Afimoxifene

Base Information

• Chemical Name: Afimoxifene
• CAS No.: 68047-06-3
• Deprecated CAS: 65213-48-1,72732-26-4,76276-99-8,71880-76-7,76702-42-6,72732-26-4,76276-99-8
• Molecular Formula: C26H29 N O2
• Molecular Weight: 387.522
• European Community (EC) Number: 627-097-8,635-210-7
• UNII: 95K54647BZ
• DSSTox Substance ID: DTXSID7022384
• Nikkaji Number: J354.277G,J370.403C,J1.376.093D
• Wikipedia: Afimoxifene
• Wikidata: Q4689254
• NCI Thesaurus Code: C975
• Pharos Ligand ID: QW9G242RFJ8F
• Metabolomics Workbench ID: 56565
• ChEMBL ID: CHEMBL489
• Mol file: 68047-06-3.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 Afimoxifene

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 3.35E-11mmHg at 25°C
• Melting Point: 105-107°C
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 514.4°Cat760mmHg
• PKA: 10.35±0.15(Predicted)
• Flash Point: 264.9°C
• PSA: 32.70000
• Density: 1.092g/cm³
• LogP: 5.70170
• Storage Temp.: 2-8°C
• Solubility.: 95% ethanol: 20 mg/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:

97%, ^*data from raw suppliers

InSolution Tamoxifen, 4-Hydroxy-, ( Z)- - CAS 68047-06-3 - Calbiochem ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22-63
• 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 hydroxylated analogue of tamoxifen with anti-estrogenic properties. A metabolite of Tamoxifen. A metabolite of Tamoxifen (T006000). A hydroxylated analogue of Tamoxifen with anti-estrogenic properties. tamoxifen metabolite, anti-estrogen, see Tamoxifen 1,01038

Technology Process of Afimoxifene

There total 37 articles about Afimoxifene 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: 100.0%

(E)-1-[4-(benzyloxy)phenyl]-1-[4-(2-dimethylaminoethoxy)phenyl]-2-phenylbut-1-ene (109517-76-2) → Z-1-<4-(2-dimethylaminoethoxy)phenyl>-1-(4-hydroxyphenyl)-2-phenyl-1-butene (68047-06-3,65213-48-1)

Guidance literature:

With hydrogen; 10percent palladium on carbon; In ethyl acetate; for 2.5h; under 760.051 Torr;

DOI:10.1021/jo0255328

Reference yield: 81.0%

C37H36N3O3(1+)*CH3O3S(1-) → C11H7N2O2(1-) + Z-1-<4-(2-dimethylaminoethoxy)phenyl>-1-(4-hydroxyphenyl)-2-phenyl-1-butene (68047-06-3,65213-48-1)

Guidance literature:

In ethanol; pH=7.2; UV-irradiation;

DOI:10.1021/jacs.7b06363

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

upstream raw materials:

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

1-bromo-1-(4-<(2-tetrahydropyranyl)oxy>phenyl)-2-phenyl-1-butene

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

dimethyl amine

Downstream raw materials:

4-((E)-1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenyl 4-(-2-((4-methoxy-1H,1'H-[2,2'-bipyrrol]-5-yl)methylene)-3,5-dimethyl-2H-pyrrol-4-yl)-4-oxobutanoate

4-((E)-1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenyl 10-((Z)-2-((4-methoxy-1H,1'H-2,2'-bipyrrol-5-yl)methylene)-3,5-dimethyl-2H-pyrrol-4-yl)-10-oxodecanoate

trans 4-hydroxytamoxifen

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 2018/05/04.
• 2、 -. "Methods for Determining the Oncogenic Condition of Cell, Uses Thereof, and Methods for Treating Cancer". . . Retrieved 2017/07/14.