Endoxifen, (E)-

Base Information

• Chemical Name: Endoxifen, (E)-
• CAS No.: 110025-28-0
• Molecular Formula: C25H27 N O2
• Molecular Weight: 373.495
• Hs Code.: 2922509090
• European Community (EC) Number: 808-709-4
• NSC Number: 750182
• UNII: HB2U71MNOT
• DSSTox Substance ID: DTXSID70150869
• Nikkaji Number: J2.971.762A
• Wikidata: Q26998030
• Mol file: 110025-28-0.mol

Synonyms:4-hydroxy-N-demethyltamoxifen;4-hydroxy-N-desmethyltamoxifen;4-hydroxy-N-desmethyltamoxifen, (Z)-isomer;endoxifen;Z-endoxifen

Chemical Property of Endoxifen, (E)-

Chemical Property:

• Vapor Pressure: 2.1E-11mmHg at 25°C
• Melting Point: 63-72°C
• Boiling Point: 519.3°Cat760mmHg
• PKA: 9.38±0.15(Predicted)
• Flash Point: 267.9°C
• PSA: 41.49000
• Density: 1.099g/cm³
• LogP: 5.75040
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform, Dichloromethane, DMSO, Methanol
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 373.204179104
• Heavy Atom Count: 28
• Complexity: 467

Purity/Quality:

98%Min ^*data from raw suppliers

N-Desmethyl-4-hydroxyTamoxifen(approx.1:1E/ZMixture) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=C(C1=CC=C(C=C1)O)C2=CC=C(C=C2)OCCNC)C3=CC=CC=C3
• Isomeric SMILES: CC/C(=C(/C1=CC=C(C=C1)O)\C2=CC=C(C=C2)OCCNC)/C3=CC=CC=C3
• Uses: A novel active metabolite of the anti-cancer drug Tamoxifen. It showed potent ER binding property, blocked estrogen stimulated growth of breast cancer cell and half maximal inhibition of estrogen responsive gene expression in ER pos. human breast ca A novel active metabolite of the anti-cancer drug Tamoxifen (T006000). It showed potent ER binding property, blocked estrogen stimulated growth of breast cancer cell and half maximal inhibition of estrogen responsive gene expression in ER pos. human breast cancer cell line.

Technology Process of Endoxifen, (E)-

There total 20 articles about Endoxifen, (E)- 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: 91.0%

methylamine (74-89-5) + E/Z-1-[4-(2-bromoethoxy)phenyl]-1-(4-hydroxyphenyl)-2-phenylbutene (147323-02-2) → (E/Z)-4-[1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]-phenol (110025-28-0)

Guidance literature:

In tetrahydrofuran; at 60 ℃; for 48h;

DOI:10.1021/jm030352r

Reference yield: 91.0%

2-(4-(1-(4-benzyloxyphenyl)-2-phenylbut-1-en-1-yl)phenoxy)-N-methylethan-1-amine → (E/Z)-4-[1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]-phenol (110025-28-0)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 ℃; for 0.5h;

Reference yield:

phenylpropane (103-65-1) → (E/Z)-4-[1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]-phenol (110025-28-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium tert-butoxide; n-butyllithium; tetramethylethylenediamine / hexane; tetrahydrofuran / 0.5 h / 20 °C

1.2: 97 percent / hexane; tetrahydrofuran / 4.5 h / -78 - 20 °C

2.1: 93 percent / aq. hydrochloric acid / ethanol; CH₂Cl₂ / Heating

3.1: 90 percent / aq. sodium hydroxide; tetrabutylammonium hydrogen sulfate / 18 h / 20 °C

4.1: 57 percent / boron tribromide / CH₂Cl₂ / 4.5 h

5.1: 91 percent / tetrahydrofuran / 48 h / 60 °C

With hydrogenchloride; sodium hydroxide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; potassium tert-butylate; tetra(n-butyl)ammonium hydrogensulfate; boron tribromide; In tetrahydrofuran; ethanol; hexane; dichloromethane;

DOI:10.1021/jm030352r

upstream raw materials:

methylamine

E/Z-1-[4-(2-bromoethoxy)phenyl]-1-(4-hydroxyphenyl)-2-phenylbutene

phenylpropane

4-(methoxymethoxy)-4'-methoxybenzophenone

Downstream raw materials:

E/Z-N-[2-hydroxy-5-({2-[(2-{4-[1-(4-hydroxyphenyl)-2-phenylbut-1-enyl]phenoxy}ethyl)methylamino]ethoxyimino}methyl)benzamide]doxorubicin

trans-Endoxifen

endoxifen ethyl formate

Refernces

• 1、 -. "NOVEL COMPOUNDS HAVING ESTROGEN RECEPTOR ALPHA DEGRADATION ACTIVITY AND USES THEREOF". Paragraph 0575; 0578. . Retrieved 2020/06/08.
• 2、 Burke, Patrick J.,Koch, Tad H.. "Design, Synthesis, and Biological Evaluation of Doxorubicin-Formaldehyde Conjugates Targeted to Breast Cancer Cells". . p. 1193 - 1206. Retrieved 2007/10/03.