Epiestriol

Base Information

• Chemical Name: Epiestriol
• CAS No.: 547-81-9
• Molecular Formula: C18H24 O3
• Molecular Weight: 288.387
• European Community (EC) Number: 208-937-9
• NSC Number: 26646
• UNII: 8XZ32LI44K
• DSSTox Substance ID: DTXSID10894790
• Nikkaji Number: J6.440H
• Wikipedia: Epiestriol
• Wikidata: Q24897913
• NCI Thesaurus Code: C80787
• Metabolomics Workbench ID: 35276
• ChEMBL ID: CHEMBL1908074
• Mol file: 547-81-9.mol

Synonyms:(16alpha,17beta)-Estra-1,3,5(10)-Triene-3,16,17-Triol;(16beta,17beta)-Estra-1,3,5(10)-Triene-3,16,17-Triol;16 alpha Hydroxy Estradiol;16-alpha-Hydroxy-Estradiol;16alpha,17beta Estriol;16alpha,17beta-Estriol;16beta Hydroxy Estradiol;16beta-Hydroxy-Estradiol;Epiestriol;Estra-1,3,5(10)-Triene-3,16beta,17beta-Triol;Estriol;Ovestin

Chemical Property of Epiestriol

Chemical Property:

• Vapor Pressure: 1.34E-09mmHg at 25°C
• Melting Point: 289-291oC
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 469°C at 760 mmHg
• PKA: 10.25±0.70(Predicted)
• Flash Point: 220.8°C
• PSA: 60.69000
• Density: 1.255g/cm³
• LogP: 2.58000
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly, Heated)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 288.17254462
• Heavy Atom Count: 21
• Complexity: 411

Purity/Quality:

98%,99%, ^*data from raw suppliers

16-Epiestriol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CC(C2O)O)CCC4=C3C=CC(=C4)O
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@@H]([C@@H]2O)O)CCC4=C3C=CC(=C4)O
• Uses: 16-Epiestriol is a metabolite of Estradiol.

Technology Process of Epiestriol

There total 21 articles about Epiestriol 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: 66.0%

2,4-dibromo-3,17β-dihydroxyestra-1,3,5(10)-trien-16-one (19590-52-4) → epiestriol (547-81-9,300853-07-0)

Guidance literature:

With sodium tetrahydroborate; palladium dichloride; In methanol; at 0 ℃; for 2h;

Reference yield: 37.0%

Estriol (50-27-1,300853-07-0) → epiestriol (547-81-9,300853-07-0)

Guidance literature:

Estriol; With dihydroxy-methyl-borane; tetrabutylphosphonium decatungstate; diphenyldisulfane; In acetonitrile; tert-butyl alcohol; for 36h; Cooling with ice; UV-irradiation; Inert atmosphere; Sealed tube;

With pinanediol; potassium carbonate; In acetonitrile; tert-butyl alcohol; for 24h; diastereoselective reaction;

DOI:10.1021/jacs.1c11552

Reference yield:

→ estriol (50-27-1,547-81-9,651-50-3,793-89-5,1228-72-4,21610-95-7,300853-07-0)

Guidance literature:

Die radioaktive Verbindung findet sich als 3-Glucuronid im Harn v. Menschen nach Verabfolgung v. <7α-³H>-Androstenolon-<¹⁴C>glucuronid;

upstream raw materials:

16-oxoestradiol

3,16β-diacetoxyestra-1,3,5(10)-trien-17-one

2,4-dibromo-3,17β-dihydroxyestra-1,3,5(10)-trien-16-one

1-methyl-4-nitrosobenzene

Downstream raw materials:

3-benzyloxy-16α,17β-dihydroxy-1,3,5(10)-estratriene

3-O-(2-propenyl)epiestriol

Refernces

• 1、 Numazawa, Mitsuteru,Nagaoka, Masao,Tsuji, Masachika,Osawa, Yoshio. "Novel and Efficient Synthesis of Estriol and its 16-Glucuronide via 2,4,16α-Tribromoestrone". . p. 121 - 125. Retrieved 2007/10/02.
• 2、 OZON,BREUER. "STUDIES ON THE METABOLISM OF STEROID HORMONES IN VERTEBRATES. II.". . p. 282 - 285. Retrieved 2007/10/13.