(E)-4-Hydroxytamoxifen

Base Information

• Chemical Name: (E)-4-Hydroxytamoxifen
• CAS No.: 68392-35-8
• Molecular Formula: C26H29 N O2
• 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: 68392-35-8.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 (E)-4-Hydroxytamoxifen

Chemical Property:

• Melting Point: 135-144°C
• Boiling Point: 514.4±50.0 °C(Predicted)
• PKA: 9.38±0.15(Predicted)
• PSA: 32.70000
• Density: 1.092
• LogP: 5.70170
• Storage Temp.: Refrigerator
• Solubility.: methanol: soluble10mg/mL
• 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:

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

(E/Z)-4-HydroxyTamoxifen ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 63-20/21/22
• Safety Statements: 22-23-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

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 selective estrogen receptor modulator. (E/Z)-4-Hydroxy Tamoxifen is selective estrogen receptor modulator.

Technology Process of (E)-4-Hydroxytamoxifen

There total 19 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: 73.0%

C37H34BrNO7 → 4-hydroxytamoxifen (68392-35-8,65213-48-1)

Guidance literature:

With water; In methanol; for 0.0333333h; Quantum yield; Photolysis;

DOI:10.1021/acschembio.6b00999

Reference yield: 67.0%

(2-chloroethyl)dimethylamine hydrochloride (4584-46-7) + 1,1-bis(4-hydroxyphenyl)-2-phenyl-1-butene (91221-46-4) → 4-hydroxytamoxifen (68392-35-8,65213-48-1)

Guidance literature:

1,1-bis(4-hydroxyphenyl)-2-phenyl-1-butene; With caesium carbonate; In N,N-dimethyl-formamide; for 0.5h; Reflux;

(2-chloroethyl)dimethylamine hydrochloride; In N,N-dimethyl-formamide; at 120 ℃; for 7h;

DOI:10.1039/c3cc38957j

Reference yield: 31.0%

dimethyl amine (124-40-3) + E/Z-1-[4-(2-bromoethoxy)phenyl]-1-(4-hydroxyphenyl)-2-phenylbutene (147323-02-2) → 4-hydroxytamoxifen (68392-35-8,65213-48-1)

Guidance literature:

In tetrahydrofuran; at 60 ℃; for 43h;

DOI:10.1021/jm030352r

upstream raw materials:

dimethyl amine

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

phenylpropane

4-hydroxy-4'-methoxybenzophenone

Downstream raw materials:

C₆₅H₇₅N₄O₁₂PSi

(E,Z)-4-(1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl)phenyl trifluoromethanesulfonate

N,N-dimethyl-2-(4-(2-phenyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)but-1-en-1-yl)phenoxy)ethanamine

potassium [4-(1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl)phenyl]trifluoroboranuide

Refernces

• 1、 -. "ANTICANCER AGENT DELIVERY MOLECULE". . . Retrieved 2017/08/04.
• 2、 Ota, Yosuke,Itoh, Yukihiro,Kaise, Asako,Ohta, Kiminori,Endo, Yasuyuki,Masuda, Mitsuharu,Sowa, Yoshihiro,Sakai, Toshiyuki,Suzuki, Takayoshi. "Targeting Cancer with PCPA-Drug Conjugates: LSD1 Inhibition-Triggered Release of 4-Hydroxytamoxifen". . p. 16115 - 16118. Retrieved 2016/12/26.