SML1666

4-Hydroxytamoxifen

≥98% (HPLC), solution, Estrogen receptor antagonist

• Synonym(s): 4-OHT, cis/trans-4-Hydroxytamoxifen
• Empirical Formula (Hill Notation): C₂₆H₂₉NO₂
• CAS Number: 68392-35-8
• Molecular Weight: 387.51
• UNSPSC Code: 12352200
• NACRES: NA.77
• Form: solution

Properties

• Product Name: 4-Hydroxytamoxifen Ready Made Solution, 5 mg/mL in ethanol: isopropanol (95:5)
• biological source: synthetic
• Quality Segment: 200
• form: solution
• concentration: 5 mg/mL in ethanol: isopropanol (95:5)
• shipped in: dry ice
• storage temp.: −20°C
• SMILES string: N(CCOc1ccc(cc1)\C(=C(\CC)/c3ccccc3)\c2ccc(cc2)O)(C)C
• 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

Description

Biochem/physiol Actions

4-Hydroxytamoxifen is an active metabolite of Tamoxifen.

4-Hydroxytamoxifen is an active metabolite of Tamoxifen. 4-Hydroxytamoxifen is formed by cytochrome P450 2D6 in human liver and is a potent and selective estrogen receptor antagonist. 4-Hydroxytamoxifen has been used to stimulate LC3 lipidation and to form autophagic vesicles in a superoxide-dependent manner. Tamoxifen and 4-Hydroxytamoxifen markedly induce cytochrome P450 3A4 (a major drug-metabolizing enzyme) in primary cultures of human hepatocytes. 4-Hydroxytamoxifen undergoes a cis-trans (E-Z) isomerization, a process that occurs in all common laboratory solvents.

Trans isoform of 4-hydroxytamoxifen possesses antiestrogenic activity, while the cis 4-hydroxytamoxifen serves as a key agonist for estrogen receptor. 4-Hydroxytamoxifen promotes apoptosis via activation of p38 pathway in breast cancer cell cultures.

Preparation Note

4-Hydroxytamoxifen is provided in a 13 mM solution. The recommended working concentration is 10-100 μM. Therefore, 4-Hydroxytamoxifen Ready Made Solution should be diluted 1:130 - 1:1,300 in cell culture media.

Disclaimer

Supply conditions do not apply to the regions and states of Brazil: North, Northeast, Mato Grosso do Sul, Mato Grosso, and Rio Grande do Sul.

Safety Information

• Pictograms: GHS02,GHS08,GHS07
• Signal Word: Danger
• Hazard Codes: H225,H319,H350,H360FD,H412
• Precautionary Statements: P202 - P210 - P233 - P273 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Aquatic Chronic 3 - Carc. 1B - Eye Irrit. 2 - Flam. Liq. 2 - Repr. 1B
• Storage Class: 3 - Flammable liquids
• WGK: WGK 3
• Flash Point (°F): 55.4 °F
• Flash Point (°C): 13 °C