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4-HYDROXYTAMOXIFEN

CAS No.
68047-06-3
Chemical Name:
4-HYDROXYTAMOXIFEN
Synonyms
hydroxytamoxifen;4-OHT;C05011;(Z)-4-OHT;ici79,280;(E)-4’4-Benzyloxy β4-HYDROXYTAMOXIFEN;TAMOXIFEN, 4-HYDROXY-;cis-4-Hydroxytamoxifen
CBNumber:
CB0754622
Molecular Formula:
C26H29NO2
Molecular Weight:
387.51
MDL Number:
MFCD00468090
MOL File:
68047-06-3.mol
MSDS File:
SDS
Last updated:2023-06-30 15:45:59

4-HYDROXYTAMOXIFEN Properties

Melting point 105-107°C
Boiling point 513.45°C (rough estimate)
Density 1.1005 (rough estimate)
refractive index 1.6000 (estimate)
storage temp. 2-8°C
solubility 95% ethanol: 20 mg/mL
pka 10.35±0.15(Predicted)
form powder
color white
Stability Stable. Store cool. Incompatible with strong oxidizing agents.
InChIKey TXUZVZSFRXZGTL-OCEACIFDSA-N
CAS DataBase Reference 68047-06-3
NCI Dictionary of Cancer Terms 4-hydroxytamoxifen
FDA UNII 95K54647BZ

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08,GHS09
Signal word  Danger
Hazard statements  H302-H350-H360FD-H410
Precautionary statements  P201-P202-P264-P273-P301+P312-P308+P313
Hazard Codes  Xn
Risk Statements  20/21/22-63
Safety Statements  22-23-36
WGK Germany  3
RTECS  SL1210000
NFPA 704
0
3 0

4-HYDROXYTAMOXIFEN price More Price(28)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich H7904 (Z)-4-Hydroxytamoxifen ≥98% Z isomer 68047-06-3 5mg $183 2024-03-01 Buy
Sigma-Aldrich 5.08225 InSolution Tamoxifen, 4-Hydroxy-, ( Z)- - CAS 68047-06-3 - Calbiochem 68047-06-3 2mg $96.7 2024-03-01 Buy
Sigma-Aldrich 579002 Tamoxifen, 4-Hydroxy-, (Z)- 68047-06-3 5mg $223 2023-01-07 Buy
Cayman Chemical 14854 (Z)-4-hydroxy Tamoxifen ≥98% 68047-06-3 1mg $37 2024-03-01 Buy
Cayman Chemical 14854 (Z)-4-hydroxy Tamoxifen ≥98% 68047-06-3 5mg $134 2024-03-01 Buy
Product number Packaging Price Buy
H7904 5mg $183 Buy
5.08225 2mg $96.7 Buy
579002 5mg $223 Buy
14854 1mg $37 Buy
14854 5mg $134 Buy

4-HYDROXYTAMOXIFEN Chemical Properties,Uses,Production

Chemical Properties

Powder

Uses

tamoxifen metabolite, anti-estrogen, see Tamoxifen 1,01038

Uses

A metabolite of Tamoxifen (T006000). A hydroxylated analogue of Tamoxifen with anti-estrogenic properties.

Uses

(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.

Uses

A hydroxylated analogue of tamoxifen with anti-estrogenic properties. A metabolite of Tamoxifen.

Definition

ChEBI: Afimoxifene is a tertiary amino compound that is tamoxifen in which the phenyl group which is in a Z- relationship to the ethyl substituent is hydroxylated at the para- position. It is the active metabolite of tamoxifen. It has a role as an antineoplastic agent, an estrogen receptor antagonist and a metabolite. It is a tertiary amino compound and a member of phenols. It is functionally related to a tamoxifen.

General Description

A cell-permeable, active metabolite of Tamoxifen (Cat. No. 579000) that acts as a potent inhibitor of PKC. It is more potent than the parent compound and inhibits PKC by modifying its catalytic domain. Also available as a 10 mM solution in EtOH (Cat. No. 508225).

Biological Activity

estrogen receptors (er) are members of the superfamily of ligand-modulated nuclear receptors that mediate the actions of steroid hormones, vitamin d, retinoids, and thyroid hormones. er is activated in vivo when bound by naturally occurring estrogens such as 17α-estradiol. in addition to regulating these physiological processes, estrogen also plays a central role in stimulating breast cancer growth. (z)-tamoxifen is a first generation selective er modulators that is currently approved by the fda and is widely used to treat estrogen-dependent breast cancers. its active metabolite, (z)-4-hydroxytamoxifen, is a potent estrogen receptor modulator.

Biochem/physiol Actions

Cell permeable: yes

in vitro

(z)-4-hydroxytamoxifen binds to er with 8-fold higher affinity than tamoxifen. it was found that only the z isomer has the required antiestrogenic activity; the (e)-4-hydroxytamoxifen has only about 5% of its affinity for the er [1].

in vivo

the antioestrogenic activities of (z)-4-hydroxytamoxifen and tamoxifen were determined after oral administration. (z)-4-hydroxytamoxifen was administered to groups of immature rats which also received s.c. injections of 0-2 μg oestradiol. both compounds produced a dose-related decrease in uterine wet weight when compared with the oestradiol-treated controls. at a dose of 1 μg/day, the antiuterotrophic effects of (z)-4-hydroxytamoxifen and tamoxifen were not significantly different but at 5μg/day, (z)-4-hydroxytamoxifen was more active (p < 0.01). (z)-4-hydroxytamoxifen therefore appears to retain its potent antioestrogenic activity after oral administration [2].

storage

-20°C

References

[1] donna d. yu and barry m. forman. simple and efficient production of (z)-4-hydroxytamoxifen, a potent estrogen receptor modulator. j. org. chem. 2003, 68, 9489-9491
[2] jordan vc, collins mm, rowsby l, prestwich g. a monohydroxylated metabolite of tamoxifen with potent antioestrogenic activity. j endocrinol. 1977 nov;75(2):305-16.

611-99-4
68047-06-3
Synthesis of 4-HYDROXYTAMOXIFEN from 4,4'-Dihydroxybenzophenone
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View Lastest Price from 4-HYDROXYTAMOXIFEN manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
4-HYDROXYTAMOXIFEN pictures 2021-07-02 4-HYDROXYTAMOXIFEN
68047-06-3
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
4-HYDROXYTAMOXIFEN USP/EP/BP pictures 2021-06-25 4-HYDROXYTAMOXIFEN USP/EP/BP
68047-06-3
US $1.10 / g 1g 99.9% 100 Tons Min Dideu Industries Group Limited
(Z)-4-Hydroxy TaMoxifen  pictures 2020-05-10 (Z)-4-Hydroxy TaMoxifen
68047-06-3
US $1.00 / KG 1KG 99% 20T Shaanxi Dideu Medichem Co. Ltd
  • 4-HYDROXYTAMOXIFEN pictures
  • 4-HYDROXYTAMOXIFEN
    68047-06-3
  • US $15.00-10.00 / KG
  • 99%+ HPLC
  • Zhuozhou Wenxi import and Export Co., Ltd

4-HYDROXYTAMOXIFEN Spectrum

trans-4-Hydroxytamoxifen, (Z)-4-(1-[4-(Dimethylaminoethoxy)phenyl]-2-phenyl-1-butenyl)phenol (Z)-3,4-Diphenyl-4-[4-[2-(dimethylamino)ethoxy]phenyl]-3-buten-1-ol 2-[4-[(E)-1-(4-Hydroxyphenyl)-2-phenyl-1-butenyl]phenoxy]-N,N-dimethylethanamine 4-[(E)-1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-phenyl-1-butenyl]phenol cis-4-Hydroxytamoxifen N,N-Dimethyl-2-[4-[(E)-1-(4-hydroxyphenyl)-2-phenyl-1-butenyl]phenoxy]ethanamine TAMOXIFEN 4-HYDROXY, (E) AND (Z) ISOMERS (50:50) (Z)-4-(1-[4-(Dimethylaminoethoxy)phenyl]-2-phenyl-1-butenyl)phenol C05011 4-OHT See H9711, H9712, or H9716 4-(1-(4-(dimethylaminoethoxy)phenyl)-2-phenyl-1-butenyl)phenol (Z)-4-OHT 4-HYDROXYTAMOXIFEN TAMOXIFEN, 4-HYDROXY- ici79,280 trans-4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenyl-1-butenyl)phenol (E)-4&rsquo 4-[(1Z)-1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]phenol Tamoxifen, 4-Hydroxy-, (Z)- - CAS 68047-06-3 - Calbiochem 4-Benzyloxy &beta Phenol, 4-[(1Z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]- Tamoxifen Citrate Impurity 9(4-Hydroxy Tamoxifen) 4-HYDROXYTAMOXIFEN USP/EP/BP hydroxytamoxifen trans-4-Hydroxytamoxifen inhibit,Estrogen Receptor/ERR,4-Hydroxytamoxifen,estrogen receptor,oral,CRISPR/Cas9,4Hydroxytamoxifen,Inhibitor,(Z)-Afimoxifene,nucleus translocation,4 Hydroxytamoxifen Tamoxifen Citrate Impurity 12 68047-06-3 C26H29NO2 BioChemical Antibiotics Antibiotics A to Z Antibiotics G-M Aromatics Metabolites & Impurities Drug Analogues Intermediates & Fine Chemicals Pharmaceuticals Steroids