Basic information
- Name:
Dehydroepiandrosterone
- CAS No.:
53-43-0
- Molecular Structure:
- 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
- Appearance:
- white fine crystalline powder
- Hazard Symbols:
Xi- Risk Codes:
- 36/37/38
- Safety Description:
- 26-36-24/25 Details
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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: 
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
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.