(E)-4-Hydroxytamoxifen

Base Information

• Chemical Name: (E)-4-Hydroxytamoxifen
• CAS No.: 174592-47-3
• Molecular Formula: C26H29NO2
• Molecular Weight: 387.522
• European Community (EC) Number: 627-097-8
• UNII: AKE3PH0IML
• DSSTox Substance ID: DTXSID10169854
• Wikipedia: Afimoxifene
• Wikidata: Q27273974
• NCI Thesaurus Code: C975
• Pharos Ligand ID: QW9UK21GMCQ2
• ChEMBL ID: CHEMBL279301
• Mol file: 174592-47-3.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 (E)-4-Hydroxytamoxifen

Chemical Property:

• Vapor Pressure: 3.35E-11mmHg at 25°C
• Melting Point: 138-141°C
• Boiling Point: 514.4oC at 760 mmHg
• Flash Point: 264.9oC
• PSA: 32.70000
• Density: 1.092g/cm3
• LogP: 5.70170
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform
• 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:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC(=C(C1=CC=C(C=C1)O)C2=CC=C(C=C2)OCCN(C)C)C3=CC=CC=C3
• Isomeric SMILES: CC/C(=C(/C1=CC=C(C=C1)O)\C2=CC=C(C=C2)OCCN(C)C)/C3=CC=CC=C3
• Recent ClinicalTrials: Afimoxifene in Reducing the Risk of Breast Cancer in Women With Mammographically Dense Breast
• Recent EU Clinical Trials: A Randomized, Double-blind, Placebo Controlled Trial of 4-Hydroxytamoxifen Gel for Reducing Breast Tissue Density in Women with BI-RADS Breast Density Categories C or D
• Uses: A metabolite of Tamoxifen. A hydroxylated analogue of Tamoxifen (T006000) with anti-estrogenic properties.

Technology Process of (E)-4-Hydroxytamoxifen

There total 21 articles about (E)-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: 66.0%

2,2-Dimethyl-propionic acid 4-{(E)-1-[4-(2-dimethylamino-ethoxy)-phenyl]-2-phenyl-but-1-enyl}-phenyl ester (177748-19-5) → Z-1-<4-(2-dimethylaminoethoxy)phenyl>-1-(4-hydroxyphenyl)-2-phenyl-1-butene (68047-06-3,65213-48-1) + trans 4-hydroxytamoxifen (174592-47-3,65213-48-1)

Guidance literature:

With methyllithium; In tetrahydrofuran; diethyl ether; at -78 ℃; for 2h; Yields of byproduct given;

DOI:10.1021/jo952279l

Reference yield:

dimethyl amine (124-40-3) + E/Z-1-[4-(2-bromoethoxy)phenyl]-1-(4-hydroxyphenyl)-2-phenylbutene (147323-02-2) → Z-1-<4-(2-dimethylaminoethoxy)phenyl>-1-(4-hydroxyphenyl)-2-phenyl-1-butene (68047-06-3,65213-48-1) + trans 4-hydroxytamoxifen (174592-47-3,65213-48-1)

Guidance literature:

In tetrahydrofuran; at 60 ℃; for 43h;

Reference yield:

1-[4-(2-Dimethylamino-ethoxy)-phenyl]-2-phenyl-1-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-butan-1-ol (68047-08-5) → Z-1-<4-(2-dimethylaminoethoxy)phenyl>-1-(4-hydroxyphenyl)-2-phenyl-1-butene (68047-06-3,65213-48-1) + trans 4-hydroxytamoxifen (174592-47-3,65213-48-1)

Guidance literature:

With hydrogenchloride; In methanol; at 60 - 70 ℃; for 0.5h; Yield given. Yields of byproduct given;

DOI:10.1021/jm00148a020

upstream raw materials:

1-[4-(2-Dimethylamino-ethoxy)-phenyl]-2-phenyl-1-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-butan-1-ol

(Z)-1-<4-(2-chloroethoxy)phenyl>-1-<4-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>phenyl>-2-phenyl-1-butene

dimethyl amine

1-phenyl-propan-1-one

Refernces

• 1、 Salvador, J.-Pablo,Vila-Roca, Ester,Monfort, Núria,Ventura, Rosa,Marco, M.-Pilar. "New approach based on immunochemical techniques for monitoring of selective estrogen receptor modulators (SERMs) in human urine". . p. 147 - 152. Retrieved 2018.
• 2、 -. "TARGETED DRUG-FORMALDEHYDE CONJUGATES AND METHODS OF MAKING AND USING THE SAME". Page/Page column 94. . Retrieved 2008/06/13.