1-Dehydromegesterol acetate

Base Information

• Chemical Name: 1-Dehydromegesterol acetate
• CAS No.: 982-89-8
• Molecular Formula: C₂₄H₃₀O₄
• Molecular Weight: 382.5
• UNII: 97Y3D0E49L
• Nikkaji Number: J579.726H
• Wikidata: Q27272045
• Mol file: 982-89-8.mol

Synonyms:1-Dehydromegesterol acetate;982-89-8;UNII-97Y3D0E49L;97Y3D0E49L;6-Methyl-3,20-dioxopregna-1,4,6-trien-17-yl acetate;Megestrol acetate specified impurity E [EP];Pregna-1,4,6-triene-3,20-dione, 17-(acetyloxy)-6-methyl-;[(8R,9S,10R,13S,14S,17R)-17-acetyl-6,10,13-trimethyl-3-oxo-9,11,12,14,15,16-hexahydro-8H-cyclopenta[a]phenanthren-17-yl] acetate;SCHEMBL6693949;MEGESTROL ACETATE IMPURITY E [EP IMPURITY];Q27272045

Chemical Property of 1-Dehydromegesterol acetate

Chemical Property:

• Melting Point: 225-227 °C(Solv: acetone (67-64-1); ethyl ether (60-29-7))
• Boiling Point: 509.0±50.0 °C(Predicted)
• Density: 1.17±0.1 g/cm3(Predicted)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 382.21440943
• Heavy Atom Count: 28
• Complexity: 862

Purity/Quality:

92%+ ^*data from raw suppliers

1-DehydromegesterolAcetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC2C3CCC(C3(CCC2C4(C1=CC(=O)C=C4)C)C)(C(=O)C)OC(=O)C
• Isomeric SMILES: CC1=C[C@H]2[C@@H]3CC[C@@]([C@]3(CC[C@@H]2[C@@]4(C1=CC(=O)C=C4)C)C)(C(=O)C)OC(=O)C
• Uses: 1-Dehydromegesterol Acetate (Megestrol Acetate EP Impurity E) is an impurity of Megestrol Acetate (M208050), is an orally active progestogen; formerly used in combinations as oral contraceptive (1). Used in hormone-replacement and anti-cancer therapies as well as birth control in animals (2).

Technology Process of 1-Dehydromegesterol acetate

There total 10 articles about 1-Dehydromegesterol acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

Megestrol acetate (595-33-5) → 17-acetoxy-6-methyl-pregna-1,4,6-triene-3,20-dione (982-89-8)

Guidance literature:

With pyridine; selenium(IV) oxide; tert-butyl alcohol;

DOI:10.1021/ja01523a055

Reference yield:

Medroxyprogesterone acetate (71-58-9) → 17-acetoxy-6-methyl-pregna-1,4,6-triene-3,20-dione (982-89-8)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrachloro-<1,4>benzoquinone

2: SeO₂; pyridine; tert-butyl alcohol

With pyridine; selenium(IV) oxide; chloranil; tert-butyl alcohol;

DOI:10.1021/ja01523a055

Reference yield:

3β-acetoxy-17α-hydroxy-5-pregnen-20-one (1863-39-4) → 17-acetoxy-6-methyl-pregna-1,4,6-triene-3,20-dione (982-89-8)

Guidance literature:

Multi-step reaction with 9 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

9: SeO₂; pyridine; tert-butyl alcohol

With pyridine; chromium(VI) oxide; hydrogenchloride; selenium(IV) oxide; Perbenzoic acid; diethyl ether; chloroform; sulfuric acid; chloranil; toluene-4-sulfonic acid; acetic acid; tert-butyl alcohol; benzene;

DOI:10.1021/ja01523a055

upstream raw materials:

Megestrol acetate

Medroxyprogesterone acetate

3β-acetoxy-17α-hydroxy-5-pregnen-20-one

Medroxyprogesterone