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979-02-2

Basic Information
CAS No.: 979-02-2
Name: 16-Dehydropregnenolone acetate
Article Data: 94
Molecular Structure:
Molecular Structure of 979-02-2 (16-Dehydropregnenolone acetate)
Formula: C23H32O3
Molecular Weight: 356.505
Synonyms: 20-oxopregna-5,16-dien-3-β-yl acetate;16-Denyprasterone Acetate;16-Denyprasterone Acetate(16-DPA);16-Dehydropregnenolone Acetate(16-DPA);16 Dehydropregneninolone, Acetate;Pregna-5,16-dien-20-one, 3- (acetyloxy)-, (3.beta.)-;20-Oxopregna-5, 16-dien-3.beta.-yl acetate;Dehydropregnenolone acetate;Pregna-5,16-dien-20-one, 3-beta-hydroxy-, acetate;Pregna-5,16-dien-20-one, 3beta-hydroxy-, acetate (8CI);4-08-00-01125 (Beilstein Handbook Reference);16,17-Didehydropregnenolone acetate;3.beta.-Acetoxypregna-5,16-dien-20-one;20-Oxopregna-5,16-dien-3-beta-yl acetate;(3-beta)-3-(Acetyloxy)pregna-5,16-dien-20-one;Pregna-5,16-dien-20-one, 3.beta.-hydroxy-, acetate;
EINECS: 213-558-7
Density: 1.11g/cm3
Melting Point: 170-178 °C
Boiling Point: 464.4 °C at 760mmHg
Flash Point: 200.1 °C
Appearance: White to almost white crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37/39
PSA: 43.37000
LogP: 5.00620
Synthetic route
23549-24-8, 23549-26-0, 2174-13-2

3β-acetoxy-20-hydroxyiminopregna-5,16-diene

979-02-2

16-dehydropregnenolone acetate

Conditions
ConditionsYield
With Dess-Martin periodane In dichloromethane; water for 0.333333h;95%
86284-34-6

(3β)-21-bromo-20-oxopregna-5,16-dien-3-yl acetate

979-02-2

16-dehydropregnenolone acetate

Conditions
ConditionsYield
With aluminum oxide; zirconium(IV) chloride; benzaldehyde microwave irradiation;88%
115375-60-5

3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate

109-92-2

ethyl vinyl ether

A

16934-48-8

(Z/E)-3β-Acetoxypregna-5,17(20)-dien-21-al

B

979-02-2

16-dehydropregnenolone acetate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); triethylamine In dimethyl sulfoxide at 60℃; for 4h;A 8%
B 82%
136321-38-5

Tributyl-[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-stannane

75-36-5

acetyl chloride

A

1236-14-2

3β-acetoxyandrost-5,16-diene

B

979-02-2

16-dehydropregnenolone acetate

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; bis(benzonitrile)palladium(II) dichloride at 80℃; for 8h;A 80%
B 30%
3517-38-2

3β,17α-diacetoxypregn-5-en-20-one

979-02-2

16-dehydropregnenolone acetate

Conditions
ConditionsYield
80%
64-19-7

acetic acid

126-17-0

solasodine

979-02-2

16-dehydropregnenolone acetate

Conditions
ConditionsYield
Stage #1: solasodine With pyridine; ammonium chloride at 125 - 135℃; for 8 - 9h;
Stage #2: acetic acid With chromium(VI) oxide In water; 1,2-dichloro-ethane at 0 - 20℃; for 1h; Product distribution / selectivity;
65%
2309-38-8

pseudodiosgenin diacetate

979-02-2

16-dehydropregnenolone acetate

Conditions
ConditionsYield
With chromium(VI) oxide; acetic acid41%
Stage #1: pseudodiosgenin diacetate With potassium permanganate; sodium perchlorate In dichloromethane; water for 0.05h;
Stage #2: N-benzyl-N,N,N-triethylammonium chloride In dichloromethane; water at 20℃; for 6h;
Stage #3: With acetic acid for 3h; Product distribution / selectivity; Heating / reflux;
32%
Stage #1: pseudodiosgenin diacetate With potassium permanganate; sodium iodate In dichloromethane; water for 0.05h;
Stage #2: N-benzyl-N,N,N-triethylammonium chloride In dichloromethane; water at 20℃; for 10h;
Stage #3: With acetic acid for 3h; Product distribution / selectivity; Heating / reflux;
32%
58026-06-5

3',4',6'-tri-O-acetyl-1',2',O-(16-dehydropregnenolone-3-yloxyethylidene)-α-D-glucopyranose

A

1162-53-4

16-dehydropregnenolone

B

979-02-2

16-dehydropregnenolone acetate

C

93238-36-9

di-16-dehydropregnenolone-2-yl ether

D

13407-28-8

3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-16-dehydropregnanolone

E

93269-28-4

3-O-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-16-dehydropregnenolone

Conditions
ConditionsYield
With mercury dibromide In nitromethane at 90℃; for 1h; Product distribution; other molar ratio, other time;A 2%
B 8%
C 14%
D 36.3%
E 4%
58026-06-5

3',4',6'-tri-O-acetyl-1',2',O-(16-dehydropregnenolone-3-yloxyethylidene)-α-D-glucopyranose

A

979-02-2

16-dehydropregnenolone acetate

B

93238-36-9

di-16-dehydropregnenolone-2-yl ether

C

13407-28-8

3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-16-dehydropregnanolone

D

93269-28-4

3-O-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-16-dehydropregnenolone

Conditions
ConditionsYield
With mercury dibromide In nitromethane at 90℃; for 1h; Further byproducts given;A 8%
B 14%
C 36.3%
D 4%
30040-85-8

(25R)-22,26-epiminocholesta-5,22(N)-diene-3β,16β-diol diacetate

A

979-02-2

16-dehydropregnenolone acetate

B

(20S)-3β,16β-diacetoxy-20-(5-methyl-2-pyridyl)pregn-5-ene

C

(25R)-3β,16β-diacetoxy-22,26-epiminocholest-5,22(N)-dien-23-one

Conditions
ConditionsYield
With manganese(IV) oxide In chloroform for 48h; Ambient temperature;A 5%
B 6%
C 16%
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  • 16-Dehydropregnenolone acetate CAS: 979-02-2

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Chemistry

Molecular Structure of 16-Dehydropregnenolone acetate (CAS NO.979-02-2):

IUPAC Name: [(3S,8R,9S,10R,13S,14S)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate 
Empirical Formula: C23H32O3
Molecular Weight: 356.4984
H bond acceptors: 3
H bond donors: 0
Freely Rotating Bonds: 3
Polar Surface Area: 43.37 Å2
Index of Refraction: 1.546
Molar Refractivity: 101.63 cm3
Molar Volume: 320.5 cm3
Surface Tension: 42 dyne/cm
Density: 1.11 g/cm3
Flash Point: 200.1 °C
Enthalpy of Vaporization: 72.58 kJ/mol
Boiling Point: 464.4 °C at 760 mmHg
Vapour Pressure: 8.38E-09 mmHg at 25°C
Melting point: 170-178°C
InChI
InChI=1/C23H32O3/c1-14(24)19-7-8-20-18-6-5-16-13-17(26-15(2)25)9-11-22(16,3)21(18)10-12-23(19,20)4/h5,7,17-18,20-21H,6,8-13H2,1-4H3/t17-,18-,20-,21-,22-,23+/m0/s1
Smiles
O=C(C)C1=CC[C@@H]2[C@@]1(CC[C@@H]1[C@@]3(CC[C@H](OC(=O)C)CC3=CC[C@@H]21)C)C
EINECS: 213-558-7
Product Categories: Steroids

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 8gm/kg (8000mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 18(2), Pg. 32, 1974.
mouse LD50 oral > 8gm/kg (8000mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 18(2), Pg. 32, 1974.

Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S37/39:Wear suitable gloves and eye/face protection.
RTECS: TU4156200

Specification

  16-Dehydropregnenolone acetate , with CAS number of 979-02-2, can be called Pregna-5,16-dien-20-one, 3-beta-hydroxy-, acetate ; Dehydropregnenolone acetate ; 3beta-Acetoxypregna-5,16-dien-20-one ; 20-Oxopregna-5,16-dien-3beta-yl acetate ; 16-Dehydropregnenolone acetate ; 16,17-Didehydropregnenolone acetate ; (3-beta)-3-(Acetyloxy)pregna-5,16-dien-20-one .