Skip to Content
Merck
All Photos(1)

Documents

SML1666

Sigma-Aldrich

4-Hydroxytamoxifen

≥98% (HPLC), solution, Tamoxifen metabolite

Synonym(s):

4-OHT, cis/trans-4-Hydroxytamoxifen

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

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

product name

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

biological source

synthetic

Quality Level

200

form

solution

concentration

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

shipped in

dry ice

storage temp.

−20°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

Biochem/physiol Actions

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

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.

Signal Word

Danger

Hazard Classifications

Aquatic Chronic 3 - Carc. 1B - Eye Irrit. 2 - Flam. Liq. 2 - Repr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

55.4 °F

Flash Point(C)

13 °C

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 4

1 of 4

Tamoxifen citrate United States Pharmacopeia (USP) Reference Standard

USP

1643306

Tamoxifen citrate

Tamoxifen analytical standard

Supelco

85256

Tamoxifen

Fulvestrant >98% (HPLC)

Sigma-Aldrich

I4409

Fulvestrant

Bexarotene ≥98% (HPLC)

Sigma-Aldrich

SML0282

Bexarotene

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)
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.
Kindlin-2 preserves integrity of the articular cartilage to protect against osteoarthritis.
Wu, et al.
Nature aging, 2, 332-347 (2023)
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service