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H7904

Sigma-Aldrich

(Z)-4-Hydroxytamoxifen

≥98% (HPLC), powder, estrogen receptor modulator

Synonym(s):

4OH-Tamoxifen, (Z)-4-(1-[4-(Dimethylaminoethoxy)phenyl]-2-phenyl-1-butenyl)phenol, (Z)-4-OHT, trans-4-Hydroxytamoxifen

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About This Item

Empirical Formula (Hill Notation):
C26H29NO2
CAS Number:
68047-06-3
Molecular Weight:
387.51
MDL number:
MFCD00278780
UNSPSC Code:
51111800
PubChem Substance ID:
24895814
NACRES:
NA.77
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Product Name

(Z)-4-Hydroxytamoxifen, ≥98% Z isomer

Quality Level

300

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated
protect from light

solubility

methanol: 10 mg/mL
ethanol: 20 mg/mL (with heating)

antibiotic activity spectrum

neoplastics

Mode of action

enzyme | inhibits

originator

AstraZeneca

storage temp.

2-8°C

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Show Differences

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H6278579002E8284
(Z)-4-羟三苯氧胺 ≥98% Z isomer

H7904

(Z)-4-羟三苯氧胺

4-羟基他莫西芬 ≥70% Z isomer (remainder primarily E-isomer)

H6278

4-羟基他莫西芬

(Z)-4-羟基-三苯氧胺，大包装 A cell-permeable, active metabolite of Tamoxifen that acts as a potent inhibitor of PKC. It is more potent than the parent compound and inhibits PKC by modifying its catalytic domain.

579002

(Z)-4-羟基-三苯氧胺，大包装

(E/Z)-盐酸内多昔芬水合物 ≥98% (HPLC)

E8284

(E/Z)-盐酸内多昔芬水合物

form

powder

form

powder

form

solid

form

solid

Quality Level

300

Quality Level

300

Quality Level

200

Quality Level

100

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage condition

desiccated, protect from light

storage condition

desiccated, protect from light

storage condition

OK to freeze

storage condition

desiccated

solubility

ethanol: 20 mg/mL (with heating), methanol: 10 mg/mL

solubility

methanol: 10 mg/mL, ethanol: 20 mg/mL (with heating)

solubility

methanol: 10 mg/mL, ethanol: 20 mg/mL (heating may be required)

solubility

DMSO: >10 mg/mL

General description

4-Hydroxytamoxifen (4-OHT) is a metabolite of the antiestrogen tamoxifen in humans and other mammals.[1] Both the Z (trans) and E (cis) 4-OHT isomers exhibit antiestrogenic properties in immature rats. Studies on the structure-function relationships of fixed ring systems have revealed that the trans isomer is a potent antiestrogen, while the cis isomer is relatively weaker (about 100 times less potent) as an antiestrogen in T47D breast cancer cells in vitro. 4-OHT binds to estrogen receptors (ER) and estrogen-related receptors (ERR), exerting both estrogenic and anti-estrogenic effects. This compound is a cell-permeable, selective estrogen receptor modulator (SERM). Compared to tamoxifen and its other metabolites, 4-OHT demonstrates a higher affinity for binding to estrogen receptors, resulting in 50 to 100-fold greater potency in inhibiting cell proliferation in normal human breast cells and breast cancer cell lines in culture.[2] Moreover, 4-OHT has been found effective in inhibiting the growth of these cells in the absence of estrogen when cell proliferation was induced by insulin or epidermal growth factor.

Application

(Z)-4-Hydroxytamoxifen has been used:
  • as a media supplement to study the cell viability by WST-1 Assay[3]
  • for inducing deletion of transforming growth factor-β (TGF-β gene in mice[4]
  • to induce Cre recombinase activity in vitro.[5]

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by AstraZeneca. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Signal Word

Danger

Hazard Statements

H302,H350,H360FD,H410

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1B - Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves
  • Specification Sheet

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    Certificates of Analysis (COA)

    Lot/Batch Number
    0000280566
    0000280566
    0000420481
    0000367381
    0000280565

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    Tamoxifen and hydroxytamoxifen as intramembraneous inhibitors of lipid peroxidation. Evidence for peroxyl radical scavenging activity
    Cust'odio JBA, et al.
    Biochemical Pharmacology, 47, 1989-1998 (1994)
    Keratinocyte-derived TGF? is not required to maintain skin immune homeostasis
    Yang Y, et al.
    Journal of Dermatological Science, 94(2), 290-297 (2019)
    Formulation of anti-miR-21 and 4-hydroxytamoxifen co-loaded biodegradable polymer nanoparticles and their antiproliferative effect on breast cancer cells
    Devulapally R, et al.
    J. Mol. Pharmacol., 12, 2080-2092 (2015)
    Microglia-Specific Expression of Olfml3 Is Directly Regulated by Transforming Growth Factor ?1-Induced Smad2 Signaling
    Neidert N, et al.
    Frontiers in Immunology, 9, 1728-1728 (2018)
    Decreased expression of Yes-associated protein is associated with outcome in the luminal A breast cancer subgroup and with an impaired tamoxifen response
    Lehn S, et al.
    BMC Cancer, 14, 119-119 (2014)
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