T176

4-Hydroxytamoxifen

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

• Synonym(s): 4-(1-[4-(Dimethylaminoethoxy)phenyl]-2-phenyl-1-butenyl)phenol, 4-OHT, cis/trans-4-Hydroxytamoxifen
• Empirical Formula (Hill Notation): C₂₆H₂₉NO₂
• CAS Number: 68392-35-8
• Molecular Weight: 387.51
• UNSPSC Code: 41116107
• PubChem Substance ID: 24899989
• NACRES: NA.24

Properties

• grade: analytical standard
• Quality Level: 200
• form: powder
• technique(s): HPLC: suitable; gas chromatography (GC): suitable
• solubility: ethanol: 20 mg/mL
• antibiotic activity spectrum: neoplastics
• application(s): forensics and toxicology; pharmaceutical (small molecule)
• format: neat
• Mode of action: enzyme | inhibits
• 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
• Gene Information: human ... ESR1(2099) , ESR2(2100) , ESRRG(2104) , IL6(3569) ; rat ... Ar(24208) , Esr1(24890) , Esr2(25149)

Description

General description

4-Hydroxytamoxifen is an antiestrogenic agent and one of the active metabolites of tamoxifen, formed upon its hydroxylation cytochrome P4502D6 (CYP2D6). Tamoxifen is used significantly in breast cancer as hormonal therapy.

Application

The 4-Hydroxytamoxifen analytical standard can be used as follows:

• Determination of tamoxifen and its three metabolites from dried blood spot (DBS) discs by ultra-high performance liquid chromatography-electrospray ionization-tandem mass spectrometry (UHPLC-ESI-MS/MS)
• Simultaneous estimation of tamoxifen, 4-hydroxytamoxifen, and endoxifen from DBS samples by UHPLC-MS/MS
• Development and validation of a non-aqueous capillary electrophoretic (NACE) method coupled with capacitively coupled contactless conductivity detection (C⁴D) to analyze tamoxifen and its three main metabolites after their liquid-liquid extraction (LLE) from human plasma samples obtained from breast cancer patients
• Multi-residue analysis of human plasma samples to quantify tamoxifen and its degradation products using the non-aqueous capillary electrophoretic (NACE) method combined with UV-detection
• Combined detection of tamoxifen and centchroman, along with their degradation products in human plasma samples by LC-ESI-MS/MS

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.

Other Notes

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Safety Information

• Pictograms: GHS08,GHS07
• Signal Word: Warning
• Hazard Statements: H302 + H312 + H332,H315,H319,H361fd
• Precautionary Statements: P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves