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SML1666

4-Hydroxytamoxifen

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

Synonym(s):

4-OHT, cis/trans-4-Hydroxytamoxifen

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About This Item

Empirical Formula (Hill Notation):
C26H29NO2
CAS Number:
68392-35-8
Molecular Weight:
387.51
UNSPSC Code:
12352200
NACRES:
NA.77
Form:
solution
Quality level:
200

Key Documents

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Product Name

4-Hydroxytamoxifen Ready Made Solution, 5 mg/mL in ethanol: isopropanol (95:5)

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

biological source

synthetic

form

solution

concentration

5 mg/mL in ethanol: isopropanol (95:5)

shipped in

dry ice

storage temp.

−20°C

Quality Level

200

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1 of 4

This Item
H6278H7904579002
4-Hydroxytamoxifen Ready Made Solution 5 mg/mL in ethanol: isopropanol (95:5)

Sigma-Aldrich

SML1666

4-Hydroxytamoxifen Ready Made Solution

4-Hydroxytamoxifen ≥70% Z isomer (remainder primarily E-isomer)

Sigma-Aldrich

H6278

4-Hydroxytamoxifen

(Z)-4-Hydroxytamoxifen ≥98% Z isomer

Sigma-Aldrich

H7904

(Z)-4-Hydroxytamoxifen

Tamoxifen, 4-Hydroxy-, (Z)- 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.

Sigma-Aldrich

579002

Tamoxifen, 4-Hydroxy-, (Z)-

form

solution

form

powder

form

powder

form

solid

Quality Level

200

Quality Level

300

Quality Level

300

Quality Level

200

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

shipped in

dry ice

shipped in

-

shipped in

-

shipped in

ambient

biological source

synthetic

biological source

-

biological source

-

biological source

-

concentration

5 mg/mL in ethanol: isopropanol (95:5)

concentration

-

concentration

-

concentration

-

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.[1] 4-Hydroxytamoxifen promotes apoptosis via activation of p38 pathway in breast cancer cell cultures.[2]

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.

signalword

Danger

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000508236
0000508236
0000479054
0000445771
0000445771

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Characterization of tamoxifen and 4-hydroxytamoxifen glucuronidation by human UGT1A4 variants.
Sun D, et al.
Breast Cancer Research, 8(4), R50-R50 (2006)
Activation of the p38 mitogen-activated protein kinase pathway by estrogen or by 4-hydroxytamoxifen is coupled to estrogen receptor-induced apoptosis.
Zhang C C and Shapiro D J
The Journal of Biological Chemistry, 275(1), 479-486 (2000)
Chao Wang et al.
Nature communications, 13(1), 1969-1969 (2022-04-14)
Activation of microglia is a prominent pathological feature in tauopathies, including Alzheimer's disease. How microglia activation contributes to tau toxicity remains largely unknown. Here we show that nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) signaling, activated by tau, drives
Jinming Zhao et al.
iScience, 24(12), 103425-103425 (2021-12-09)
We previously showed stabilization of NIK-induced activation of NF-κB non-canonical signaling suppresses MLL-AF9-induced AML. In the current study, we demonstrate that deletion of NF-κB non-canonical RelB prevents the inhibitory effect of NIK stabilization in MLL-AF9 AML. Mechanistically, RelB suppresses its
Izumi Kaji et al.
JCI insight, 6(16) (2021-07-02)
Functional loss of myosin Vb (MYO5B) induces a variety of deficits in intestinal epithelial cell function and causes a congenital diarrheal disorder, microvillus inclusion disease (MVID). The impact of MYO5B loss on differentiated cell lineage choice has not been investigated.
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