Hydroxyprogesterone acetate Chemical Properties

Melting point:

249-250°C

Boiling point:

421.94°C (rough estimate)

Density 

1.0415 (rough estimate)

refractive index 

1.4433 (estimate)

storage temp. 

Sealed in dry,2-8°C

solubility 

Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Sparingly)

Water Solubility 

1.01mg/L at 20℃

λmax

241nm(EtOH)(lit.)

BRN 

2227870

InChI

InChI=1S/C23H32O4/c1-14(24)23(27-15(2)25)12-9-20-18-6-5-16-13-17(26)7-10-21(16,3)19(18)8-11-22(20,23)4/h13,18-20H,5-12H2,1-4H3/t18-,19+,20+,21+,22+,23+/m1/s1

InChIKey

VTHUYJIXSMGYOQ-KOORYGTMSA-N

SMILES

C1(=O)C=C2[C@](C)(CC1)[C@]1([H])[C@]([H])([C@@]3([H])[C@@](CC1)(C)[C@@](OC(C)=O)(C(=O)C)CC3)CC2

CAS DataBase Reference

302-23-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

40-48

Safety Statements 

22-24/25-45

RIDADR 

UN 2811 6.1/PG 2

WGK Germany 

3

RTECS 

TU5074000

HS Code 

29372390

Hydroxyprogesterone acetate Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

Progesterone Acetate (Megestrol Acetate EP Impurity K) is an impurity in steroid drug Megestrol acetate (M208050).

Uses

An impurity in steroid drug Megestrol acetate (M208050).

Synthesis

The general procedure for the synthesis of the target compound (CAS: 4134-58-1) using the compound (CAS: 83984-86-5) as starting material was as follows: the diester (51 g, melting point 192-196°C) was dissolved in a solvent mixture of 1.4 liters of technical grade xylene and 510 ml of cyclohexanone. Water was removed from the system by distillation (250 ml of distillate was collected). Subsequently, aluminum isopropoxide (51 g) dissolved in 210 ml of xylene was added dropwise to the reaction system over a period of 5 minutes under slow distillation conditions, and distillation was continued for 45 minutes (another 210 ml of distillate was collected). Upon completion of the reaction, the mixture was rapidly cooled, the reaction was quenched by the addition of an ice-water mixture, and the remaining solvent was removed by steam distillation. The resulting solid product was collected by filtration and dried. The crude product was extracted using hot acetone and subsequently recrystallized by acetone to give 40.7 g (86% yield) of 17α-acetoxy-progesterone with a melting point of 240-243 °C. The melting point of the further purified sample was raised to 243-247 °C. *The 2% yield of the raw material is equivalent to 78.95%.

References

[1] Patent: EP1359154, 2003, A1. Location in patent: Page/Page column 16; 28; 30; 32
[2] Journal of the American Chemical Society, 1956, vol. 78, p. 820,823

Hydroxyprogesterone acetate(302-23-8)Related Product Information

• Ammonium acetate
• 4-(Diethylamino)salicylaldehyde
• Benzyl acetate
• Sodium acetate
• DL-α-Tocopherol
• Isopropyl acetate
• CHLOROPHOSPHONAZO III
• Cellulose acetate
• Ethyl acetate
• Diphenolic acid
• 5-Chlorovaleric acid
• Pralmorelin
• Butyl acetate
• Vinyl acetate
• Medroxyprogesterone Acetate
• Megestrol acetate
• Cyproterone acetate
• Magnesium acetate