94873

Supelco

4-Hydroxytamoxifen

(E) and (Z) isomers (50:50), analytical standard

Synonym(s):
4-(1-[4-(Dimethylaminoethoxy)phenyl]-2-phenyl-1-butenyl)phenol, cis/trans-4-Hydroxytamoxifen, 4-OHT
Empirical Formula (Hill Notation):
C26H29NO2
CAS Number:
Molecular Weight:
387.51
NACRES:
NA.24

Quality Level

grade

analytical standard

assay

≥97.5% (HPLC)

form

neat

shelf life

limited shelf life, expiry date on the label

application(s)

HPLC: suitable
gas chromatography (GC): suitable

impurities

≤5.0% water

Featured Industry

Forensics and Toxicology
Pharmaceutical (small molecule)

format

neat

SMILES string

CC\C(c1ccccc1)=C(/c2ccc(O)cc2)c3ccc(OCCN(C)C)cc3.CC\C(c4ccccc4)=C(\c5ccc(O)cc5)c6ccc(OCCN(C)C)cc6

InChI

1S/2C26H29NO2/c2*1-4-25(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/h2*5-17,28H,4,18-19H2,1-3H3/b26-25+;26-25-

InChI key

ZJLDABGSDWXVGE-BDSXMVAQSA-N

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General description

4-Hydroxytamoxifen is a first generation, selective estrogen receptor modulator (SERM) that functions as an antagonist in breast cancer cells but can display estrogen-like activities in the uterus and bone.

Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.
4-Hydroxytamoxifen may be used as a reference standard in the determination of 4-hydroxythmoxifen in plasma samples using high-performance liquid chromatography with fluorescence detection (HPLC).

Biochem/physiol Actions

Metabolite of the chemotherapeutic drug tamoxifen, exhibiting more potent estrogen agonist/antagonist activity than the parent drug. Also active as intra-membranous inhibitor of lipid peroxidation.

Pictograms

Exclamation markHealth hazard

Signal Word

Warning

Hazard Statements

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

4-Hydroxytamoxifen is an isoform-specific inhibitor of orphan estrogen-receptor-related (ERR) nuclear receptors beta and gamma.
Tremblay BG, et al.
Endocrinology, 142(10), 4572-4575 (2001)
Quantification of tamoxifen and three metabolites in plasma by high-performance liquid chromatography with fluorescence detection: application to a clinical trial.
Lee H-K, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 791(1-2), 245-253 (2003)
Takashi K Ito et al.
PloS one, 9(7), e102186-e102186 (2014-07-25)
Risk factors for atherosclerosis accelerate the senescence of vascular endothelial cells and promote atherogenesis by inducing vascular inflammation. A hallmark of endothelial senescence is the persistent up-regulation of pro-inflammatory genes. We identified CDC42 signaling as a mediator of chronic inflammation...
Rashmi Kumar et al.
Proceedings of the National Academy of Sciences of the United States of America, 112(5), E450-E457 (2015-01-23)
In mammals, VDJ recombination is responsible for the establishment of a highly diversified preimmune antibody repertoire. Acquisition of a functional Ig heavy (H) chain variable (V) gene rearrangement is thought to prevent further recombination at the IgH locus. Here, we...
Ziwei Li et al.
The EMBO journal, 34(6), 748-758 (2014-12-19)
PRMT5 is a type II protein arginine methyltransferase with roles in stem cell biology, reprograming, cancer and neurogenesis. During embryogenesis in the mouse, it was hypothesized that PRMT5 functions with the master germline determinant BLIMP1 to promote primordial germ cell...

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