ChemicalBook > CAS DataBase List > Indole-3-carbinol

Indole-3-carbinol

CAS No.700-06-1
Chemical Name:Indole-3-carbinol
CBNumber:CB7295605
Molecular Formula:C9H9NO
Formula Weight:147.17
MOL File:700-06-1.mol

Indole-3-carbinol Property

Melting point 96-99 °C (lit.)
Boiling point 267.28°C (rough estimate)
Density 1.1135 (rough estimate)
refractive index 1.5670 (estimate)
storage temp. 2-8°C
solubility soluble in Methanol
form Crystalline Powder or Flakes
pka 15.10±0.10(Predicted)
color Off-white to yellow-orange
BRN 121323
Stability 2-80C
InChI InChI=1S/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2
InChIKey IVYPNXXAYMYVSP-UHFFFAOYSA-N
SMILES N1C2=C(C=CC=C2)C(CO)=C1
LogP 1.366 (est)
CAS DataBase Reference 700-06-1(CAS DataBase Reference)
EWG's Food Scores 1
NCI Dictionary of Cancer Terms indole-3-carbinol
FDA UNII C11E72455F
NCI Drug Dictionary indole-3-carbinol
UNSPSC Code 12352005
NACRES NA.25

Safety

Hazard Codes :Xi
Risk Statements :36/38
Safety Statements :26-36
WGK Germany :3
RTECS :NL9483000
Hazard Note :Irritant
HS Code :29339900

NFPA 704:

	1
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H315-H319
Precautionary statements P305+P351+P338

Indole-3-carbinol Price More Price(8)

Brand: Sigma-Aldrich(India)
Product number: I7256
Product name : Indole-3-carbinol
Purity:
Packaging: 1G
Price: ₹3095.95
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: I7256
Product name : Indole-3-carbinol
Purity:
Packaging: 5G
Price: ₹7480.08
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: I7256
Product name : Indole-3-carbinol
Purity:
Packaging: 25G
Price: ₹17514.85
Updated: 2022/06/14
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Brand: TCI Chemicals (India)
Product number: I0496
Product name : 3-Indolemethanol
Purity:
Packaging: 5G
Price: ₹4600
Updated: 2022/05/26
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Brand: TCI Chemicals (India)
Product number: I0496
Product name : 3-Indolemethanol
Purity:
Packaging: 25G
Price: ₹19500
Updated: 2022/05/26
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Indole-3-carbinol Chemical Properties,Usage,Production

Chemical Properties Indole-3-carbinol is an off-white powder. It is soluble in organic solvents such as benzene, ethanol, DMSO, and dimethyl formamide (DMF), which should be purged with an inert gas. The solubility of Indole-3-carbinol in ethanol and DMF is approximately 10 mg/ml and approximately 3 mg/ml in DMSO. Indole-3-carbinol is an unstable compound that undergoes rapid oligomerization in acid pH environments, like the stomach.
Occurrence Indole-3-carbinol is produced by members of the family Cruciferae, and particularly members of the genus Brassica (e.g., cabbage, radishes, cauliflower, broccoli, Brussels sprouts, and daikon).
Uses 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.
Preparation Using indole, phosphorus oxychloride and N,N-dimethylformamide as raw materials, indole-3-carbaldehyde was synthesized by Vilsmeier-Haack reaction with a yield of 87.1%.
Definition ChEBI: Indole-3-carbinol is an indolyl alcohol carrying a hydroxymethyl group at position 3. It is a constituent of the cruciferous vegetables and had anticancer activity.
Application Indole-3-carbinol (I3C) is a secondary plant metabolite of 3-methylindole produced in Brassica family vegetables. It is an inhibitor of Amyloid-beta deposition and Inhibits cancinogenesis at the initiation stage. Indole-3-carbinol is used in cancer prevention, specifically for breast, cervical and colon cancers. It has also been widely used to address lupus.
Synthesis Reference(s) Canadian Journal of Chemistry, 31, p. 775, 1953 DOI: 10.1139/v53-106
The Journal of Organic Chemistry, 61, p. 1493, 1996 DOI: 10.1021/jo951219c
General Description Indole-3-carbinol is a novel secondary plant metabolite produced in cruciferous vegetables, such as cabbage, cauliflower and brussels sprouts.
Biochem/physiol Actions 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.
Anticancer Research I3C is a bioactive compound majorly found in Brassica vegetables including broccoli,cauliflower, and collard greens. I3C and its derivative diindolylmethane (DIM)have been investigated for cancer prevention and treatment of breast, prostate, andovarian cancers. I3C partially modulates the tyrosine kinase/PI3K/Akt signalingpathway which leads to the prevention of lung adenocarcinoma which is induced byusing tobacco carcinogen in A/J mice. DIM transduces signaling via aryl hydrocarbon(Ah) receptor, NF-κB/Wnt/Akt/mTOR signaling pathways, cell cycle arrest,modulated cytochrome P450 enzymes, and altered angiogenetic and invasive,metastatic, and epigenetic behavior of cancer cells. Combination of DIM and I3Cinduces Nrf2-mediated phase II drug metabolizing genes (GSTm2, UGT1A1, andNQO1) and antioxidant genes (HO-1, SOD-1) (Weng et al. 2008; 2012).