Dehydroepiandrosterone supplier

Name
Dehydroepiandrosterone
EINECS 200-175-5
CAS No. 53-43-0
Article Data142
CAS DataBase
Density 1.12 g/cm³
Solubility 21.8mg/L(23.5 oC)
Melting Point 149-151 °C(lit.)
Formula C₁₉H₂₈O₂
Boiling Point 426.7 °C at 760 mmHg
Molecular Weight 288.43
Flash Point 182.1 °C
Transport Information
Appearance white fine crystalline powder
Safety 26-36-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
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];
PSA 37.30000
LogP 3.87920

Synthetic route

: 853-23-6
prasterone acetate

: 53-43-0
dehydroepiandrosterone

Conditions

Conditions	Yield
With sodium hydroxide In methanol	98.54%
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

Conditions	Yield
With Me3SiN=CMe(1+)*BF4(1-); water In acetonitrile	96%

: 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

Conditions	Yield
With Me3SiN=CMe(1+)*BF4(1-); water In acetonitrile	96%

: 327622-68-4
(17Ξ)-spiro[androst-5-en-17,2'-[1,3]oxathiolan]-3β-ol

: 53-43-0
dehydroepiandrosterone

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

...Expand

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

: 53-43-0
dehydroepiandrosterone

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: C28H47NO2

: 53-43-0
dehydroepiandrosterone

Conditions

Conditions	Yield
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

Conditions	Yield
With pyridine In tetrahydrofuran	A 45% B 8% C 20%

...Expand

: 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

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

...Expand

: 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

Conditions	Yield
Multistep reaction;	A 22% B 35%

: 57-88-5
cholesterol

A: 53-43-0
dehydroepiandrosterone

B: 63-05-8
Androstenedione

Conditions

Conditions	Yield
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

Conditions	Yield
Multistep reaction;	A 21% B 19% C 25%

...Expand

: 145-13-1
Pregnenolone

A: 53-43-0
dehydroepiandrosterone

B: 34069-59-5
17α-Hydroperoxy-5-pregnen-3β-ol-20-on

Conditions

Conditions	Yield
With 18-crown-6 ether In tetrahydrofuran; benzene at 18℃; under 760 Torr; for 24h;	A 23% B 9%

: 145-13-1
Pregnenolone

A: 53-43-0
dehydroepiandrosterone

B: 521-17-5, 1963-03-7, 4593-57-1, 4593-58-2, 14504-94-0, 16895-59-3, 47122-33-8, 64162-67-0, 75767-22-5, 139973-51-6, 151284-19-4
5-androstenediol

C: 3β,15β-dihydroxy-5-androsten-17-one

Conditions

Conditions	Yield
With Gelasinospora retispora GRK002 In methanol; water at 34℃; for 336h; pH=5; Microbiological reaction;	A 23% B 18% C 11%

...Expand

: 145-13-1
Pregnenolone

A: 53-43-0
dehydroepiandrosterone

B: 387-79-1
17-Hydroxypregnenolone

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With ethanol; nickel Hydrogenation;

: 83205-52-1, 2080-86-6
3β-benzoyloxy-androst-5-en-17-one

: 53-43-0
dehydroepiandrosterone

Conditions

Conditions	Yield
With potassium hydroxide
With potassium hydroxide

: 4350-66-7
17β-Aminoandrost-5-en-3β-ol

: 53-43-0
dehydroepiandrosterone

Conditions

Conditions	Yield
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

Conditions	Yield
unter vermindertem Druck;
at 110 - 120℃;

: 60446-55-1
3β-acetoxy-20-methyl-pregnadiene-(5,17(20))

: 53-43-0
dehydroepiandrosterone

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 120h; Ambient temperature;	100%
With impramine	99%
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

Dehydroepiandrosterone Chemical Properties

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

Dehydroepiandrosterone Uses

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

Dehydroepiandrosterone 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.

Dehydroepiandrosterone 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,

Dehydroepiandrosterone Safety Profile

Hazard Codes: Irritant Xi
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

Dehydroepiandrosterone 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.

Product Name

Dehydroepiandrosterone

Synthetic route

Dehydroepiandrosterone Chemical Properties

Dehydroepiandrosterone Uses

Dehydroepiandrosterone Production

Dehydroepiandrosterone Toxicity Data With Reference

Dehydroepiandrosterone Safety Profile

Dehydroepiandrosterone Specification

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