H7904

Sigma-Aldrich

(Z)-4-Hydroxytamoxifen

≥98% Z isomer

Synonym(s):
(Z)-4-(1-[4-(Dimethylaminoethoxy)phenyl]-2-phenyl-1-butenyl)phenol, (Z)-4-OHT, trans-4-Hydroxytamoxifen
Empirical Formula (Hill Notation):
C26H29NO2
CAS Number:
Molecular Weight:
387.51
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

powder

storage condition

desiccated
protect from light

solubility

methanol: 10 mg/mL
ethanol: 20 mg/mL (with heating)

Mode of action

enzyme | inhibits

antibiotic activity spectrum

neoplastics

originator

AstraZeneca

storage temp.

2-8°C

SMILES string

CC\C(c1ccccc1)=C(/c2ccc(O)cc2)c3ccc(OCCN(C)C)cc3

InChI

1S/C26H29NO2/c1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(28)15-11-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h5-17,28H,4,18-19H2,1-3H3/b26-25-

InChI key

TXUZVZSFRXZGTL-QPLCGJKRSA-N

Packaging

5, 25 mg in glass bottle

Biochem/physiol Actions

4-Hydroxytamoxifen (4-HT) is the active metabolite of tamoxifen which binds estrogen receptors (ER) and estrogen-related receptors (ERR) with estrogenic and anti-estrogenic effects. It is a cell permeable, selective estrogen receptor modulator (SERM). In Cas9 variants engineered with ligand-dependent inteins 4-Hydroxytamoxifen was used control Cas9 function, which reduced off target effects in CRISPR-mediated gene editing.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by AstraZeneca. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H7904.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Signal Word

Danger

hazcat

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1B - Repr. 1B

storage_class_code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Kevin M Davis et al.
Nature chemical biology, 11(5), 316-318 (2015-04-08)
Directly modulating the activity of genome-editing proteins has the potential to increase their specificity by reducing activity following target locus modification. We developed Cas9 nucleases that are activated by the presence of a cell-permeable small molecule by inserting an evolved...
Natalia L Kononenko et al.
Nature communications, 8, 14819-14819 (2017-04-08)
Autophagosomes primarily mediate turnover of cytoplasmic proteins or organelles to provide nutrients and eliminate damaged proteins. In neurons, autophagosomes form in distal axons and are trafficked retrogradely to fuse with lysosomes in the soma. Although defective neuronal autophagy is associated...
Pei-Shan Hou et al.
Nature communications, 10(1), 3581-3581 (2019-08-10)
The bimodal requisite for a genetic program and external stimuli is a key feature of sensory circuit formation. However, the contribution of cell-intrinsic codes to directing sensory-specific circuits remains unknown. Here, we identify the earliest molecular program that preselects projection...
Marcus Conrad et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(36), 15774-15779 (2010-08-28)
Protein tyrosine phosphatases (PTPs) are regulated through reversible oxidation of the active-site cysteine. Previous studies have implied soluble reactive oxygen species (ROS), like H(2)O(2), as the mediators of PTP oxidation. The potential role(s) of peroxidized lipids in PTP oxidation have...
Emily R Moore et al.
Stem cell research & therapy, 9(1), 190-190 (2018-07-13)
The fully developed adult skeleton adapts to mechanical forces by generating more bone, usually at the periosteal surface. Progenitor cells in the periosteum are believed to differentiate into bone-forming osteoblasts that contribute to load-induced adult bone formation, but in vivo evidence...
Articles
The CRISPR-Cas9 system is an RNA-guided genome-editing tool that provides researchers a simple, easy, and quick way to modify the genomes of various organisms.
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