MW 387.5 Da, Purity >98%. Potent and selective estrogen receptor antagonist (IC50 = 7 nM). Active metabolite of (Z)-tamoxifen (ab120656) and exhibits higher potency in vitro. Shows antiproliferative effect (IC50 = 27 μM). Induces p21 nuclear localization.
Images
Publications
Filter by
- Cellular and molecular life sciences : CMLS 81:512024Combination of blockade of endothelin signalling and compensation of IGF1 expression protects the retina from degeneration.Applications:Unspecified applicationReactive species:Unspecified reactive speciesNaoya Shigesada,Naoya Shikada,Manabu Shirai,Michinori Toriyama,Fumiaki Higashijima,Kazuhiro Kimura,Toru Kondo,Yasumasa Bessho,Takuma Shinozuka,Noriaki SasaiPubMed 38252153
- Nature communications 14:49912023An ATR-PrimPol pathway confers tolerance to oncogenic KRAS-induced and heterochromatin-associated replication stress.Applications:Unspecified applicationReactive species:Unspecified reactive speciesTaichi Igarashi,Marianne Mazevet,Takaaki Yasuhara,Kimiyoshi Yano,Akifumi Mochizuki,Makoto Nishino,Tatsuya Yoshida,Yukihiro Yoshida,Nobuhiko Takamatsu,Akihide Yoshimi,Kouya Shiraishi,Hidehito Horinouchi,Takashi Kohno,Ryuji Hamamoto,Jun Adachi,Lee Zou,Bunsyo ShiotaniPubMed 37591859
- Bio-protocol 12:2022Microscopic Detection of DNA Synthesis in Early Mitosis at Repetitive Sequences in Human Cells.Applications:Unspecified applicationReactive species:Unspecified reactive speciesKazumasa Yoshida,Riko Ishimoto,Masatoshi FujitaPubMed 36213106
- EMBO reports 22:e489612021EVL regulates VEGF receptor-2 internalization and signaling in developmental angiogenesis.Applications:Unspecified applicationReactive species:Unspecified reactive speciesJoana Zink et. al.PubMed 33512764
- Molecular cell :2021A tamoxifen receptor within a voltage-gated sodium channel.Applications:Unspecified applicationReactive species:Unspecified reactive speciesAltin Sula et. al.PubMed 33503406
- Nature 582:253-2582020Basement membrane remodelling regulates mouse embryogenesis.Applications:Unspecified applicationReactive species:Unspecified reactive speciesChristos Kyprianou et. al.PubMed 32523119
- Molecular biology of the cell 31:768-7812020Integrin-linked kinase regulates melanosome trafficking and melanin transfer in melanocytes.Applications:Unspecified applicationReactive species:Unspecified reactive speciesMelissa Crawford,Nancy Liu,Elahe Mahdipour,Kevin Barr,Bryan Heit,Lina DagninoPubMed 32049584
- The Journal of investigative dermatology 140:425-434.e102019Essential Role for Integrin-Linked Kinase in Melanoblast Colonization of the Skin.Applications:Unspecified applicationReactive species:Unspecified reactive speciesMelissa Crawford et. al.PubMed 31330146
- Scientific reports 9:91002019Iron-mediated aggregation and toxicity in a novel neuronal cell culture model with inducible alpha-synuclein expression.Applications:Unspecified applicationReactive species:Unspecified reactive speciesMartin Bartels et. al.PubMed 31235814
- Theranostics 9:2183-21972019High OGT activity is essential for MYC-driven proliferation of prostate cancer cells.Applications:Unspecified applicationReactive species:Unspecified reactive speciesHarri M Itkonen et. al.PubMed 31149037
Key facts
- CAS number
- 68047-06-3
- Purity
- > 98%
- Form
- Solid
- Molecular weight
- 387.5 Da
- Molecular formula
- C26H29NO2
- PubChem identifier
- 449459
- Nature
- Synthetic
Alternative names
Atherosclerosis, susceptibility to, included, DKFZp686N23123, DKFZp781L1617, ER, ER-alpha, ER-beta, ERR B2, ERR G2, ERR a, ERR b, ERR beta-2, ERR gamma-2, ERR-alpha, ERR-beta, ERR1 protein, ERR1_HUMAN, ERR2_HUMAN, ERR3_HUMAN, ERRgamma, ER[a], ER[b], ESR, ESR B, ESR BETA, ESR L2, ESR1_HUMAN, ESR2_HUMAN, ESRA, ESRL 1, ESRR A, ESRRG, ESTR B, Era, Erb, Erb2, Esrrb, Estr, Estra, Estradiol Receptor alpha, Estradiol Receptor beta, Estradiol receptor, Estrogen Receptor 1, Estrogen Receptor 2, Estrogen receptor, Estrogen receptor 1 (alpha), Estrogen receptor 2 (ER beta), Estrogen receptor 2 ER beta, Estrogen receptor alpha, Estrogen receptor beta, Estrogen receptor beta 4, Estrogen receptor related 1, Estrogen receptor related 2, Estrogen receptor-like 1, Estrogen receptor-like 2, Estrogen receptor-related protein 3, Estrogen resistance, included, Estrogen-related receptor alpha, Estrogen-related receptor beta, Estrogen-related receptor gamma, Estrra, Estrrb, FLJ16023, HDL cholesterol, augmented response of, to hormone replacement, included, KIAA0832, Myocardial infarction, susceptibility to, included, NR3A1, NR3A2, NR3B1, NR3B3, Nr3b2, Nuclear receptor ERRB2, Nuclear receptor subfamily 3 group A member 1, Nuclear receptor subfamily 3 group A member 2, Nuclear receptor subfamily 3 group B member 1, Nuclear receptor subfamily 3 group B member 2, Nuclear receptor subfamily 3 group B member 3, OTTHUMP00000017718, OTTHUMP00000017719, Orphan nuclear receptor, RNESTROR, Steroid hormone receptor ERR 2, Steroid hormone receptor ERR1, estrogen nuclear receptor beta variant a, estrogen nuclear receptor beta variant b, estrogen receptor related receptor alpha, hERR1
Recommended products
MW 387.5 Da, Purity >98%. Potent and selective estrogen receptor antagonist (IC50 = 7 nM). Active metabolite of (Z)-tamoxifen (ab120656) and exhibits higher potency in vitro. Shows antiproliferative effect (IC50 = 27 μM). Induces p21 nuclear localization.
Key facts
- CAS number
- 68047-06-3
- Purity
- > 98%
- Form
- Solid
- Molecular weight
- 387.5 Da
- Molecular formula
- C26H29NO2
- PubChem identifier
- 449459
- Nature
- Synthetic
- Solubility
Soluble in ethanol to 50 mM.
Soluble in DMSO to 100 mM.
- Biochemical name
- 4-Hydroxytamoxifen
- Biological description
Potent and selective estrogen receptor antagonist (IC50 = 7 nM). Active metabolite of (Z)-tamoxifen (ab120656) and exhibits higher potency in vitro. Shows antiproliferative effect (IC50 = 27 μM). Induces p21 nuclear localization.
- Canonical SMILES
- CCC(=C(C1=CC=C(C=C1)O)C2=CC=C(C=C2)OCCN(C)C)C3=CC=CC=C3
- Isomeric SMILES
- CC/C(=C(\C1=CC=C(C=C1)O)/C2=CC=C(C=C2)OCCN(C)C)/C3=CC=CC=C3
- InChI
- 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-
- InChIKey
- TXUZVZSFRXZGTL-QPLCGJKRSA-N
- IUPAC name
- 4-[(Z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol
Storage
- Shipped at conditions
- Ambient - Can Ship with Ice
- Appropriate short-term storage conditions
- -20°C
- Appropriate long-term storage conditions
- -20°C
- Storage information
- Store under desiccating conditions, The product can be stored for up to 12 months
Supplementary info
- This supplementary information is collated from multiple sources and compiled automatically.
- Activity summary
The estrogen receptor family includes Estrogen Receptor (ER) Estrogen Receptor beta (ERβ) and Estrogen Related Receptors alpha beta and gamma (ERRα ERRβ ERRγ). These nuclear receptors function as transcription factors activated by estrogen with ER being extensively studied. ER has two subtypes ERα and ERβ with masses approximately 66 kDa and 59 kDa respectively. These receptors are largely expressed in reproductive tissues but also in the brain bone and cardiovascular system. ERRs related yet distinct from ERs do not actually bind estrogens and function independently of these ligands.
- Biological function summary
Estrogen receptors regulate gene expression and play essential roles in various physiological processes. They often form receptor complexes to exert their effects. These receptors impact cell reproduction differentiation and development processes influencing tissue homeostasis. ERα is particularly important in breast tissue affecting growth and function and interacts with co-regulator proteins to mediate estrogen responses. ERRs while sharing structural similarities regulate genes involved in energy metabolism and mitochondrial function.
- Pathways
The estrogen receptors participate in the estrogen signaling pathway influencing growth and development in response to hormonal changes. They interact strongly with coactivators and corepressors to modulate gene transcription. MAPK/ERK and PI3K/Akt are notable pathways through which ERs exert effects often involving cross-talk with Growth Factor Receptors. ERRs participate in metabolic reprogramming pathways associating with genes that regulate oxidative phosphorylation. These pathways reveal how receptor actions are integrated and regulated in cellular contexts.
- Associated diseases and disorders
Estrogen receptors are significantly involved in breast cancer and osteoporosis. ERα is often overexpressed in many breast cancer types and serves as a target for compounds like 4-hydroxytamoxifen (4-OHT) a selective estrogen receptor modulator. This interaction inhibits estrogen stimulation of cancer cells. ERRs are implicated in metabolic disorders due to their role in energy homeostasis. For osteoporosis the receptor's influence on bone density and turnover points to key therapeutic targets. In breast cancer the relationship between ERα and proteins like Her2/neu can affect treatment responses and prognosis illustrating the critical role estrogen receptors play in disease mechanisms.
Product promise
We are dedicated to supporting your work with high quality reagents and we are here for you every step of the way should you need us.
In the unlikely event of one of our products not working as expected, you are covered by our product promise.
Full details and terms and conditions can be found here:
Terms & Conditions.
1 product image
Chemical Structure - (Z)-4-Hydroxytamoxifen, estrogen receptor modulator (ab141943)
2D chemical structure image of ab141943, (Z)-4-Hydroxytamoxifen, estrogen receptor modulator
Downloads
Product protocols
- Visit the general protocols
- Visit troubleshooting
Please note: All products are 'FOR RESEARCH USE ONLY. NOT FOR USE IN DIAGNOSTIC OR THERAPEUTIC PROCEDURES'.
For licensing inquiries, please contact partnerships@abcam.com