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Name	Dehydroepiandrosterone	EINECS	200-175-5
CAS No.	53-43-0	Density	1.12 g/cm³
PSA	37.30000	LogP	3.87920
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	N/A	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];	Article Data	142

Dehydroepiandrosterone 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%

: 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

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.

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