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SML1666

Sigma-Aldrich

4-Hydroxytamoxifen

≥98% (HPLC), solution, Tamoxifen metabolite

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
Pricing and availability is not currently available.

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

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

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This Item
H6278H7904SML1284
4-Hydroxytamoxifen Ready Made Solution 5 mg/mL in ethanol: isopropanol (95:5)

SML1666

4-Hydroxytamoxifen Ready Made Solution

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

H6278

4-Hydroxytamoxifen

(Z)-4-Hydroxytamoxifen ≥98% Z isomer

H7904

(Z)-4-Hydroxytamoxifen

Efavirenz Ready Made Solution 10 mg/mL in DMSO

SML1284

Efavirenz Ready Made Solution

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.

−20°C

shipped in

dry ice

shipped in

-

shipped in

-

shipped in

dry ice

biological source

synthetic

biological source

-

biological source

-

biological source

-

concentration

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

concentration

-

concentration

-

concentration

10 mg/mL in DMSO

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.

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

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    Certificates of Analysis (COA)

    Lot/Batch Number
    039M4123V
    11181115
    106M4037V
    11160804

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    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)
    Characterization of tamoxifen and 4-hydroxytamoxifen glucuronidation by human UGT1A4 variants.
    Sun D, et al.
    Breast Cancer Research, 8(4), R50-R50 (2006)
    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.
    Izumi Kaji et al.
    Gastroenterology, 159(4), 1390-1405 (2020-06-15)
    Myosin VB (MYO5B) is an essential trafficking protein for membrane recycling in gastrointestinal epithelial cells. The inactivating mutations of MYO5B cause the congenital diarrheal disease, microvillus inclusion disease (MVID). MYO5B deficiency in mice causes mislocalization of SGLT1 and NHE3, but
    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
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