4-Hydroxyestradiol

Base Information

• Chemical Name: 4-Hydroxyestradiol
• CAS No.: 5976-61-4
• Molecular Formula: C₁₈H₂₄O₃
• Molecular Weight: 288.387
• European Community (EC) Number: 637-368-2
• UNII: C3ZO03450E
• DSSTox Substance ID: DTXSID3022374
• Nikkaji Number: J353.576B
• Wikipedia: 4-Hydroxyestradiol
• Wikidata: Q27104901
• NCI Thesaurus Code: C120473
• Metabolomics Workbench ID: 35288
• ChEMBL ID: CHEMBL1412489
• Mol file: 5976-61-4.mol

Synonyms:4-hydroxyestradiol;4-hydroxyestradiol-17 alpha;4-hydroxyestradiol-17 beta

Chemical Property of 4-Hydroxyestradiol

Chemical Property:

• Vapor Pressure: 1.39E-09mmHg at 25°C
• Melting Point: >210oC (dec.)
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 468.6°C at 760 mmHg
• PKA: 10.07±0.60(Predicted)
• Flash Point: 220.6°C
• PSA: 60.69000
• Density: 1.248g/cm³
• LogP: 3.31480
• Storage Temp.: −20°C
• Solubility.: Ethanol (Slightly, Heated), Ethyl Acetate (Slightly, Heated), Methanol (Slightly
• XLogP3: 3.7
• 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

4-Hydroxy-17β-estradiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2O)CCC4=C3C=CC(=C4O)O
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4O)O

Technology Process of 4-Hydroxyestradiol

There total 3 articles about 4-Hydroxyestradiol 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: 42.0%

estradiol (50-28-2) → 4-Hydroxyestradiol (5976-61-4,72704-99-5) + 2-Hydroxyestradiol (362-05-0)

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:

estradiol (50-28-2) → 4-Hydroxyestradiol (5976-61-4,72704-99-5) + 2-Hydroxyestradiol (362-05-0) + Estriol (50-27-1,300853-07-0)

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:

1-O-(3,4-dihydroxy-1,3,5(10)-estratrien-17β-yl)-β-D-glucopyranosiduronic acid (90746-96-6) → D-glucuronic acid (6556-12-3,489-91-8,528-16-5,552-12-5,577-46-8,643-33-4,2240-07-5,6294-16-2,10133-02-5,18402-78-3,18968-14-4,21179-08-8,23018-83-9,33599-45-0,33599-46-1,46171-67-9,46171-69-1,46172-26-3,70021-34-0,71031-08-8,104195-06-4,106499-29-0,124817-72-7) + 4-Hydroxyestradiol (5976-61-4,72704-99-5)

Guidance literature:

With β-glucuronidase from Helix pomatia; In various solvent(s); at 37 ℃; for 24h; Product distribution; pH=5.2;

DOI:10.1248/cpb.34.179

upstream raw materials:

estradiol

1-O-(3,4-dihydroxy-1,3,5(10)-estratrien-17β-yl)-β-D-glucopyranosiduronic acid

Downstream raw materials:

4-methoxy-17β-estradiol

4-hydroxy-3-methoxyestra-1,3,5(10)-trien-17β-ol

4-hydroxyestradiol 3,4-dimethyl ether

17β-Estradiol-3,4-quinone

Refernces

• 1、 Jang, Hyun-Hee,Kim, Dong-Hyun,Ahn, Taeho,Yun, Chul-Ho. "Functional and conformational modulation of human cytochrome P450 1B1 by anionic phospholipids". experimental part. p. 143 - 150. Retrieved 2010/12/19.
• 2、 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.