(Z)-4-Hydroxytamoxifen

Name: ( Z )-4-Hydroxytamoxifen
Brand: Tocris Bioscience
SKU: 3412
Rating: 5 (1 reviews)

Tocris Bioscience, part of Bio-Techne | Catalog # 3412

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Citations (59)

COA / SDS

Metabolite of tamoxifen (Cat. No. 0999)

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Product Description
Product Specifications
Solubility
Preparing Stock Solutions
Calculators
Background References
Product Documents
Specific Notices

Key Product Details

Description

Metabolite of tamoxifen (Cat. No. 0999)

Alternative Names

4-OH-TAM,4OH-Tamoxifen

View all Estrogen and Related Receptor Modulators »

Product Description

(Z)-4-Hydroxytamoxifen is an estrogen receptor antagonist (IC₅₀ = 27 μM). (Z)-4-Hydroxytamoxifen is a Tamoxifen (Cat. No. 0999) metabolite exhibiting 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. Can be used in conditional gene knockout.

Product Specifications

Molecular Weight

387.51

Formula

C₂₆H₂₉NO₂

Storage

Store at +4°C

Purity

≥98% (HPLC)

Chemical Name

4-[(1Z)-1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]phenol

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.

Solubility

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	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 all affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	2.58 mL	12.90 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

Calculators

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Background References

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

Sula A tamoxifen receptor within a voltage-gated sodium channel. Mol.Cell. 2021 PMID: 33503406
Seeger Inhibition of human breast cancer cell proliferation with estradiol metabolites is as effective as with tamoxifen. Horm.Metab.Res. 2004 PMID: 15156405
Davis Small molecule-triggered Cas9 protein with improved genome-editing specificity. Nat.Chem.Biol. 2015 PMID: 25848930
Yu and Forman Simple and efficient production of (Z)-4-hydroxytamoxifen, a potent estrogen receptor modulator. J.Org.Chem. 2003 PMID: 14629178
Desta Comprehensive evaluation of tamox. sequential biotransformation by the human cytochrome P450 system in vitro: Prominent roles for CYP3A and CYP2D6. J.Pharm.Exp.Ther. 2004 PMID: 15159443
Jordan A monohydroxylated metabolite of tamox. with potent antioestrogenic activity. J.Endocrinology 1977 PMID: 591813