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I7256

Sigma-Aldrich

Indole-3-carbinol

Sinónimos:

3-Indolemethanol

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About This Item

Fórmula empírica (notación de Hill):
C9H9NO
Número de CAS:
700-06-1
Peso molecular:
147.17
EC Number:
211-836-2
MDL number:
MFCD00005632
UNSPSC Code:
12352005
PubChem Substance ID:
24896113
NACRES:
NA.25

Quality Level

100

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

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Chemoprevention of chemically-induced mammary carcinogenesis by indole-3-carbinol.
Grubbs CJ, et al.
Anticancer Research, 15(3), 709-716 (1995)
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)
Catherine J Leader et al.
PloS one, 14(8), e0220837-e0220837 (2019-08-14)
Is global longitudinal strain (GLS) a more accurate non-invasive measure of histological myocardial fibrosis than left ventricular ejection fraction (LVEF) in a hypertensive rodent model. Hypertension results in left ventricular hypertrophy and cardiac dysfunction. Speckle-tracking echocardiography has emerged as a
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
Youngshim Choi et al.
The Journal of nutritional biochemistry, 23(12), 1732-1739 (2012-05-10)
Indole-3-carbinol (I3C) is a compound found in high concentrations in Brassica family vegetables, including broccoli, cauliflower and cabbage, and is regarded as a promising chemopreventive agent against various cancers. This study assesses the protective effect of I3C against diet-induced obesity
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