Levonorgestrel acetate

Base Information

• Chemical Name: Levonorgestrel acetate
• CAS No.: 13732-69-9
• Molecular Formula: C23H30O3
• Molecular Weight: 354.4825
• Hs Code.: 2937230000
• European Community (EC) Number: 604-013-8
• UNII: VF642934XZ
• DSSTox Substance ID: DTXSID301314299
• Nikkaji Number: J392.571D
• Wikipedia: Levonorgestrel_acetate
• Wikidata: Q27291802
• NCI Thesaurus Code: C77014
• Mol file: 13732-69-9.mol

Synonyms:3-ketonorgestimate;norgestrel acetate;norgestrel acetate, (17alpha)-isomer

Chemical Property of Levonorgestrel acetate

Chemical Property:

• PSA: 43.37000
• LogP: 4.45340
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 354.21949481
• Heavy Atom Count: 26
• Complexity: 710

Purity/Quality:

99.9% ^*data from raw suppliers

D-(-)-Norgestrel17-Acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC12CCC3C(C1CCC2(C#C)OC(=O)C)CCC4=CC(=O)CCC34
• Isomeric SMILES: CC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)OC(=O)C)CCC4=CC(=O)CC[C@H]34
• Uses: D-(-)-Norgestrel 17-Acetate is an impurity of Norgestrel (N689500), progestational and ovulation inhibiting steroid.

Technology Process of Levonorgestrel acetate

There total 20 articles about Levonorgestrel 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: 91.6%

acetic acid (64-19-7,77671-22-8) + levonorgestrel (797-63-7) → D-17β-acetoxy-13β-ethyl-17α-ethynyl-gon-4-en-3-one (13732-69-9)

Guidance literature:

With sodium carbonate; trifluoroacetic anhydride; In benzene; for 0.5h; Ambient temperature;

DOI:10.1016/0039-128X(85)90027-3

Reference yield: 89.3%

acetic anhydride (108-24-7) + levonorgestrel (797-63-7) → D-17β-acetoxy-13β-ethyl-17α-ethynyl-gon-4-en-3-one (13732-69-9)

Guidance literature:

With perchloric acid; In water; acetic acid; for 0.333333h;

Reference yield:

Acetic acid (8S,9R,10S,13R,14R,17S)-3-acetoxy-13-ethyl-17-ethynyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester → (+/-)17β-Acetoxy-13β-ethyl-17α-ethynylgon-4-en-3-one (13732-69-9,17092-15-8,18290-31-8)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; methanol;

upstream raw materials:

acetic anhydride

levonorgestrel

acetic acid

13β-ethyl-3-methoxy-17α-ethynyl-gona-2,5(10)-dien-17β-ol

Downstream raw materials:

norgestimate

Refernces

• 1、 -. "PROCESS FOR THE SYNTHESIS OF HIGH PURITY D-(17ALPHA)-13-ETHYL-17-HYDROXY-18,19-DINORPRE:GN-4-ENE-20-YNE-3-ONE-OXIME". Page/Page column 4. . Retrieved 2008/06/13.
• 2、 -. "3-Oximes of D-17α-ethynyl-19-nortestosterone esters and method". . . Retrieved 2008/06/13.