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I7256

Sigma-Aldrich

Indole-3-carbinol

Synonym(s):

3-Indolemethanol

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About This Item

Empirical Formula (Hill Notation):
C9H9NO
CAS Number:
700-06-1
Molecular Weight:
147.17
EC Number:
211-836-2
MDL number:
MFCD00005632
UNSPSC Code:
12352005
PubChem Substance ID:
24896113
NACRES:
NA.25

mp

96-99 °C (lit.)

storage temp.

2-8°C

SMILES string

OCc1c[nH]c2ccccc12

InChI

1S/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2

InChI key

IVYPNXXAYMYVSP-UHFFFAOYSA-N

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General description

Indole-3-carbinol is a novel secondary plant metabolite produced in cruciferous vegetables, such as cabbage, cauliflower and brussels sprouts.

Application

Indole-3-carbinol has been used for encapsulation with poly-lactic-co-glycolic acid (PLGA), to study its in-vitro anti-cancerogenic effects on breast adenocarcinoma epithelial (MCF7), colon adenocarcinoma epithelial (Caco2), prostate carcinoma epithelial (PC3) cells. It has also been used as a cytochrome P4501A (CYP1A) inducer.

Biochem/physiol Actions

Indole-3-carbinol (I3C) activates aryl hydrocarbon receptor (AhR) and induces G1 cell cycle arrest and apoptosis. Thus, it acts as a potential anti-cancer agent. In addition, it induces estradiol metabolism by stimulating cytochrome P450 enzymes. Therefore, I3C is considered to be a potent chemotherapeutic for various types of cancer including, breast, prostate, colon cancer, and leukemia.
Inhibits cancinogenesis at the initiation stage. Has be shown to inhibit carcinogenesis in several animal species, but it enhances tumor incidence if administered at a post-initiation stage. Found in cruciferous vegetables.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Profiling the hepatic effects of flutamide in rats: a microarray comparison with classical aryl hydrocarbon receptor ligands and atypical CYP1A inducers
Coe KJ, et al.
Drug Metabolism and Disposition, 34(7), 1266-1275 (2006)
PLGA encapsulation and radioiodination of indole-3-carbinol: investigation of anticancerogenic effects against MCF7, Caco2 and PC3 cells by in vitro assays
Yildiz G, et al.
J. Radioanal. Nucl. Chem., 311(2), 1043-1052 (2017)
Aromatic hydrocarbon responsiveness-receptor agonists generated from indole-3-carbinol in vitro and in vivo: comparisons with 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin.
Bjeldanes LF, et al.
Proceedings of the National Academy of Sciences of the USA, 88(21), 9543-9547 (1991)
Young S Kim et al.
The Journal of nutritional biochemistry, 16(2), 65-73 (2005-02-01)
Mounting preclinical and clinical evidence indicate that indole-3-carbinol (I3C), a key bioactive food component in cruciferous vegetables, has multiple anticarcinogenic and antitumorigenic properties. Evidence that p21, p27, cyclin-dependent kinases, retinoblastoma, Bax/Bcl-2, cytochrome P-450 1A1 and GADD153 are targets for I3C
Indole-3-carbinol induces G1 cell cycle arrest and apoptosis through aryl hydrocarbon receptor in THP-1 monocytic cell line
Mohammadi S, et al.
Journal of Receptor and Signal Transduction Research, 37(5), 506-514 (2017)
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