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About This Item
Empirical Formula (Hill Notation):
C9H9NO
CAS Number:
Molecular Weight:
147.17
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.25
Recommended Products
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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)
Chemoprevention of chemically-induced mammary carcinogenesis by indole-3-carbinol.
Grubbs CJ, et al.
Anticancer Research, 15(3), 709-716 (1995)
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
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