I7256
Indole-3-carbinol
Synonym(s):
3-Indolemethanol
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About This Item
Empirical Formula (Hill Notation):
C9H9NO
CAS Number:
Molecular Weight:
147.17
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352005
EC Number:
211-836-2
MDL number:
InChI key
IVYPNXXAYMYVSP-UHFFFAOYSA-N
InChI
1S/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2
SMILES string
OCc1c[nH]c2ccccc12
mp
96-99 °C (lit.)
storage temp.
2-8°C
Quality Level
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2
Storage Class
11 - Combustible Solids
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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)
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)
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)
Effects of dietary indole-3-carbinol on estradiol metabolism and spontaneous mammary tumors in mice
Bradlow HL, et al.
Carcinogenesis, 12(9), 1571-1574 (1991)
Oliver Schanz et al.
International journal of molecular sciences, 21(9) (2020-05-06)
A diet rich in vegetables and fruit is generally considered healthy because of a high content of phytochemicals, vitamins, and fiber. The phytochemical indole-3-carbinol (I3C), a derivative of glucobrassicin, is sold as a dietary supplement promising diverse health benefits. I3C
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