97151-02-5

Basic information

• Product Name: a-Hydroxy Tamoxifen
• Synonyms: (E)-α-Hydroxy Tamoxifen
• CAS NO: 97151-02-5
• Molecular Formula: C₂₆H₂₉NO₂
• Molecular Weight: 387.52
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Amines;Aromatics
• Mol File: 97151-02-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 115-119°C
• Boiling Point: 533.8°Cat760mmHg
• Flash Point: 276.6°C
• Appearance: /
• Density: 1.094g/cm³
• Vapor Pressure: 3.17E-12mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: Amber Vial, -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.13±0.20(Predicted)
• CAS DataBase Reference: a-Hydroxy Tamoxifen(CAS DataBase Reference)
• NIST Chemistry Reference: a-Hydroxy Tamoxifen(97151-02-5)
• EPA Substance Registry System: a-Hydroxy Tamoxifen(97151-02-5)

Safety Data

• Hazardous Substances Data: 97151-02-5(Hazardous Substances Data)

Usage

Description

α-Hydroxy Tamoxifen is a metabolite of the chemotherapeutic drug tamoxifen, which is a selective estrogen receptor (ER) modulator widely used in the therapeutic and chemopreventive treatment of breast cancer. It exhibits a more potent estrogen agonist/antagonist activity than the parent drug and is also active as an intramembranous inhibitor of lipid peroxidation. α-Hydroxy Tamoxifen is a reactive metabolite formed by the action of cytochrome P450 3A4 in human liver and can be further converted into genotoxic DNA adducts. It is a pale yellow solid.

Uses

Used in Pharmaceutical Industry:
α-Hydroxy Tamoxifen is used as a chemotherapeutic agent for the treatment of breast cancer due to its potent estrogen agonist/antagonist activity. It modulates the action of estrogen receptors in different tissues, acting as an antagonist in breast tissue, an agonist in bone and blood vessels, and a partial agonist in uterine tissues.
Used in Anticancer Research:
α-Hydroxy Tamoxifen is used as a research compound to study its role in the development of hepatocarcinoma in rats through its conversion into genotoxic DNA adducts via a mechanism involving reversible O-sulfonation of the hydroxyl moiety.
Used in Drug Metabolism Studies:
α-Hydroxy Tamoxifen is used as a model compound in drug metabolism studies to understand the formation and effects of reactive metabolites formed by the action of cytochrome P450 3A4 in human liver.

InChI:InChI=1/C26H29NO2/c1-20(28)25(21-10-6-4-7-11-21)26(22-12-8-5-9-13-22)23-14-16-24(17-15-23)29-19-18-27(2)3/h4-17,20,28H,18-19H2,1-3H3/b26-25-

Upstream product

• 19118-19-5 trans-(E)-1-bromo-2-<4-<2-(dimethylamino)ethoxy>phenyl>-1,2-diphenylethene 
• 75-07-0 acetaldehyde 
• 205924-33-0 trans-α-acetoxytamoxifen 
• 556834-76-5 (E,Z)-4-[4-(2-dimethylaminoethoxy)phenyl]-3,4-diphenyl-but-3-en-2-one 

Downstream Products

• 288617-57-2 (E)-4-{4-[2-(N-Ethoxycarbonyl-N-methylamino)ethoxy]phenyl}-3,4-diphenyl-3-buten-2-ol 
• 404574-00-1 2-[2-{(E)-4-(4-(2-dimethylaminoethoxy)phenyl)-3,4-diphenyl-but-3-enyl}]isoindole-1,3-dione 
• 404574-02-3 [2-{(E)-4-(4-(2-dimethylaminoethoxy)phenyl)-3,4-diphenyl but-3-enyl}]amine 
• 162070-61-3 alpha-Hydroxy-N-desmethyltamoxifen 
• 288617-60-7 (E)-2-Acetoxy-4-{4-[2-(methylamino)ethoxy]phenyl}-3,4-diphenyl-3-butene 
• 288617-58-3 (E)-4-{4-[2-(N-Benzyloxycarbonyl-N-methylamino)ethoxy]phenyl}-3,4-diphenyl-3-buten-2-ol 
• 288617-59-4 (E)-2-Acetoxy-4-{4-[2-(N-benzyloxycarbonyl-N-methylamino)ethoxy]phenyl}-3,4-diphenyl-3-butene 

Relevant articles and documents

Photoredox-Catalyzed C-H Arylation of Internal Alkenes to Tetrasubstituted Alkenes: Synthesis of Tamoxifen

Visible-light-induced direct C-H arylation of S,S-functionalized internal alkenes, that is, α-oxo ketene dithioacetals and analogues, has been efficiently realized with aryldiazonium salts (ArN2BF4) as coupling partners and Ru(bpy)s

Hydroxy derivatives of tamoxifen

In the exploration of the structural features that affect the RBA (binding affinity for the estrogen receptor of rat uterus relative to that of estradiol) in the tamoxifen [trans-(Z)-1-[4-(dimethylamino)ethoxy]-1,2-diphenyl-1-butene] series, several derivatives variously substituted in the 1-phenyl group have been synthesized. In the tamoxifen series, the descriptors E and Z, which define the configuration of the geometrical isomers and depend on the location and nature of substituents in the aromatic moieties and the ethyl group, may vary, although the relative configuration (cis or trans) does not. In order to avoid confusion the terms cis and trans will be used in this paper to refer to the relative positions of the 4-[2-(dimethylamino)ethoxy]phenyl and ethyl (or hydroxyethyl, hydroxypropyl, or bromo) substituents attached to the ethene moiety]. The final stage of each synthesis involved acid-catalyzed dehydration of a tertiary alcohol, and, in contrast to the known 3- and 4-hydroxy derivatives which were obtained as near-equimolar cis,trans mixtures, only the trans forms of the 2-hydroxy, 2-methyl, 2,4-dihydroxy, and 4-hydroxy-2-methyl derivatives were obtained. Also, in contrast to the trans forms of the 3- and 4-hydroxy derivatives, which are readily equilibrated to cis,trans mixtures, the trans 2-hydroxy derivative could not be isomerized. Tamoxifen and 2-methyltamoxifen had similar RBA's (~1% of that of E2), but that of 2-hydroxytamoxifen was much lower (0.1%). Introduction of a second hydroxyl group (2,4-dihydroxy derivative) enhanced the RBA, and for the 4-hydroxy-2-methyl derivative, the RBA and growth inhibitory activity against the MCF-7 mammary tumor cell line in vitro were high and comparable to those of 4-hydroxytamoxifen, a metabolite of the parent drug. Tamoxifen derivatives hydroxylated at positions 3 or 4 of the 1-butene moiety and the 5-hydroxy-1-pentene analogue were also synthesized, but they had very low RBA values.