Estra-1,3,5(10)-triene-3,4-diol-17-one

Base Information

• Chemical Name: Estra-1,3,5(10)-triene-3,4-diol-17-one
• CAS No.: 3131-23-5
• Molecular Formula: C18H22 O3
• Molecular Weight: 286.371
• Metabolomics Workbench ID: 38785
• Mol file: 3131-23-5.mol

Synonyms:3,4-dihydroxy-1,3,5(10)-estratrien-17-one;4-hydroxyestrone

Chemical Property of Estra-1,3,5(10)-triene-3,4-diol-17-one

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 260-263°C
• Boiling Point: 468.2°Cat760mmHg
• PKA: 10.06±0.40(Predicted)
• Flash Point: 251.1°C
• PSA: 57.53000
• Density: 1.241g/cm³
• LogP: 3.52300
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 286.15689456
• Heavy Atom Count: 21
• Complexity: 448

Purity/Quality:

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

4-Hydroxy estrone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A reproductive hazard.
• Hazard Codes: A reproductive hazard.

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2=O)CCC4=C3C=CC(=C4O)O
• Isomeric SMILES: C[C@@]12CCC3C(C1CCC2=O)CCC4=C3C=CC(=C4O)O
• Uses: A metabolite of Estradiol

Technology Process of Estra-1,3,5(10)-triene-3,4-diol-17-one

There total 3 articles about Estra-1,3,5(10)-triene-3,4-diol-17-one 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: 47.0%

Estrone (53-16-7) → 4-hydroxyestrone (3131-23-5) + 2-hydroxyestrone (362-06-1,4735-38-0)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In methanol; chloroform; at -25 ℃; for 24h;

DOI:10.1016/j.tetlet.2005.03.060

Reference yield:

Estrone (53-16-7) → 4-hydroxyestrone (3131-23-5) + 2-hydroxyestrone (362-06-1,4735-38-0) + 16α-hydroxyestrone (566-76-7)

Guidance literature:

With cytochrome P₄₅₀ 1A₂; NADPH-generating system; In phosphate buffer; at 37 ℃; for 0.25h; pH=7.4; Further Variations:; Reagents; time; Enzyme kinetics;

DOI:10.1021/tx970217f

Reference yield:

4-Ethylphenol (123-07-9) + 3,4-estrone-o-quinone (40551-34-6) → 4-hydroxyestrone (3131-23-5) + (8R,9S,13S,14S)-1-(4-Ethyl-phenoxy)-3,4-dihydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one + (8R,9S,13S,14S)-1-((8R,9S,13S,14S)-4-Hydroxy-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yloxy)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthrene-3,4,17-trione

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/tx950146p

upstream raw materials:

Estrone

4-Ethylphenol

3,4-estrone-o-quinone

Downstream raw materials:

3-methoxy-4-hydroxy-1,3,5 ⁽¹⁰⁾-estratrien-17-one

4-methoxyestrone

3,4-Dimethoxy-1,3,5⁽¹⁰⁾-estratrien-17-one

3,4-estrone-o-quinone

Refernces

• 1、 Pezzella, Alessandro,Lista, Liliana,Napolitano, Alessandra,D'Ischia, Marco. "An expedient one-pot entry to catecholestrogens and other catechol compounds via IBX-mediated phenolic oxygenation". . p. 3541 - 3544. Retrieved 2007/10/03.
• 2、 Yamazaki, Hiroshi,Shaw, Peter M.,Guengerich, F. Peter,Shimada, Tsutomu. "Roles of cytochromes P450 1A2 and 3A4 in the oxidation of estradiol and estrone in human liver microsomes". . p. 659 - 665. Retrieved 2007/10/03.