Pricing Availability   Qty
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)
Citations (5)
Reviews (1)
Pathways (1)

Biological Activity for (Z)-4-Hydroxytamoxifen

(Z)-4-Hydroxytamoxifen is an estrogen receptor antagonist (IC50 = 27 μM). (Z)-4-Hydroxytamoxifen is a Tamoxifen (Cat. No. 0999) metabolite; that exhibits greater potency than the parent compound. (Z)-4-Hydroxytamoxifen also activates intein-linked inactive Cas9, reducing off-target CRISPR-mediated gene editing; system has ~25-fold higher specificity than wtCas9. (Z)-4-Hydroxytamoxifen binds to voltage-gated sodium channels, near the intracellular gate and inhibits the sodium current by delaying channel recovery from the inactivated state (IC50 values are 297 nM and 2.1 µM for NavM and human Nav, respectively in HEK cells); this inhibition is independent of estrogen receptor modulation. Chemotherapeutic agent.

Technical Data for (Z)-4-Hydroxytamoxifen

M. Wt 387.51
Formula C26H29NO2
Storage Store at +4°C
Purity ≥98% (HPLC)
CAS Number 68047-06-3
PubChem ID 449459
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.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data for (Z)-4-Hydroxytamoxifen

Solvent Max Conc. mg/mL Max Conc. mM
DMSO 38.75 100
ethanol 7.75 20

Preparing Stock Solutions for (Z)-4-Hydroxytamoxifen

The following data is based on the product molecular weight 387.51. Batch specific molecular weights may vary from batch to batch due to the degree 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

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.


Dilution Calculator

Calculate the dilution required to prepare a stock solution.

Product Datasheets for (Z)-4-Hydroxytamoxifen

Certificate of Analysis / Product Datasheet
Select another batch:

References for (Z)-4-Hydroxytamoxifen

References are publications that support the biological activity of the product.

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

Desta et al (2004) Comprehensive evaluation of tamox. 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

Seeger et al (2004) Inhibition of human breast cancer cell proliferation with estradiol metabolites is as effective as with tamoxifen. Horm.Metab.Res. 36 277 PMID: 15156405

Sula et al (2021) A tamoxifen receptor within a voltage-gated sodium channel. Mol.Cell. 81 1160 PMID: 33503406

If you know of a relevant reference for (Z)-4-Hydroxytamoxifen, please let us know.

View Related Products by Target

View Related Products by Product Action

View all Estrogen and Related Receptor Modulators

Keywords: (Z)-4-Hydroxytamoxifen, (Z)-4-Hydroxytamoxifen supplier, estrogen, receptors, antagonists, ER, 4-hydroxy-TAM, antiestrogens, antioestrogens, SERM, selective, modulators, CRISPR, Cas9-intein, 4-OH-TAM, Estrogen, and, Related, Receptors, Reagents, 3412, Tocris Bioscience

5 Citations for (Z)-4-Hydroxytamoxifen

Citations are publications that use Tocris products. Selected citations for (Z)-4-Hydroxytamoxifen include:

Candelaria et al (2015) Alcohol Regulates Genes that Are Associated with Response to Endocrine Therapy and Attenuates the Actions of tamox. in Breast Cancer Cells. PLoS One 10 e0145061 PMID: 26661278

Ito et al (2017) PTK6 regulates growth and survival of endocrine therapy-resistant ER+ breast cancer cells. NPJ Breast Cancer 3 45 PMID: 29167821

Lee et al (2017) MTA1 is a novel regulator of autophagy that induces TAX resistance in breast cancer cells. Autophagy 14 812 PMID: 29130361

Chatterjee et al (2019) Paracrine Crosstalk between Fibroblasts and ER+ Breast Cancer Cells Creates an IL1β-Enriched Niche that Promotes Tumor Growth. iScience 19 388 PMID: 31419632

Do you know of a great paper that uses (Z)-4-Hydroxytamoxifen from Tocris? Please let us know.

Reviews for (Z)-4-Hydroxytamoxifen

Average Rating: 5 (Based on 1 Review.)

5 Star
4 Star
3 Star
2 Star
1 Star

Have you used (Z)-4-Hydroxytamoxifen?

Submit a review and receive an Amazon gift card.

$50/€35/£30/$50CAN/¥300 Yuan/¥5000 Yen for first to review with an image

$25/€18/£15/$25CAN/¥75 Yuan/¥1250 Yen for a review with an image

$10/€7/£6/$10 CAD/¥70 Yuan/¥1110 Yen for a review without an image

Submit a Review

Filter by:

4-hydroxytamoxifen for TRAPing cells.
By Anonymous on 05/23/2019
Assay Type: In Vivo
Species: Mouse

used for tamoxifen TRAPing using ERT-cre mice. given 3hrs post behavior. single dose was sufficient for recombination

.5mg/ml dissolved in 1% tween 80 and 2.5% DMSO, injected 5mg/kg i.p.

review image

Pathways for (Z)-4-Hydroxytamoxifen

Estrogen Signaling Pathway

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.