(Z)-4-Hydroxytamoxifen

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Cat.No. 3412 - (Z)-4-Hydroxytamoxifen | C26H29NO2 | CAS No. 68047-06-3
Description: Metabolite of tamoxifen (Cat. No. 0999)
Alternative Names: 4-OH-TAM
Chemical Name: 4-[(1Z)-1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]phenol
Purity: ≥98% (HPLC)
Datasheet
Citations
Literature
Pathways

Biological Activity

Estrogen receptor antagonist. Tamoxifen (Cat. No. 0999) metabolite; exhibits greater potency than the parent compound. Chemotherapeutic agent. Also activates intein-linked inactive Cas9, reducing off-target CRISPR-mediated gene editing; system has ~25-fold higher specificity than wtCas9.

Technical Data

M. Wt 387.51
Formula C26H29NO2
Storage Store at +4°C
Purity ≥98% (HPLC)
CAS Number 68047-06-3
PubChem ID 449459
InChI Key TXUZVZSFRXZGTL-QPLCGJKRSA-N
Smiles CC\C(C3=CC=CC=C3)=C(C2=CC=C(OCCN(C)C)C=C2)/C1=CC=C(O)C=C1

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 38.75 100
ethanol 19.38 50

Preparing Stock Solutions

The following data is based on the product molecular weight 387.51. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.58 mL 12.9 mL 25.81 mL
5 mM 0.52 mL 2.58 mL 5.16 mL
10 mM 0.26 mL 1.29 mL 2.58 mL
50 mM 0.05 mL 0.26 mL 0.52 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Jordan et al (1977) A monohydroxylated metabolite of tamoxifen with potent antioestrogenic activity. J.Endocrinology 75 305 PMID: 591813

Desta et al (2004) Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: Prominent roles for CYP3A and CYP2D6. J.Pharm.Exp.Ther. 310 1062 PMID: 15159443

Yu and Forman (2003) Simple and efficient production of (Z)-4-hydroxytamoxifen, a potent estrogen receptor modulator. J.Org.Chem. 68 9489 PMID: 14629178

Davis et al (2015) Small molecule-triggered Cas9 protein with improved genome-editing specificity. Nat.Chem.Biol. 11 316 PMID: 25848930


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View all Estrogen and Related Receptor Modulators

Keywords: estrogen receptors antagonists ER 4-hydroxy-TAM antiestrogens antioestrogens SERM selective modulators CRISPR Cas9-intein 4-OH-TAM Estrogen and Related Receptors

Citations for (Z)-4-Hydroxytamoxifen

Citations are publications that use Tocris products.

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Literature in this Area

Cancer

Cancer Research Product Guide

A collection of over 750 products for cancer research, the guide includes research tools for the study of:

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  • Epigenetics in Cancer
  • Receptor Signaling
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Nuclear Receptors

Nuclear Receptors Product Listing

A collection of over 150 products for key nuclear receptors, the listing includes research tools for the study of:

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Pathways for (Z)-4-Hydroxytamoxifen

Estrogen

Estrogen Signaling Pathway

Estrogen is a steroid hormone that is responsible for the regulation of growth, differentiation and function of the reproductive system. Estrogen signaling is often dysregulated in breast cancer and osteoporosis.

Protocols

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