alpha-Hydroxytamoxifen

Base Information

• Chemical Name: alpha-Hydroxytamoxifen
• CAS No.: 97151-02-5
• Molecular Formula: C26H29NO2
• Molecular Weight: 387.522
• Hs Code.: 2922509090
• DSSTox Substance ID: DTXSID501315817
• Nikkaji Number: J707.465D,J1.376.094B
• Wikidata: Q27149596
• Metabolomics Workbench ID: 78629
• ChEMBL ID: CHEMBL1908109
• Mol file: 97151-02-5.mol

Synonyms:alpha-hydroxytamoxifen

Chemical Property of alpha-Hydroxytamoxifen

Chemical Property:

• Vapor Pressure: 3.17E-12mmHg at 25°C
• Melting Point: 115-119oC
• Boiling Point: 533.8°Cat760mmHg
• PKA: 14.13±0.20(Predicted)
• Flash Point: 276.6°C
• PSA: 32.70000
• Density: 1.094g/cm³
• LogP: 5.70170
• Storage Temp.: Amber Vial, -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 387.219829168
• Heavy Atom Count: 29
• Complexity: 495

Purity/Quality:

97% ^*data from raw suppliers

(E)-α-HydroxyTamoxifen ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=C(C1=CC=CC=C1)C2=CC=C(C=C2)OCCN(C)C)C3=CC=CC=C3)O
• Isomeric SMILES: CC(/C(=C(\C1=CC=CC=C1)/C2=CC=C(C=C2)OCCN(C)C)/C3=CC=CC=C3)O
• Description: Tamoxifen is a selective estrogen receptor (ER) modulator that is widely used in the therapeutic and chemopreventive treatment of breast cancer. Although it is an antagonist of ER action in breast tissue, it acts as an ER agonist in bone and blood vessels and a partial ER agonist in uterine tissues. α-hydroxy Tamoxifen is a reactive metabolite of tamoxifen that is formed by the action of cytochrome P450 3A4 in human liver. It can be further converted into genotoxic DNA adducts though a mechanism involving reversible O-sulfonation of the hydroxyl moiety, which in rats has been linked with hepatocarcinoma.
• Uses: A metabolite of the chemotherapeutic drug tamoxifen. Exhibits a more potent estrogen agonist/antagonist activity than the parent drug. Also active as an intramembranous inhibitor of lipid peroxidation. A metabolite of the chemotherapeutic drug Tamoxifen (T006000). Exhibits a more potent estrogen agonist/antagonist activity than the parent drug. Also active as an intramembranous inhibitor of lipid peroxidation.

Technology Process of alpha-Hydroxytamoxifen

There total 4 articles about alpha-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: 29.0%

(E,Z)-4-[4-(2-dimethylaminoethoxy)phenyl]-3,4-diphenyl-but-3-en-2-one (556834-76-5) → (E)-(+/-)-alpha-Hydroxytamoxifen (97151-02-5) + (Z)-(+/-)-alpha-Hydroxytamoxifen (97170-41-7)

Guidance literature:

(E,Z)-4-[4-(2-dimethylaminoethoxy)phenyl]-3,4-diphenyl-but-3-en-2-one; With methanol; cerium(III) chloride heptahydrate; at 25 ℃; for 0.5h;

With sodium tetrahydroborate; at 25 ℃; for 1h;

DOI:10.1021/acs.orglett.7b03223

Reference yield:

trans-(E)-1-bromo-2-<4-<2-(dimethylamino)ethoxy>phenyl>-1,2-diphenylethene (19118-19-5) → E,Z-1-<4-<2-(dimethylamino)ethoxy>phenyl>-1,2-diphenylethene (19957-51-8) + (E)-(+/-)-alpha-Hydroxytamoxifen (97151-02-5) + (Z)-(+/-)-alpha-Hydroxytamoxifen (97170-41-7)

Guidance literature:

With n-butyllithium; acetaldehyde; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, -78 deg C to 0 deg C, 20 min;

DOI:10.1021/jm00148a020

Reference yield:

trans-(E)-1-bromo-2-<4-<2-(dimethylamino)ethoxy>phenyl>-1,2-diphenylethene (19118-19-5) + acetaldehyde (75-07-0,9002-91-9) → E,Z-1-<4-<2-(dimethylamino)ethoxy>phenyl>-1,2-diphenylethene (19957-51-8) + (E)-(+/-)-alpha-Hydroxytamoxifen (97151-02-5) + (Z)-(+/-)-alpha-Hydroxytamoxifen (97170-41-7)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, -78 deg C to 0 deg C, 20 min;

DOI:10.1021/jm00148a020

upstream raw materials:

trans-(E)-1-bromo-2-<4-<2-(dimethylamino)ethoxy>phenyl>-1,2-diphenylethene

acetaldehyde

trans-α-acetoxytamoxifen

(E,Z)-4-[4-(2-dimethylaminoethoxy)phenyl]-3,4-diphenyl-but-3-en-2-one

Downstream raw materials:

(E)-4-{4-[2-(N-Ethoxycarbonyl-N-methylamino)ethoxy]phenyl}-3,4-diphenyl-3-buten-2-ol

2-[2-{(E)-4-(4-(2-dimethylaminoethoxy)phenyl)-3,4-diphenyl-but-3-enyl}]isoindole-1,3-dione

[2-{(E)-4-(4-(2-dimethylaminoethoxy)phenyl)-3,4-diphenyl but-3-enyl}]amine

alpha-Hydroxy-N-desmethyltamoxifen