Product Name

  • Name

    Dehydroandrosterone

  • EINECS
  • CAS No. 2283-82-1
  • Article Data35
  • CAS DataBase
  • Density 1.12 g/cm3
  • Solubility
  • Melting Point 148 °C
  • Formula C19H28O2
  • Boiling Point 426.7 °C at 760 mmHg
  • Molecular Weight 288.43
  • Flash Point 182.1 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 2283-82-1 (Dehydroandrosterone)
  • Hazard Symbols
  • Synonyms Androst-5-en-17-one,3a-hydroxy- (8CI);3a-Hydroxy-5-androsten-17-one;Androst-5-en-3a-ol-17-one;Dehydroandrosterone;Isoandrostenolone;D5-Androstene-3a-ol-17-one;
  • PSA 37.30000
  • LogP 3.87920

Synthetic route

(3R,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 acetate
5223-99-4

(3R,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 acetate

3α-hydroxy-androst-5-en-17-one
2283-82-1

3α-hydroxy-androst-5-en-17-one

Conditions
ConditionsYield
With methanol; sodium hydroxide at 40℃; for 4h; Inert atmosphere;95.8%
With potassium hydroxide In methanol for 1h; Heating;1.9 g
17,17-ethylenedioxy-androst-5-ene-3α-ol
14456-21-4

17,17-ethylenedioxy-androst-5-ene-3α-ol

3α-hydroxy-androst-5-en-17-one
2283-82-1

3α-hydroxy-androst-5-en-17-one

Conditions
ConditionsYield
With hydrogenchloride80%
With hydrogenchloride In ethanol; water for 5h; Reflux;
dehydroepiandrosterone p-nitrobenzoate
1383292-25-8

dehydroepiandrosterone p-nitrobenzoate

3α-hydroxy-androst-5-en-17-one
2283-82-1

3α-hydroxy-androst-5-en-17-one

Conditions
ConditionsYield
With potassium hydroxide In methanol; water for 1h; Sonication;72%
With NaOH In tetrahydrofuran; methanol; water
5-androstenedione
571-36-8

5-androstenedione

A

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

B

3α-hydroxy-androst-5-en-17-one
2283-82-1

3α-hydroxy-androst-5-en-17-one

Conditions
ConditionsYield
With ethanol; nickel Hydrogenation;
3β-tosyloxyandrost-5-ene-17-one
2719-96-2

3β-tosyloxyandrost-5-ene-17-one

3α-hydroxy-androst-5-en-17-one
2283-82-1

3α-hydroxy-androst-5-en-17-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 3.2 g / various solvent(s) / 4 h / 160 °C
2: 1.9 g / aq. KOH / methanol / 1 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 3.2 g / tetra-n-butylammonium acetate / various solvent(s) / 4 h / 160 °C
2: 1.9 g / aq. KOH / methanol / 1 h / Heating
View Scheme
3β-acetoxy-5α,6α-epoxy-androst-17-one, ethylene ketal
115350-45-3

3β-acetoxy-5α,6α-epoxy-androst-17-one, ethylene ketal

3α-hydroxy-androst-5-en-17-one
2283-82-1

3α-hydroxy-androst-5-en-17-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: lithium aluminium tetrahydride
2: pyridine
3: N,N-dimethyl-aniline
4: potassium hydroxide
5: hydrogenchloride
View Scheme
Multi-step reaction with 5 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 35 °C / Reflux
2: pyridine / dichloromethane / 16 h / 10 - 20 °C / Cooling with ice
3: N,N-dimethyl-aniline / chloroform / 5 h / Reflux
4: potassium hydroxide; water / methanol / 1 h / Reflux
5: hydrogenchloride / ethanol; water / 5 h / Reflux
View Scheme
17,17-ethylenedioxy-androstane-3β,5α-diol

17,17-ethylenedioxy-androstane-3β,5α-diol

3α-hydroxy-androst-5-en-17-one
2283-82-1

3α-hydroxy-androst-5-en-17-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine
2: N,N-dimethyl-aniline
3: potassium hydroxide
4: hydrogenchloride
View Scheme
Multi-step reaction with 4 steps
1: pyridine / dichloromethane / 16 h / 10 - 20 °C / Cooling with ice
2: N,N-dimethyl-aniline / chloroform / 5 h / Reflux
3: potassium hydroxide; water / methanol / 1 h / Reflux
4: hydrogenchloride / ethanol; water / 5 h / Reflux
View Scheme
17,17-ethylenedioxy-3β-methanesulfonyloxy-androstane-5α-ol
15577-68-1

17,17-ethylenedioxy-3β-methanesulfonyloxy-androstane-5α-ol

3α-hydroxy-androst-5-en-17-one
2283-82-1

3α-hydroxy-androst-5-en-17-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N,N-dimethyl-aniline
2: potassium hydroxide
3: hydrogenchloride
View Scheme
Multi-step reaction with 3 steps
1: N,N-dimethyl-aniline / chloroform / 5 h / Reflux
2: potassium hydroxide; water / methanol / 1 h / Reflux
3: hydrogenchloride / ethanol; water / 5 h / Reflux
View Scheme
5-androsten-3α-ol-17-one acetate 17-ethylene ketal
14456-20-3

5-androsten-3α-ol-17-one acetate 17-ethylene ketal

3α-hydroxy-androst-5-en-17-one
2283-82-1

3α-hydroxy-androst-5-en-17-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium hydroxide
2: hydrogenchloride
View Scheme
Multi-step reaction with 2 steps
1: potassium hydroxide; water / methanol / 1 h / Reflux
2: hydrogenchloride / ethanol; water / 5 h / Reflux
View Scheme
prasterone acetate

prasterone acetate

3α-hydroxy-androst-5-en-17-one
2283-82-1

3α-hydroxy-androst-5-en-17-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: p-toluenesulfonic acid monohydrate
2: 3-chloro-benzenecarboperoxoic acid
3: lithium aluminium tetrahydride
4: pyridine
5: N,N-dimethyl-aniline
6: potassium hydroxide
7: hydrogenchloride
View Scheme
Multi-step reaction with 7 steps
1: orthoformic acid triethyl ester / toluene-4-sulfonic acid / 3 h / Inert atmosphere; Reflux
2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / -5 - 20 °C
3: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 35 °C / Reflux
4: pyridine / dichloromethane / 16 h / 10 - 20 °C / Cooling with ice
5: N,N-dimethyl-aniline / chloroform / 5 h / Reflux
6: potassium hydroxide; water / methanol / 1 h / Reflux
7: hydrogenchloride / ethanol; water / 5 h / Reflux
View Scheme

3α-hydroxy-androst-5-en-17-one

3α-hydroxy-androst-5-en-17-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 3-chloro-benzenecarboperoxoic acid
2: lithium aluminium tetrahydride
3: pyridine
4: N,N-dimethyl-aniline
5: potassium hydroxide
6: hydrogenchloride
View Scheme
Multi-step reaction with 6 steps
1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / -5 - 20 °C
2: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 35 °C / Reflux
3: pyridine / dichloromethane / 16 h / 10 - 20 °C / Cooling with ice
4: N,N-dimethyl-aniline / chloroform / 5 h / Reflux
5: potassium hydroxide; water / methanol / 1 h / Reflux
6: hydrogenchloride / ethanol; water / 5 h / Reflux
View Scheme
Androstenedione
63-05-8

Androstenedione

3α-hydroxy-androst-5-en-17-one
2283-82-1

3α-hydroxy-androst-5-en-17-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium tert-butylate / tert-butyl alcohol / 1 h / 30 - 35 °C / Inert atmosphere
1.3: 65 h / 45 °C / pH 6.5 / Enzymatic reaction
2.1: 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
3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 5 - 20 °C / Inert atmosphere
4.1: potassium hydroxide / water; methanol / 1 h / Sonication
View Scheme
Multi-step reaction with 4 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
3: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 5 - 20 °C / Inert atmosphere
4: potassium hydroxide / water; methanol / 1 h / Sonication
View Scheme
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

3α-hydroxy-androst-5-en-17-one
2283-82-1

3α-hydroxy-androst-5-en-17-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 5 - 20 °C / Inert atmosphere
2: potassium hydroxide / water; methanol / 1 h / Sonication
View Scheme
5-androstenedione
571-36-8

5-androstenedione

3α-hydroxy-androst-5-en-17-one
2283-82-1

3α-hydroxy-androst-5-en-17-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 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
2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 5 - 20 °C / Inert atmosphere
3: potassium hydroxide / water; methanol / 1 h / Sonication
View Scheme

Dehydroandrosterone Specification

The Dehydroandrosterone with the cas number 2283-82-1 is also called Androst-5-en-17-one, 3-hydroxy-, (3alpha)-.The IUPAC name is (3R,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. Its molecular formula is C19H28O2. This chemical is a kind of organics. It should be stored in dry and cool environment.

The properties of the chemical are: (1)ACD/LogP: 3.42; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.42; (4)ACD/LogD (pH 7.4): 3.42; (5)ACD/BCF (pH 5.5): 234.6; (6)ACD/BCF (pH 7.4): 234.6; (7)ACD/KOC (pH 5.5): 1730.96; (8)ACD/KOC (pH 7.4): 1730.96; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.56; (14)Molar Refractivity: 83.11 cm3; (15)Molar Volume: 256.9 cm3; (16)Polarizability: 32.94×10-24cm3; (17)Surface Tension: 44.4 dyne/cm; (18)Enthalpy of Vaporization: 78.7 kJ/mol; (19)Vapour Pressure: 4.54×10-9 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C3[C@]2(CC[C@@H]1[C@@]4(C(=C/C[C@H]1[C@@H]2CC3)\C[C@H](O)CC4)C)C
(2)InChI: InChI=1/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+/m1/s1
(3)InChIKey: FMGSKLZLMKYGDP-HKQXQEGQBW

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