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3,3′-Diindolylmethane

analytical standard

Synonym(s):

3,3′-Bisindolylmethane, DIM

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About This Item

Empirical Formula (Hill Notation):
C17H14N2
CAS Number:
Molecular Weight:
246.31
MDL number:
UNSPSC Code:
41116107
NACRES:
NA.24

grade

analytical standard

Quality Level

Assay

≥97.5% (HPLC)

shelf life

limited shelf life, expiry date on the label

application(s)

food and beverages

format

neat

storage temp.

2-8°C

SMILES string

C(c1c[nH]c2ccccc12)c3c[nH]c4ccccc34

InChI

1S/C17H14N2/c1-3-7-16-14(5-1)12(10-18-16)9-13-11-19-17-8-4-2-6-15(13)17/h1-8,10-11,18-19H,9H2

InChI key

VFTRKSBEFQDZKX-UHFFFAOYSA-N

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General description

3,3′-Diindolylmethane, a dimer of indole-3-carbinol, is a component of cruciferous vegetables. It is known to exhibit anticancer effects.

Application

3,3′-Diindolylmethane may be used as a model substrate to analyze the role of 3,3′-diindolylmethane in inducing apoptosis in human cancer cells.

Biochem/physiol Actions

Acid-catalyzed reaction product of a phytochemical naturally found in Brassicaceae, indole-3-carbinol. It functions as an antitumor agent. This derivative can both directly stimulate apoptosis at relatively high concentrations and sensitize TRAIL-induced apoptosis in human cancer cells. DIM induces a G1 cell cycle arrest in human breast cancer MCF-7 cells by a mechanism that includes increased expression of p21. DIM is a strong mitochondrial H+-ATPase inhibitor. The function of DIM and its derivatives as a new plant growth promoter has been studied in an eco-friendly system.

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Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Aquatic Chronic 4 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Plant derived 3, 3′-diindolylmethane is a strong androgen antagonist in human prostate cancer cells.
Le HT, et al.
The Journal of Biological Chemistry (2003)
3, 3′-Diindolylmethane induces apoptosis in human cancer cells.
Ge X, et al.
Biochemical and Biophysical Research Communications, 228(1), 153-158 (1996)

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