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Safety Information

D9568

Sigma-Aldrich

3,3′-Diindolylmethane

≥98% (HPLC)

Synonym(s):

3,3′-Bisindolylmethane, DIM

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About This Item

Empirical Formula (Hill Notation):
C17H14N2
CAS Number:
1968-05-4
Molecular Weight:
246.31
MDL number:
MFCD00195766
UNSPSC Code:
12352200
PubChem Substance ID:
329798906
NACRES:
NA.25

Quality Level

100

Assay

≥98% (HPLC)

form

powder

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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Application


  • 3,3′-Diindolylmethane inhibits Th17 cell differentiation via impairing IRF-7-mediated plasmacytoid dendritic cell activation in imiquimod-induced psoriasis mice.: The research indicates that 3,3′-Diindolylmethane can effectively inhibit Th17 cell differentiation, offering a potential therapeutic approach for treating psoriasis by targeting plasmacytoid dendritic cell pathways (Rasool et al., 2024).

  • Protective effect of diindolylmethane-enriched dietary cabbage against doxorubicin-induced cardiotoxicity in mice.: This study highlights the cardioprotective effects of a diindolylmethane-enriched diet in mice, offering a dietary approach to mitigate the cardiotoxic effects of doxorubicin, a common chemotherapeutic agent (Natesh et al., 2024).

  • Nanoformulated 3′-diindolylmethane modulates apoptosis, migration, and angiogenesis in breast cancer cells.: The investigation into nanoformulated 3′-diindolylmethane shows it significantly influences apoptosis, migration, and angiogenesis, suggesting its utility in targeted cancer therapies (Harakeh et al., 2024).

  • Design, synthesis, and biological evaluation of 3,3′-diindolylmethane N-linked glycoconjugate as a leishmanial topoisomerase IB inhibitor with reduced cytotoxicity.: Research presents a synthesized glycoconjugate of 3,3′-Diindolylmethane as an effective inhibitor of leishmanial topoisomerase IB, demonstrating reduced cytotoxicity and potential as a therapeutic agent (Kour et al., 2023).

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335,H413

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

D9568-5G:
D9568-VAR:
D9568-BULK:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sanjeev Banerjee et al.
Mutation research, 728(1-2), 47-66 (2011-06-28)
Emerging evidence provide credible support in favor of the potential role of bioactive products derived from ingesting cruciferous vegetables such as broccoli, brussel sprouts, cauliflower and cabbage. Among many compounds, 3,3'-diindolylmethane (DIM) is generated in the acidic environment of the
Yiwei Li et al.
Antioxidants & redox signaling, 19(2), 139-150 (2013-02-09)
Oxidative stress has been mechanistically linked with aging and chronic diseases, including cancer. In fact, oxidative stress status, chronic disease-related inflammation, and cancer occurred in the aging population are tightly correlated. It is well known that the activation of nuclear
Timothy E Hoffman et al.
Archives of toxicology, 93(3), 635-647 (2018-12-21)
The aryl hydrocarbon receptor (AhR) is a nuclear receptor that facilitates a wide transcriptional response and causes a variety of adaptive and maladaptive physiological functions. Such functions are entirely dependent on the type of ligand activating it, and therefore, the
Xueli Tian et al.
Cancer letters, 448, 20-30 (2019-02-05)
3,3'-Diindolymethane (DIM) is a dimeric condensation product of indole-3-carbinol (I3C) that is found in broccoli and cabbage. Although DIM has been reported to exhibit anticancer properties against multiple tumor types, the direct target proteins of DIM have not been fully
K Hempstalk et al.
Journal of dairy science, 98(8), 5262-5273 (2015-06-16)
The ability to accurately predict the conception outcome for a future mating would be of considerable benefit for producers in deciding what mating plan (i.e., expensive semen or less expensive semen) to implement for a given cow. The objective of
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