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Basic Information
CAS No.: 53-43-0
Name: Dehydroepiandrosterone
Article Data: 142
Molecular Structure:
Molecular Structure of 53-43-0 (Dehydroepiandrosterone)
Formula: C19H28O2
Molecular Weight: 288.43
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
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
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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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