4-[(1Z)-1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenol

• ChemBase ID: 132609
• Molecular Formular: C26H29NO2
• Molecular Mass: 387.51396
• Monoisotopic Mass: 387.21982917
• SMILES: CC/C(=C(\c1ccc(cc1)O)/c1ccc(cc1)OCCN(C)C)/c1ccccc1
• Canonical SMILES: CC/C(=C(\c1ccc(cc1)O)/c1ccc(cc1)OCCN(C)C)/c1ccccc1
• InChI: 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-
• InChIKey: TXUZVZSFRXZGTL-QPLCGJKRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1Z)-1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenol
• IUPAC Traditional name: 4-hydroxytamoxifen
• Synonyms: (Z)-4-OHT; (Z)-4-(1-[4-(Dimethylaminoethoxy)phenyl]-2-phenyl-1-butenyl)phenol; trans-4-Hydroxytamoxifen; (Z)-4-Hydroxytamoxifen; 4-[1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-phenyl-1-butenyl]phenol; (E/Z)-4-Hydroxytamoxifen; 4-Hydroxytamoxifen; 4-Hydroxy-(E/Z)-tamoxifen; Afimoxifene; TamoGel; (E/Z)-4-Hydroxy Tamoxifen; 4-[(1Z)-1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-phenyl-1-butenyl]phenol; (Z)-4-Hydroxytamoxifen; 4-Hydroxy-(Z)-tamoxifen; Hydroxytamoxifen; ICI 79280; (Z)-4-Hydroxy Tamoxifen

Database IDs

• CAS Number: 68392-35-8; 68047-06-3
• MDL Number: MFCD00278780
• PubChem SID: 24895814; 162226886
• PubChem CID: 449459

CALCULATED PROPERTIES

• Acid pKa: 9.451544
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.9840212
• LogD (pH = 7.4): 4.6672516
• Log P: 5.694083
• Molar Refractivity: 130.4117 cm^3
• Polarizability: 47.037178 Å^3
• Polar Surface Area: 32.7 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; ethanol: soluble20 mg/mL (with heating); Ethyl Acetate; Methanol; methanol: soluble10 mg/mL
• Apperance: Off-White Solid; Off-White to Pale Yellow Solid; powder
• Melting Point: 135-144°C; 142-145°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer; desiccated; protect from light; Refrigerator
• RTECS: SL1210000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63-20/21/22
• Safety Statements: 22-23-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332-H361
• GHS Precautionary statements: P280
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ESR1(2099), ESR2(2100), ESRRG(2104), IL6(3569)rat ... Ar(24208), Esr1(24890), Esr2(25149)

Product Information

• Purity: ≥98% (HPLC)
• Quality Level: PREMIUM

DETAILS

Sigma Aldrich - H7904

General description
4-Hydroxytamoxifen 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 selective estrogen receptor modulator (SERM).
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.

Toronto Research Chemicals - H954725

(Z)-4-Hydroxy Tamoxifen is a metabolite of Tamoxifen (T006000). (Z)-4-Hydroxy Tamoxifen is a hydroxylated analogue of Tamoxifen. (Z)-4-Hydroxy Tamoxifen is a metabolite of Tamoxifen with anti-estrogenic properties.

Toronto Research Chemicals - H954705

A selective estrogen receptor modulator.

REFERENCES

• Ruenitz, P.C. et al.: J. Med. Chem., 25, 1056 (1982)
• Ogura, K., et al.: Biochem. Pharmacol., 71, 1358 (1982)
• Oleson, L., et al.: J. Pharm. Pharmacol., 60, 1175 (1982)
• Levenson, A., et al.: Cancer Lett., 125, 215 (1998)
• Zhao, C., et al.: J. Steroid Biochem. Mol. Biol., 98, 1 (1998)
• Bellavance, E., et al.: J. Med. Chem., 52, 7488 (1998)