Skip to Content
MilliporeSigma

Key Documents

View All Documentation

Skip To

H6278

4-Hydroxytamoxifen

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

1 of 1 reviewers took part in a promotion

Synonym(s):

4-(1-[4-(Dimethylaminoethoxy)phenyl]-2-phenyl-1-butenyl)phenol, 4-OHT, cis/trans-4-Hydroxytamoxifen

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View
Size/SKUAvailabilityPrice
10 mg

Available to ship TODAYfromMILWAUKEE

$109.00
50 mg

Available to ship TODAYfromMILWAUKEE

$375.00

About This Item

Empirical Formula (Hill Notation):
C26H29NO2
CAS Number:
68392-35-8
Molecular Weight:
387.51
UNSPSC Code:
51111800
PubChem Substance ID:
24895736
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder
Storage condition:
desiccated, protect from light

$109.00

Available to ship TODAYDetails

​
Request a Custom Order
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

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

Quality Segment

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

Gene Information

General description

4-Hydroxytamoxifen (4-OHT), a first-generation selective estrogen receptor modulator (SERM), acts as an antagonist in breast cancer cells but exhibits estrogen-like effects in the uterus and bone. It is an active metabolite of the pro-drug tamoxifen (TAM), functioning as an estrogen receptor antagonist. 4-OHT binds to estrogen receptors to inhibit estradiol-induced cell proliferation without inducing cytotoxicity. It is a metabolite of the antiestrogen, tamoxifen and exhibits a higher affinity than tamoxifen and its other metabolites for binding to estrogen receptors, making it 50 to 100 times more potent in inhibiting cell proliferation in normal human breast cells and breast cancer cell lines in culture.

4-OHT effectively inhibited cell growth in the absence of estrogen when cell proliferation was stimulated by insulin or epidermal growth factor. 4-OHT inhibits lipid peroxidation within cell membranes and shows peroxyl radical scavenging activity.

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.

Compare Similar Items

View Full Comparison

Show Differences

1 of 1

This Item
T176H790494873
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

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

Supelco

94873

4-Hydroxytamoxifen

description

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

description

analytical standard, (E) and (Z) isomers (50:50)

description

≥98% Z isomer

description

(E) and (Z) isomers (50:50), analytical standard

form

powder

form

powder

form

powder

form

-

assay

≥98% (HPLC)

assay

-

assay

≥98% (HPLC)

assay

≥97.5% (HPLC)

Quality Level

300

Quality Level

200

Quality Level

300

Quality Level

100

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

-

solubility

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

solubility

ethanol: 20 mg/mL

solubility

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

solubility

-

storage condition

desiccated, protect from light

storage condition

-

storage condition

protect from light, desiccated

storage condition

-

Still not finding the right product?

Explore all of our products under 4-Hydroxytamoxifen

Pictograms

Health hazardExclamation mark
GHS08,GHS07

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

11 - Combustible Solids

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

PPE (personal protective equipment)

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

It looks like we've run into a problem, but you can still download Certificates of Analysis from our Documents section.

If you need assistance, please contact Customer Support

Already Own This Product?

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

Visit the Document Library

1 Review This action will navigate to reviews.

Questions

1–2 of 2 Questions  

  1. How do you suggest to solubilize it for in vivo applications? Also, which would be the best via for that? Thanks in advance.

    1 answer

    1. The solubility of this product is tested at 25 mg/mL in Ethanol, with heating. Stock solutions may be stored at –20 °C, protected from light. Further dilutions may be made with saline or other aqueous buffers. Sterile filtration prior to administration is required. In vivo testing has not been performed on this material. The best method would depend on the preferred route. Various published animal protocols describe transferring the compound into corn oil after removal of the ethanol for intraperitoneal injection.

      Please see the link below to review an example protocol available at ‘Bio-Protocol’:
      https://bio-protocol.org/exchange/preprintdetail?id=1565&type=3

      Please see the following link to review additional information available in the product datasheet:
      https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/405/857/h6278dat.pdf

      Helpful?

  2. How stable is 4_OH tamoxifen reconstituted? Can it survive freeze thaw cycles?

    1 answer

    1. Please see the link below to access the product datasheet which includes solubility and solution storage information. While this product has not been tested for stability following multiple freeze/thaw cycles, as a general rule it is best to avoid multiple cycles.

      https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/405/857/h6278dat.pdf

      Helpful?

Reviews

1 of 1 reviewers took part in a promotion

Active Filters

  1. London, UK
    • Review 1
    • Vote 1
    5 out of 5 stars.

    Nothing to complain about

    Fast delivery, very satisfied, correct amount, all good

    Helpful?