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)-;1,1-Bis(3'-indolyl)-1-(p-hydroxyphenyl)methane;1,1-bis(3'-indolyl)-1-(4-hydroxyphenyl)methane;inhibit,receptor,Inhibitor,β1-integrin,mTOR,cancer,DIMCpPhOH,signaling,nuclear,xenografts,Apoptosis,DIM C pPhOH,stress
CBNumber: CB12682261
Molecular Formula: C23H18N2O
Formula Weight: 338.4
MOL File: 151358-47-3.mol

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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.

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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.

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N-Bromosuccinimide Price

TCI Chemical

Product number: D6003
Product name: 4-[Di(1H-indol-3-yl)methyl]phenol
Packaging: 250MG
Price: $128
Updated: 2025/07/31

Tocris

Product number: 6377
Product name: DIM-C-pPhOH
Purity: ≥98%(HPLC)
Packaging: 25
Price: $371
Updated: 2021/12/16

Tocris

Product number: 6377
Product name: DIM-C-pPhOH
Purity: ≥98%(HPLC)
Packaging: 5
Price: $95
Updated: 2021/12/16

Matrix Scientific

Product number: 105340
Product name: 4-(Di(1H-indol-3-yl)methyl)phenol
Packaging: 2g
Price: $975
Updated: 2021/12/16

Chemenu

Product number: CM265482
Product name: 4-(Di(1H-indol-3-yl)methyl)phenol
Purity: 95%+
Packaging: 5g
Price: $1234
Updated: 2021/12/16

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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

Preparation Products

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4-(di(1H-indol-3-yl)Methyl)phenol Suppliers

China 80 India 1 United Kingdom 1 United States 8 Global 90

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151358-47-3, 4-(di(1H-indol-3-yl)Methyl)phenolRelated Search:

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4-(di(1H-indol-3-yl)Methyl)phenol

DIM-C-pPhOH

4-[bis(1H-indol-3-yl)methyl]phenol

C-DIM8

1,1-Bis(3'-indolyl)-1-(p-hydroxyphenyl)methane

DIM-C-pPhOH(CDIM8)

Phenol, 4-(di-1H-indol-3-ylmethyl)-

inhibit,receptor,Inhibitor,β1-integrin,mTOR,cancer,DIMCpPhOH,signaling,nuclear,xenografts,Apoptosis,DIM C pPhOH,stress

1,1-bis(3'-indolyl)-1-(4-hydroxyphenyl)methane

DIM-C-pPhOH, 10 mM in DMSO

151358-47-3