30℃; for 2h; Reagent/catalyst;
81.6%
53-43-0

dehydroepiandrosterone

126-30-7

2,2-Dimethyl-1,3-propanediol

(3S,8R,9S,10R,13S,14S)-5',5',10,13-tetramethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxan]-3-ol

Conditions
ConditionsYield
With camphor-10-sulfonic acid In cyclohexane at 85℃; for 16h; Dean-Stark;99.8%
53-43-0

dehydroepiandrosterone

63015-10-1

dehydroepiandrosterone-17-hydrazone

Conditions
ConditionsYield
With barium sulfate; hydrazine hydrate In ethanol; water at 20 - 30℃; for 12h; Large scale;99.2%
With sulfuric acid; hydrazine hydrate In ethanol at 20℃; for 40h;98.7%
Stage #1: dehydroepiandrosterone With hydrazine hydrate In ethanol at 35℃;
Stage #2: With hydrazinium sulfate In ethanol at 35℃; for 20h;
98.5%
53-43-0

dehydroepiandrosterone

107-30-2

chloromethyl methyl ether

18000-76-5

(3β)-3-(methoxymethoxy)-androst-5-en-17-one

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 3.5h;99%
With N,N-dimethyl-aniline In dichloromethane; benzene for 12h; Ambient temperature;75%
1460-16-8

cycloheptanoic acid

53-43-0

dehydroepiandrosterone

1470067-56-1

17-oxaandrost-5-ene-3β-yl cycloheptanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; for 2h;99%
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; for 2h;88%
With dmap; dicyclohexyl-carbodiimide In chloroform Steglich Esterification;
With dmap; dicyclohexyl-carbodiimide
53-43-0

dehydroepiandrosterone

124-63-0

methanesulfonyl chloride

25810-70-2

androst-5-en-3β-ol-17-one mesylate

Conditions
ConditionsYield
With pyridine at 20 - 25℃; for 20h; Inert atmosphere;98.4%
With pyridine at 20℃; for 24h;76%
53-43-0

dehydroepiandrosterone

3282-30-2

pivaloyl chloride

158300-47-1

(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-ylpivalate

Conditions
ConditionsYield
With pyridine at 10 - 28℃; for 16.5h;98.1%
With pyridine at 85℃; for 14h;91%
With pyridine; dmap at 0℃; for 4h;5.83 g
53-43-0

dehydroepiandrosterone

1476-64-8

androst-5-en-3β-ol

Conditions
ConditionsYield
With potassium hydroxide; hydrazine hydrate In diethylene glycol a) 120 deg C, 1 h, b) 230 deg C, 3.5 h;98%
Stage #1: dehydroepiandrosterone With hydrazine hydrate In diethylene glycol at 130℃; for 2h; Wolff-Kishner Reduction;
Stage #2: With potassium hydroxide In diethylene glycol at 210℃; for 4h;
Stage #3: With sulfuric acid In water; diethylene glycol
95.8%
With chloro-trimethyl-silane; zinc In methanol; dichloromethane at 0 - 20℃; for 18h; Clemmensen Reduction;75%
53-43-0

dehydroepiandrosterone

100-52-7

benzaldehyde

17243-87-7, 74708-33-1

16-benzylidene-17-oxo-5-androsten-3β-ol

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 1h;98%
With methanol; potassium hydrogencarbonate
With Aliquat 336; sodium carbonate In water at 80℃; for 2.5h; Aldol Condensation;
With potassium fluoride on basic alumina In ethanol for 1h; Claisen-Schmidt Condensation; Reflux;
53-43-0

dehydroepiandrosterone

98-88-4

benzoyl chloride

83205-52-1, 2080-86-6

3β-benzoyloxy-androst-5-en-17-one

Conditions
ConditionsYield
With pyridine at 10 - 25℃; Reagent/catalyst; Temperature;98%
With tetramethylurea at 70 - 75℃; for 3h;78%
With pyridine at 20℃; for 12h;76%
With pyridine
53-43-0

dehydroepiandrosterone

96-83-3

iopanoic acid

83172-20-7

dehydroepiandrosterone iopanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature;98%
53-43-0

dehydroepiandrosterone

1093-91-0

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

Conditions
ConditionsYield
With copper(ll) bromide In methanol for 12h; Heating;98%
With copper(ll) bromide In methanol at 70℃; for 12h;97%
With copper(I) bromide In methanol; benzene for 4h; Heating / reflux;62.77%
53-43-0

dehydroepiandrosterone

107-11-9

1-amino-2-propene

1322574-37-7

17β-allylamino-3β-hydroxyandrost-5-ene

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran; 1,2-dichloro-ethane at 20℃;98%
With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran; 1,2-dichloro-ethane for 48h;
3721-95-7

Cyclobutanecarboxylic acid

53-43-0

dehydroepiandrosterone

1345406-89-4

3β-cyclobutylcarbonyloxy-5-androsten-17-one

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; for 2h;98%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h;90.4%
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; for 2h;84%
With dmap; dicyclohexyl-carbodiimide In chloroform Steglich Esterification;
With dmap; dicyclohexyl-carbodiimide
53-43-0

dehydroepiandrosterone

459-57-4

4-fluorobenzaldehyde

1428382-54-0

(E)-16-(4-fluorophenyl)methylidene-trans-dehydroandrosterone

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 1h;98%
With potassium fluoride on basic alumina In ethanol for 1h; Claisen-Schmidt Condensation; Reflux;
53-43-0

dehydroepiandrosterone

529-20-4

2-methylphenyl aldehyde

1428382-57-3

(E)-16-(2-methylphenyl)methylidene-trans-dehydroandrosterone

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 1h;98%
53-43-0

dehydroepiandrosterone

1576-35-8

toluene-4-sulfonic acid hydrazide

34988-34-6

dehydroepiandrosterone-17-p-toluenesulfonyl hydrazone

Conditions
ConditionsYield
With toluene-4-sulfonic acid In tetrahydrofuran Inert atmosphere; Reflux;98%
With toluene-4-sulfonic acid In tetrahydrofuran Reflux; Inert atmosphere;98%
With toluene-4-sulfonic acid In tetrahydrofuran for 3h; Inert atmosphere;98%
With sulfuric acid In methanol for 5h; Reflux;91.6%
With sulfuric acid In methanol at 15℃; for 2h; Concentration; Reflux;81.4%
53-43-0

dehydroepiandrosterone

1325724-92-2

1-(3,4-dichlorophenyl)-1H-1,2,3-triazole-4-carbaldehyde

(E)-16-((1-(3,4-dichlorophenyl)-1H-1,2,3-triazol-4-yl)methylene)-3-hydroxy-10,13-dimethyl-1,3,4,7,8,9,10,11,12,13,15,16-dodecahydro-2H-cyclopenta[a]phenanthren-17(14H)-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 1h; Reflux;98%
53-43-0

dehydroepiandrosterone

1-(2-bromophenyl)-4,5-dihydro-1H-1,2,3-triazole-4-carbaldehyde

(E)-16-((1-(2-bromophenyl)-1H-1,2,3-triazol-4-yl)methylene)-3-hydroxy-10,13-dimethyl-1,3,4,7,8,9,10,11,12,13,15,16-dodecahydro-2H-cyclopenta[a]phenanthren-17(14H)-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 1h; Reflux;98%
53-43-0

dehydroepiandrosterone

C9H6BrN3O

(E)-16-((1-(3-bromophenyl)-1H-1,2,3-triazol-4-yl)methylene)-3-hydroxy-10,13-dimethyl-1,3,4,7,8,9,10,11,12,13,15,16-dodecahydro-2H-cyclopenta[a]phenanthren-17(14H)-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 1h; Reflux;98%
53-43-0

dehydroepiandrosterone

1-(2-fluorophenyl)-4,5-dihydro-1H-1,2,3-triazole-4-carbaldehyde

(E)-16-((1-(2-fluorophenyl)-1H-1,2,3-triazol-4-yl)methylene)-3-hydroxy-10,13-dimethyl-1,3,4,7,8,9,10,11,12,13,15,16-dodecahydro-2H-cyclopenta[a]phenanthren-17(14H)-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 1h; Reflux;98%
53-43-0

dehydroepiandrosterone

1-(3-fluorophenyl)-4,5-dihydro-1H-1,2,3-triazole-4-carbaldehyde

(E)-16-((1-(3-fluorophenyl)-1H-1,2,3-triazol-4-yl)methylene)-3-hydroxy-10,13-dimethyl-1,3,4,7,8,9,10,11,12,13,15,16-dodecahydro-2H-cyclopenta[a]phenanthren-17(14H)-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 1h; Reflux;98%
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Chemistry

Molecule structure of Dehydroepiandrosterone (CAS NO.53-43-0):

IUPAC Name: (3S,8R,9S,10R,13S,14S)-3-Hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one 
Molecular Weight: 288.42442 g/mol
Molecular Formula: C19H28O2 
Density: 1.12 g/cm3
Melting Point: 149-151 °C(lit.)
Boiling Point: 426.7 °C at 760 mmHg 
Flash Point: 182.1 °C
Index of Refraction: 1.56
Molar Refractivity: 83.11 cm3
Molar Volume: 256.9 cm3
Polarizability: 32.94×10-24 cm3
Surface Tension: 44.4 dyne/cm  
Enthalpy of Vaporization: 78.7 kJ/mol
Vapour Pressure: 4.54E-09 mmHg at 25 °C
XLogP3: 3.2
H-Bond Donor: 1
H-Bond Acceptor: 2
Tautomer Count: 2
Exact Mass: 288.20893
MonoIsotopic Mass: 288.20893
Topological Polar Surface Area: 37.3
Heavy Atom Count: 21
Complexity: 508
Canonical SMILES: CC12CCC3C(C1CCC2=O)CC=C4C3(CCC(C4)O)C
Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC=C4[C@@]3(CC[C@@H](C4)O)C
InChI: InChI=1S/C19H28O2/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/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1
InChIKey: FMGSKLZLMKYGDP-USOAJAOKSA-NEINECS: 200-175-5
Product Categories: Pharmaceutical Intermediates; Steroids; 17-Ketosteroids; Biochemistry; Hydroxyketosteroids; Nutritional Supplements

Uses

 Dehydroepiandrosterone (53-43-0) is used as the main raw material of steroid hormone drugs and contraceptives.

Production

 Dehydroepiandrosterone is produced from cholesterol through two cytochrome P450 enzymes. Cholesterol is converted to pregnenolone by the enzyme P450 scc (side chain cleavage); then another enzyme, CYP17A1, converts pregnenolone to 17α-Hydroxypregnenolone and then to DHEA.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 10mg/kg/2W-I (10mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) Annals of Internal Medicine. Vol. 129, Pg. 588, 1998.
mouse LD50 oral > 10gm/kg (10000mg/kg)   British UK Patent Application. Vol. #2208473,
mouse LD50 subcutaneous 900mg/kg (900mg/kg)   British UK Patent Application. Vol. #2208473,
rat LD50 oral > 10gm/kg (10000mg/kg)   British UK Patent Application. Vol. #2208473,
rat LD50 subcutaneous 1gm/kg (1000mg/kg)   British UK Patent Application. Vol. #2208473,

Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-24/25 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S24/25:Avoid contact with skin and eyes.
WGK Germany: 2
RTECS: BV8396000

Specification

 Dehydroepiandrosterone (CAS NO.53-43-0) is also named as (3-beta)-3-Hydroxyandrost-5-en-17-one ; 17-Chetovis ; 17-Hormoforin ; 3-beta-Hydroxy-5-androsten-17-one ; 3beta-Hydroxyandrost-5-en-17-one ; 4-08-00-00994 (Beilstein Handbook Reference) ; 5,6-Dehydroisoandrosterone ; 5,6-Dehydroisoandrostorone ; 5,6-Didehydroisoandrosterone ; 5-Dehydroepiandrosterone ; Andrestenol ; Androstenolone ; BRN 2058110 ; CCRIS 3277 ; Caswell No. 051F ; DHEA ;
Diandron ; Diandrone ; EPA Pesticide Chemical Code 126510 ; Epiandrosterone, 5-dehydro- ; GL 701 ; Gynodian ; NSC 9896 ; Prasterona ; Prasterona [INN-Spanish] ; Prasterone ; Prasteronum ; Prasteronum [INN-Latin] ; Prestara ; Psicosterone ; Siscelar plus ; UNII-459AG36T1B ; trans-Dehydroandrosterone . Dehydroepiandrosterone (CAS NO.53-43-0) is white fine crystalline powder. It is soluble in benzene, ethanol, ethyl ether, insoluble in chloroform, petroleum ether
is toxic. It is flammable. It will produce stimulate smoke when buring. So the storage environment should be ventilate, low-
temperature and dry.

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