4-(di(1H-indol-3-yl)Methyl)phenol
- Product Name
- 4-(di(1H-indol-3-yl)Methyl)phenol
- CAS No.
- 151358-47-3
- Chemical Name
- 4-(di(1H-indol-3-yl)Methyl)phenol
- Synonyms
- C-DIM8;DIM-C-pPhOH;DIM-C-pPhOH(CDIM8);DIM-C-pPhOH, 10 mM in DMSO;4-(di(1H-indol-3-yl)Methyl)phenol;4-[bis(1H-indol-3-yl)methyl]phenol;Phenol, 4-(di-1H-indol-3-ylmethyl)-;4-(di-1H-indole-3-ylmethyl)benzenephenol;1,1-Bis(3'-indolyl)-1-(p-hydroxyphenyl)methane;1,1-bis(3'-indolyl)-1-(4-hydroxyphenyl)methane
- CBNumber
- CB12682261
- Molecular Formula
- C23H18N2O
- Formula Weight
- 338.4
- MOL File
- 151358-47-3.mol
4-(di(1H-indol-3-yl)Methyl)phenol Property
- Melting point:
- 122-124 °C
- Boiling point:
- 610.2±50.0 °C(Predicted)
- Density
- 1.321±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Soluble in DMSO (35 mg/ml); ethanol (35 mg/ml)
- form
- solid
- pka
- 9.98±0.26(Predicted)
- color
- Pink
- Stability:
- Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months.
- InChI
- 1S/C23H18N2O/c26-16-11-9-15(10-12-16)23(19-13-24-21-7-3-1-5-17(19)21)20-14-25-22-8-4-2-6-18(20)22/h1-14,23-26H
- InChIKey
- QCPDFNWJBQMXLI-UHFFFAOYSA-N
- SMILES
- OC1=CC=C(C(C2=CNC3=C2C=CC=C3)C4=CNC5=C4C=CC=C5)C=C1
Safety
- WGK Germany
- WGK 3
- Storage Class
- 11 - Combustible Solids
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- D6003
- Product name
- 4-[Di(1H-indol-3-yl)methyl]phenol
- Packaging
- 250MG
- Price
- $102
- Updated
- 2026/03/19
- Product number
- 6377
- Product name
- DIM-C-pPhOH
- Purity
- ≥98%(HPLC)
- Packaging
- 25
- Price
- $371
- Updated
- 2021/12/16
- Product number
- 6377
- Product name
- DIM-C-pPhOH
- Purity
- ≥98%(HPLC)
- Packaging
- 5
- Price
- $95
- Updated
- 2021/12/16
- Product number
- 105340
- Product name
- 4-(Di(1H-indol-3-yl)methyl)phenol
- Packaging
- 2g
- Price
- $975
- Updated
- 2021/12/16
- Product number
- CM265482
- Product name
- 4-(Di(1H-indol-3-yl)methyl)phenol
- Purity
- 95%+
- Packaging
- 5g
- Price
- $1234
- Updated
- 2021/12/16
4-(di(1H-indol-3-yl)Methyl)phenol Chemical Properties,Usage,Production
Description
C-DIM 8 (151358-47-3) is an antagonist of the orphan nuclear receptor Nur77 (NR4A1, TR3).1 Induces reactive oxygen species and ER stress in pancreatic cancer cells.2 C-DIM 8 mimics the effect of Nur77 knockdown in non-small-cell lung cancer A549 and H460 cells, inhibiting cell growth and inducing apoptosis which was accompanied by decreased expression of survivin and inhibition of mTORC1 signaling.3 Inhibits the expression of β1- and β3-integrin and blocks integrin-dependent breast cancer cell migration.4 Decreases expression of the histone methyltransferase G9A (EHMT2) in a variety of cancer cell lines.5
Uses
DIM-C-pPhOH is a nuclear receptor 4A1 (NR4A1) antagonist. DIM-C-pPhOH inhibits cancer cell growth and mTOR signaling, induce apoptosis and cellular stress. DIM-C-pPhOH reduces cell proliferation with IC50 values of 13.6 μM and 13.0 μM for ACHN cells and 786-O cells, respectively[1].
Synthesis
120-72-9
123-08-0
151358-47-3
GENERAL METHODS: BiVO4 nanoparticles (BiVO4-NPs, 30 mg) were added to a mixture containing indole or 2-methylindole (2 mmol) with aldehydes (1 mmol). The reaction mixture was stirred at 80 °C for an appropriate time under solvent-free conditions. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was diluted with 30 mL of hot ethanol and the catalyst was recovered by filtration and washed with ethanol (5 mL). The solvent was evaporated under reduced pressure and the remaining solid was recrystallized by a solvent mixture of ethanol/water (95:5, v/v) to give the pure product 4-(bis(1H-indol-3-yl)methyl)phenol. The spectral and physical data of all the products were in agreement with those reported in the literature and corresponded to samples prepared according to previously reported methods.
in vivo
DIM-C-pPhOH (30 mg/kg; oral gavage; daily; for 50 days; male athymic nude mice) treatment results in a significant inhibition of tumor growth[1].
| Animal Model: | Male athymic nude mice (aged 6-7 weeks) injected with ACHN cells[1] |
| Dosage: | 30 mg/kg/day |
| Administration: | Oral gavage; daily; for 50 days |
| Result: | Resulted in a significant inhibition of tumor growth. |
IC 50
Nur77/NR4A1
storage
Store at -20°C
References
[1] SUDHAKAR CHINTHARLAPALLI. Activation of Nur77 by selected 1,1-Bis(3’-indolyl)-1-(p-substituted phenyl)methanes induces apoptosis through nuclear pathways.[J]. The Journal of Biological Chemistry, 2005, 280 26: 24903-24914. DOI:10.1074/jbc.m500107200
[2] SYNG-OOK LEE. The orphan nuclear receptor NR4A1 (Nur77) regulates oxidative and endoplasmic reticulum stress in pancreatic cancer cells.[J]. Molecular Cancer Research, 2014, 12 4: 527-538. DOI:10.1158/1541-7786.mcr-13-0567
[3] S-O LEE. The nuclear receptor TR3 regulates mTORC1 signaling in lung cancer cells expressing wild-type p53[J]. Oncogene, 2011, 31 27: 3265-3276. DOI:10.1038/onc.2011.504
[4] E. HEDRICK. NR4A1 Antagonists Inhibit β1-Integrin-Dependent Breast Cancer Cell Migration[J]. Molecular and Cellular Biology, 2016, 36 1: 1383-1394. DOI:10.1128/mcb.00912-15
[5] RUPESH SHRESTHA. The Histone Methyltransferase Gene G9A Is Regulated by Nuclear Receptor 4A1 in Alveolar Rhabdomyosarcoma Cells.[J]. Molecular Cancer Therapeutics, 2021, 20 3: 612-622. DOI:10.1158/1535-7163.mct-20-0474
4-(di(1H-indol-3-yl)Methyl)phenol Preparation Products And Raw materials
Raw materials
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