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| CAS No.: | 595-33-5 |
|---|---|
| Name: | Megestrol acetate |
| Article Data: | 30 |
| Molecular Structure: | |
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|
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| Formula: | C24H32O4 |
| Molecular Weight: | 384.516 |
| Synonyms: | Megace ES;Pregna-4,6-diene-3,20-dione, 17-(acetyloxy)-6-methyl-;Ovarid;Megace;Ovaban (Veterinary);Megeron;6-Methyl-delta4,6-pregnadien-17alpha-ol-3,20-dione acetate;6-Methyl-6-dehydro-17.alpha.-acetoxyprogesterone;Megace (TN);SC 10363;Megestryl acetate;Pregna-4,6-diene-3, 20-dione, 17-hydroxy-6-methyl-, acetate;Pallace;Ovaban;S4;6-Methyl-17-alpha-hydroxy-delta(sup 6)-progesterone acetate;SC-10363;SC10363;Niagestin;Progesterone, 6-dehydro-17-hydroxy-6-methyl-, acetate;6-Methyl-delta(sup 4,6)-pregnadien-17-alpha-ol-3,20-dione acetate;Megestrol acetate [USAN];17alpha-Acetoxy-6-dehydro-6-methylprogesterone;Megestrol acetate (USAN);Megestat;6-Dehydro-6-methyl-17.alpha.-acetoxyprogesterone;17-Hydroxy-6-methylpregna-4,6-diene-3,20-dione acetate;Megestrol acetole [Progestins];6-MethleneProgesterone Acetate;Pregna-4,6-diene-3, 20-dione, 17- (acetyloxy)-6-methyl-;BDH 1298; |
| EINECS: | 209-864-5 |
| Density: | 1.15 g/cm3 |
| Melting Point: | 214 °C |
| Boiling Point: | 507.1 °C at 760 mmHg |
| Flash Point: | 218.5 °C |
| Appearance: | Crystalline Solid |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 40-48 |
| Safety: | 22-24/25 |
| PSA: | 60.44000 |
| LogP: | 4.57530 |
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| Conditions | Yield |
|---|---|
| Stage #1: methyl bromide; C27H38O7 With magnesium In tetrahydrofuran at 30 - 55℃; Inert atmosphere; Stage #2: With hydrogenchloride In water at 60 - 65℃; | 69.8% |
- 4382-76-7
methoxymethyl acetate
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hydroxyprogesterone acetate
- 595-33-5
Megestrol acetate
| Conditions | Yield |
|---|---|
| With sodium acetate; trichlorophosphate In chloroform at 70℃; for 0.166667h; | 51% |
| With sodium acetate; trichlorophosphate In chloroform |
| Conditions | Yield |
|---|---|
| With chloranil | |
| With 2-methyl-propan-1-ol; chloranil Heating; | |
| With chloranil | |
| Multi-step reaction with 2 steps 1: TsOH / dioxane 2: (tBuO)2CrO2, Ac2O / CCl4 View Scheme |
- 71-58-9
Medroxyprogesterone acetate
- 118-75-2
chloranil
- 64-19-7
acetic acid
- 141-78-6
ethyl acetate
- 595-33-5
Megestrol acetate
- 71-58-9
Medroxyprogesterone acetate
- 118-75-2
chloranil
- 75-65-0
tert-butyl alcohol
- 595-33-5
Megestrol acetate
| Conditions | Yield |
|---|---|
| With acetic anhydride In tetrachloromethane |
| Conditions | Yield |
|---|---|
| With aluminum tri-tert-butoxide; p-benzoquinone |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 8 steps 1: benzene; toluene-4-sulfonic acid 2: peroxybenzoic acid; chloroform 3: benzene; diethyl ether 4: aqueous methanol.H2SO4 5: CrO3; pyridine 6: aqueous HCl 7: acetic acid; toluene-4-sulfonic acid 8: tetrachloro-<1,4>benzoquinone View Scheme |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: acetic acid; toluene-4-sulfonic acid 2: tetrachloro-<1,4>benzoquinone View Scheme |
- 113665-92-2
3β,5,17-trihydroxy-6β-methyl-5α-pregnan-20-one
- 595-33-5
Megestrol acetate
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1: CrO3; pyridine 2: aqueous HCl 3: acetic acid; toluene-4-sulfonic acid 4: tetrachloro-<1,4>benzoquinone View Scheme |
- 59535-09-0Polyethylene glycol, ether with 4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol (2:1)
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Chemistry
Name:17-Acetyloxy-6-methylpregna-4,6-diene-3,20-dione
Other names:Megestrol acetate;6-diene-3,20-dione;17-hydroxy-6-methyl-pregna-acetate;17- (acetyloxy)-6-methylpregna-4 ,6-dien-3,20-dione;17-acetoxy-6-methylpregna-4, 6-dien-3;20-dione;megestrol acetate acetate; 17α-acetoxy-6-methyl-pregn-4 ,6-diene-;6-methyl-pregn-4 ,6-dien-17 alpha-ol ,20 - dione-17-acetate
17α-hydroxy-6-methyl-;16-4,6-diene; 20-dione-17-acetate
Molecular formula : C24H32O4
MW : 384.52
refractive index: 11°C (C=2, CHCl3)
Melting point:214-216 °C
ACD/LogP(pH 5.5): 3.82
ACD/LogP(pH 5.5): 3.82
ACDXLogP: 3.90
nature : a white or slightly yellow crystalline powder in methanol, tasteless, odorless.Soluble acetone, ethanol-soluble, ether, do not dissolve in water.
Uses
Production
available 16-17α-dione by the open-loop hydrogen bromide and nickel Catalytic Reduction of bromine, in the production of 17 alpha-hydroxy progesterone, and then acetylated and acid hydrolysis of the production of 17 alpha-acetoxy progesterone, and then to the original three formic acid and ethyl ether of Vilsmeier reacted 3-ethoxy-6-formyl-17α- acetoxy ,16 ,5-diene-20-one, and the final KBH4, acid hydrolysis, dehydration and transposition of the goods obtained.
Toxicity Data With Reference
| 1. | dns-mus-scu 200 mg/kg | JOENAK Journal of Endocrinology. 60 (1974),167. | ||
| 2. | dni-mus-scu 200 mg/kg | JOENAK Journal of Endocrinology. 60 (1974),167. | ||
| 3. | ivn-mus LD50:56 mg/kg | CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#00931 . |
Consensus Reports
Safety Profile
Standards and Recommendations
Megestrol Acetate, 99%
Megestrol acetate, 98%