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H6278

Sigma-Aldrich

4-Hydroxytamoxifen

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

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Synonym(s):
4-(1-[4-(Dimethylaminoethoxy)phenyl]-2-phenyl-1-butenyl)phenol, 4-OHT, cis/trans-4-Hydroxytamoxifen
Empirical Formula (Hill Notation):
C26H29NO2
CAS Number:
Molecular Weight:
387.51
PubChem Substance ID:

Quality Level

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

SMILES string

CC\C(c1ccccc1)=C(/c2ccc(O)cc2)c3ccc(OCCN(C)C)cc3.CC\C(c4ccccc4)=C(\c5ccc(O)cc5)c6ccc(OCCN(C)C)cc6

InChI

1S/2C26H29NO2/c2*1-4-25(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/h2*5-17,28H,4,18-19H2,1-3H3/b26-25+;26-25-

InChI key

ZJLDABGSDWXVGE-BDSXMVAQSA-N

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This Item
SML1666T176H7904
4-Hydroxytamoxifen ≥70% Z isomer (remainder primarily E-isomer)

Sigma-Aldrich

H6278

4-Hydroxytamoxifen

4-Hydroxytamoxifen analytical standard, (E) and (Z) isomers (50:50)

Supelco

T176

4-Hydroxytamoxifen

(Z)-4-Hydroxytamoxifen ≥98% Z isomer

Sigma-Aldrich

H7904

(Z)-4-Hydroxytamoxifen

form

powder

form

solution

form

powder

form

powder

storage condition

desiccated, protect from light

storage condition

-

storage condition

-

storage condition

desiccated, protect from light

solubility

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

solubility

-

solubility

ethanol: 20 mg/mL

solubility

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

originator

AstraZeneca

originator

-

originator

-

originator

AstraZeneca

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

-

storage temp.

2-8°C

Application

4-Hydroxytamoxifen has been used:
  • to induce the recombination of small intestinal organoids.
  • to study its impact on the ability of human peripheral blood mononuclear cells (PMNCs) to form hematopoietic colonies.
  • to induce overexpression of MYCN in the neuroblastoma cell line to determine how the elevated MYCN expression influences the sensitivity of neuroblastoma cells to BIRC5/survivin inhibitor, YM155-induced apoptosis.

Biochem/physiol Actions

Metabolite of the chemotherapeutic drug tamoxifen, exhibiting more potent estrogen agonist/antagonist activity than the parent drug. Also active as intra-membranous inhibitor of lipid peroxidation.

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.

Pictograms

Exclamation markHealth hazard

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Product Number
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25G
Pack Size/Quantity

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705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

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Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

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  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

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Tamoxifen for the treatment of myeloproliferative neoplasms: A Phase II clinical trial and exploratory analysis
Fang Z, et al.
Nature Communications, 14(1), 7725-7725 (2023)
YM155 inhibits neuroblastoma growth through degradation of MYCN: A new role as a USP7 inhibitor
Li X, et al.
Journal of Separation Science, 181, 106343-106343 (2023)
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In development of colorectal cancer, mutations in APC are often followed by mutations in oncogene KRAS The latter changes cellular metabolism and is associated with the Warburg phenomenon. Glucose-regulated protein 78 (Grp78) is an important regulator of the protein-folding machinery
Matthew Bechard et al.
Molecular and cellular biology, 29(8), 2092-2104 (2009-02-19)
Phosphatidylinositol 3-kinase (PI3K), protein kinase B (AKT1), and c-myc have well-established roles in promoting the maintenance of murine embryonic stem cells (mESCs). In contrast, the activity of glycogen synthase kinase 3beta (GSK3beta), a negatively regulated target of AKT1 signaling, antagonizes
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Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research, 34(8), 1387-1392 (2019-03-20)
The growth plate provides a substantial source of mesenchymal cells in the endosteal marrow space during endochondral ossification. The current model postulates that a group of chondrocytes in the hypertrophic zone can escape from apoptosis and transform into cells that

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