82413-23-8

Basic information

• Product Name: 4Hydroxy Tamoxifen
• Synonyms: 4-[(1Z)-1-[[4-[2-(Dimethylamino)ethoxy]phenyl]phenylmethylene]propyl]phenol;4'-Hydroxy TaMoxifen (contains up to 10% E isoMer)
• CAS NO: 82413-23-8
• Molecular Formula: C₂₆H₂₉NO₂
• Molecular Weight: 387.51
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 82413-23-8.mol

Chemical Properties

• Melting Point: 150-153°C
• Appearance: /
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Dichloromethane, Methanol (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: 4Hydroxy Tamoxifen(CAS DataBase Reference)
• NIST Chemistry Reference: 4Hydroxy Tamoxifen(82413-23-8)
• EPA Substance Registry System: 4Hydroxy Tamoxifen(82413-23-8)

Safety Data

• Hazardous Substances Data: 82413-23-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4'-Hydroxy Tamoxifen is used as a pharmaceutical agent for its potential role in treating hormone receptor-positive breast cancer. Its higher affinity for estrogen receptors compared to Tamoxifen makes it a promising candidate for further research and development in cancer treatment.
Used in Cancer Research:
4'-Hydroxy Tamoxifen is used as a research tool to study the effects of estrogen receptor modulation on the growth and progression of hormone receptor-positive breast cancer. Its cytotoxic properties at specific concentrations provide valuable insights into the development of new therapeutic strategies for cancer treatment.
Used in Drug Metabolism Studies:
4'-Hydroxy Tamoxifen is used as a model compound in drug metabolism studies, particularly focusing on the role of cytochrome P450 enzymes (CYP2D6 and CYP2B6) in the biotransformation of Tamoxifen. Understanding the metabolic pathways and enzyme involvement can help optimize drug dosing and minimize adverse effects.

Upstream product

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• 24845-40-7 2-(4-methoxyphenyl)acetophenone 
• 75-03-6 ethyl iodide 
• 93790-54-6 [2-(4-iodophenoxy)ethyl]dimethylamine 
• 2633-75-2 ethylzinc chloride 
• 82413-28-3 2-(4-Hydroxy-phenyl)-1-phenyl-butan-1-one 
• 106-41-2 4-bromo-phenol 
• 35258-39-0 2-(p-methoxyphenyl)-1-phenylbutan-1-one 

Relevant articles and documents

Synthesis of tetrasubstituted alkenes by stereo- and regioselective stannyllithiation of diarylacetylenes

Addition of trimethylstannyllithium to a diarylacetylene takes place exclusively in an anti-fashion to produce a lithio vinylstannane intermediate. The regioselectivity of the addition is controlled by the steric and electronic property of the acetylene and reaches up to >99:1. The two newly formed C-metal bonds can be sequentially and stereospecifically transformed into two new C-C bonds as illustrated by stereoselective synthesis of 4-hydroxytamoxifen and its regioisomer. A tetraarylethene bearing different aryl groups can be synthesized similarly and cyclized to a substituted dibenzo[g,p]chrysene derivative via a palladium-catalyzed arylation reaction.

Estrogenic and Antiestrogenic Activity of Monophenolic Analogues of Tamoxifen, (Z)-2--N,N-dimethylethylamine

Five hydroxylated analogues of tamoxifen -N,N-dimethylethylamine> and its geometric isomer were prepared by reaction of protected hydroxy-α-ethyldeoxybenzoins with 4-phenylmagnesium bromide, followed by acid-catalyzed dehydration-deprotection and chromatographic separation of isomer mixtures.Estrogen receptor binding affinity and estrogenic and antiestrogenic activity of each of the compounds were determined in the rat, in comparison with 4-hydroxytamoxifen (2).The new compounds had a wide rangeof receptor binding affinities, with that of 3-hydroxytamoxifen (6c), the most strongly bound, approaching that of estradiol.The trans isomers 6a,b were more strongly bound than were the cis isomers 7a,b.Antiestrogenic activity was seen in all compounds except 7b.This was also true for estrogenic activity, except that in 6c this activity was also substantially reduced.Maximal antiestrogenic effectiveness of 6c occurred at a 10-fold greater daily dose (50 μg/rat) than that required for maximal effect of 2.