Estrone 3-hemisuccinate

Base Information

• Chemical Name: Estrone 3-hemisuccinate
• CAS No.: 58534-72-8
• Molecular Formula: C22H26O5
• Molecular Weight: 370.445
• European Community (EC) Number: 637-380-8
• ChEMBL ID: CHEMBL3116120
• DSSTox Substance ID: DTXSID80474523
• Nikkaji Number: J1.996.654B
• Wikidata: Q76422219
• Mol file: 58534-72-8.mol

Synonyms:Estrone 3-hemisuccinate;58534-72-8;4-[[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl]oxy]-4-oxobutanoic acid;ST056227;1,3,5(10)-Estratrien-3-ol-17-one hemisuccinate;SCHEMBL8903503;CHEMBL3116120;Estrone 3-hemisuccinate, ~95%;DTXSID80474523;AKOS024282437;4-((8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yloxy)-4-oxobutanoic acid

Chemical Property of Estrone 3-hemisuccinate

Chemical Property:

• PSA: 80.67000
• LogP: 3.88200
• Storage Temp.: 2-8°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 370.17802393
• Heavy Atom Count: 27
• Complexity: 628

Purity/Quality:

99% ^*data from raw suppliers

Estrone 3-hemisuccinate ~95% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22-40
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2=O)CCC4=C3C=CC(=C4)OC(=O)CCC(=O)O
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)OC(=O)CCC(=O)O

Technology Process of Estrone 3-hemisuccinate

There total 3 articles about Estrone 3-hemisuccinate 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: 98.0%

succinic acid anhydride (108-30-5) + Estrone (53-16-7) → estrone-3′-hemisuccinate (58534-72-8)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; at 20 ℃; for 42h;

DOI:10.1111/jphp.12736

Reference yield: 92.0%

3-hydroxy-1,3,5(10)-estratrien-17-one 3-<4-(2,2,2-trichloroethoxy)-4-oxobutanoate> (91378-54-0) → 3-hydroxy-1,3,5(10)-estradien-17-one 3-(3-carboxypropanoate) (58534-72-8)

Guidance literature:

With water; acetic acid; zinc; In tetrahydrofuran; for 4h; reaction in ice bath;

DOI:10.1135/cccc19840306

Reference yield:

estrone (53-16-7,474-84-0,517-06-6,1225-03-2,4413-09-6,4680-83-5,5285-27-8,15426-98-9,17337-44-9,19973-76-3,35937-97-4,35937-99-6,35938-00-2,94424-34-7,101976-76-5,107910-81-6) → 3-hydroxy-1,3,5(10)-estradien-17-one 3-(3-carboxypropanoate) (58534-72-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / N,N'-dicyclohexylcarbodiimide, 4-dimethylaminopyridine / benzene / 48 h / 18 °C

2: 92 percent / water, Zn powder, acetic acid / tetrahydrofuran / 4 h / reaction in ice bath

With dmap; water; acetic acid; dicyclohexyl-carbodiimide; zinc; In tetrahydrofuran; benzene;

DOI:10.1135/cccc19840306

upstream raw materials:

3-hydroxy-1,3,5(10)-estratrien-17-one 3-<4-(2,2,2-trichloroethoxy)-4-oxobutanoate>

estrone

succinic acid anhydride

Estrone

Downstream raw materials:

Estrone

Refernces

• 1、 Kurmi, Balak Das,Paliwal, Rishi,Paliwal, Shivani Rai. "Dual cancer targeting using estrogen functionalized chitosan nanoparticles loaded with doxorubicin-estrone conjugate: A quality by design approach". . p. 2881 - 2894. Retrieved 2020.
• 2、 -. "Glucagon superfamily peptides exhibiting nuclear hormone receptor activity". Page/Page column 249; 250. . Retrieved 2015/09/28.