4'-Hydroxytamoxifen

Base Information

• Chemical Name: 4'-Hydroxytamoxifen
• CAS No.: 82413-23-8
• Molecular Formula: C26H29 N O2
• Molecular Weight: 387.522
• DSSTox Substance ID: DTXSID00873019
• Nikkaji Number: J703.840B
• Wikidata: Q27073761
• Pharos Ligand ID: TSA98R1RFHD6
• ChEMBL ID: CHEMBL10041
• Mol file: 82413-23-8.mol

Synonyms:4'-hydroxytamoxifen;4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol;4-hydroxy-tamoxifen;4-hydroxytamoxifen;4-hydroxytamoxifen, (E)-isomer;4-hydroxytamoxifen, (Z)-isomer;4-monohydroxytamoxifen;4-OHT hydrotamoxifen;4OH-tamoxifen;afimoxifene;hydroxytamoxifen;ICI 79280;monohydroxytamoxifen;para-hydroxytamoxifen;phenol, 4-((1Z)-1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenyl-1-buten-1-yl)-;phenol, 4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenyl-1-butenyl)-;phenol, 4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenyl-1-butenyl)-,;tamoxifen metabolite B

Chemical Property of 4'-Hydroxytamoxifen

Chemical Property:

• Melting Point: 150-153°C
• PSA: 32.70000
• LogP: 5.70170
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Dichloromethane, Methanol (Slightly)
• XLogP3: 6.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 387.219829168
• Heavy Atom Count: 29
• Complexity: 493

Purity/Quality:

> 95% ^*data from raw suppliers

4’-HydroxyTamoxifen(containsupto10%Eisomer) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=C(C1=CC=CC=C1)C2=CC=C(C=C2)OCCN(C)C)C3=CC=C(C=C3)O
• Isomeric SMILES: CC/C(=C(\C1=CC=CC=C1)/C2=CC=C(C=C2)OCCN(C)C)/C3=CC=C(C=C3)O
• Description: 4’-hydroxy Tamoxifen is one of five main phase I metabolites of tamoxifen , a well-known estrogen receptor antagonist in breast but partial estrogen receptor agonist in endometrium. 4’-hydroxy Tamoxifen is a product of cytochrome P450 (CYP)2D6 and CYP2B6 activity. With the addition of a hydroxyl group, 4’-hydroxy tamoxifen has been shown to have a higher affinity for estrogen receptors compared to tamoxifen. At 10-100 μM, 4’-hydroxy tamoxifen is cytotoxic, in a non-apoptotic manner, to HEC-1B and HEC-1A human endometrial adenocarcinoma cell lines.

Technology Process of 4'-Hydroxytamoxifen

There total 7 articles about 4'-Hydroxytamoxifen 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:

ethylzinc chloride (2633-75-2) + [2-(4-iodophenoxy)ethyl]dimethylamine (93790-54-6) + (4-methoxymethoxy)phenylphenylacetylene → Z-1-<4-(2-dimethylaminoethoxy)phenyl>-1-(4-hydroxyphenyl)-2-phenyl-1-butene (68047-06-3,65213-48-1) + (Z)-4-hydroxytamoxifen (82413-23-8)

Guidance literature:

(4-methoxymethoxy)phenylphenylacetylene; With (trimethylstannyl)lithium; In tetrahydrofuran; hexane; at 0 ℃; for 3h; Inert atmosphere;

With zinc(II) chloride; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

ethylzinc chloride; [2-(4-iodophenoxy)ethyl]dimethylamine; stereoselective reaction; Further stages;

DOI:10.1021/ja1059119

Reference yield:

ethyl iodide (75-03-6) + [2-(4-iodophenoxy)ethyl]dimethylamine (93790-54-6) + (4-methoxymethoxy)phenylphenylacetylene → Z-1-<4-(2-dimethylaminoethoxy)phenyl>-1-(4-hydroxyphenyl)-2-phenyl-1-butene (68047-06-3,65213-48-1) + (Z)-4-hydroxytamoxifen (82413-23-8)

Guidance literature:

(4-methoxymethoxy)phenylphenylacetylene; With (trimethylstannyl)lithium; In tetrahydrofuran; hexane; at 0 ℃; for 3h; Inert atmosphere;

ethyl iodide; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 3h; Inert atmosphere;

[2-(4-iodophenoxy)ethyl]dimethylamine; stereoselective reaction; Further stages;

DOI:10.1021/ja1059119

Reference yield:

2-(4-methoxyphenyl)acetophenone (24845-40-7) → (Z)-4-hydroxytamoxifen (82413-23-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH / 1.) DMF, 2.) DMF

2: 82 percent / 48percent aq. HBr, acetic acid / 4 h / Heating

3: 98percent H₂SO₄ / 12 h / Ambient temperature

4: 1.) C₂H₅MgBr, 3.) HCl

With hydrogenchloride; sulfuric acid; ethylmagnesium bromide; hydrogen bromide; sodium hydride; acetic acid;

DOI:10.1021/jm00351a010

upstream raw materials:

[2-(4-bromophenoxy)ethyl]dimethylamine

1-Phenyl-2-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-butan-1-one

2-(4-methoxyphenyl)acetophenone

4-bromo-phenol

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