4-Hydroxytamoxifen (E) and (Z) isomers (50:50)
Product overview
Name | 4-Hydroxytamoxifen (E) and (Z) isomers (50:50) |
Description | Synthetic estrogen receptor ligand. Widely used in genome engineering (e.g. CreER/ CRISPR-Cas9). |
Alternative names | 4-HT, 4-OHT, 4-OH-TAM, OHT, TAM, 4-Hydroxytamoxifen |
Purity | >98% |
Biological Data
Biological description | Cell permeable, synthetic estrogen receptor ligand. Widely used in genome engineering. (E) and (Z) isomer mix (50:50).
De facto standard compound in drug-inducible manipulation of CreER recombinase. Allows external temporal control of Cre activity in vivo. May also be used for TRAPing / in the TRAP / TRAP2 system (Targeted recombination in active populations).
Activates an inactived Cas9 nuclease (rendered inactive by insertion of a 4-OHT dependent-intein) to reduce off-target CRISPR-mediated gene editing (once bound with 4-OHT, conditionally active Cas9s modify target genomic sites with ~25-fold higher specificity than wild-type Cas9).
≥70% Z isomer (remainder primarily E-isomer) 4-Hydroxytamoxifen also available. |
Solubility & Handling
Storage instructions | -20°C |
Solubility overview | Soluble in DMSO (100 mM) and in ethanol (50 mM) |
Handling | Storage of solid
Storage of solutions
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Important | This product is for RESEARCH USE ONLY and is not intended for therapeutic or diagnostic use. Not for human or veterinary use. |
Chemical Data
Chemical name | 4-(1-[4-(Dimethylaminoethoxy)phenyl]-2-phenyl-1-butenyl)phenol |
Molecular Weight | 387.51 |
Chemical structure | |
Molecular Formula | C26H29NO2 |
CAS Number | 68392-35-8 |
PubChem identifier | 449459 |
SMILES | CC/C(=C(\C1=CC=C(C=C1)O)/C2=CC=C(C=C2)OCCN(C)C)/C3=CC=CC=C3 |
Source | Synthetic |
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 |
Appearance | Off-white solid |
References for 4-Hydroxytamoxifen (E) and (Z) isomers (50:50)
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A chemical-inducible CRISPR-Cas9 system for rapid control of genome editing.
Liu et al (2016) Nat Chem Biol 12(11) : 980-987. -
Small molecule-triggered Cas9 protein with improved genome-editing specificity.
Small molecule-triggered Cas9 protein with improved genome-editing specificity. (2015) Nat Chem Biol 11(5) : 316-8. -
Simple and efficient production of (Z)-4-hydroxytamoxifen, a potent estrogen receptor modulator.
Yu and Forman (2003) J Org Chem 68(24) : 9489-91. -
A monohydroxylated metabolite of tamoxifen with potent antioestrogenic activity.
Jordan et al (1977) J Endocrinol 75(2) : 305-16.