Indole-3-carbinol
[CAS# 700-06-1]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Indoles
• Name: Indole-3-carbinol
• Synonyms: 3-Hydroxymethylindole; 3-Indolemethanol; Indole-3-methanol
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.18
• CAS Registry Number: 700-06-1
• EC Number: 211-836-2
• SMILES: C1=CC=C2C(=C1)C(=CN2)CO

Properties

• Melting point: 96-99 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Indole-3-carbinol (I3C) was first discovered in the 1960s when researchers were studying the chemical composition of cruciferous vegetables such as broccoli, cabbage, and Brussels sprouts. The compound comes from the breakdown of glucosinolates, known as viniferin, found in these vegetables. I3C has received attention from the scientific community for its potential health benefits, especially in cancer prevention and hormone regulation.

One of the most studied applications of I3C is its potential in cancer prevention. Studies have shown that I3C affects estrogen metabolism, promoting the formation of less potent estrogen metabolites, thereby reducing the risk of hormone-related cancers such as breast and prostate cancer. Studies have shown that I3C can act as a chemopreventive agent by inducing the production of enzymes that detoxify carcinogens and inhibit the growth of cancer cells.

I3C plays a role in hormone regulation, specifically in regulating estrogen activity. It promotes the balance of estrogen metabolites, which can help prevent estrogen-related diseases and conditions. This property has led to its use in dietary supplements designed to support hormonal health and reduce symptoms associated with estrogen dominance.

In addition to its cancer-preventing properties, I3C is also known for its role in supporting the body's detoxification process. It stimulates the production of Phase II detox enzymes, which help break down and eliminate toxins from the body. This detoxification support aids overall health and can help reduce the risk of various diseases.

I3C is often included in dietary supplements for health promotion and disease prevention. These supplements are often marketed for their potential to support hormonal balance, enhance detoxification, and provide protective effects against certain types of cancer.

Ongoing research continues to explore the therapeutic potential of I3C in a variety of health conditions. Research is investigating its effects on metabolic disorders, autoimmune diseases, and other health problems, with the goal of expanding its use in clinical settings.

References

2010. Chemopreventive Properties of Indole-3-Carbinol, Diindolylmethane and Other Constituents of Cardamom Against Carcinogenesis. Recent Patents on Food, Nutrition & Agriculture, 2(2).
DOI: 10.2174/1876142911002020166

2005. Indole-3-carbinol suppresses NF-kappaB and IkappaBalpha kinase activation, causing inhibition of expression of NF-kappaB-regulated antiapoptotic and metastatic gene products and enhancement of apoptosis in myeloid and leukemia cells. Blood, 106(2).
DOI: 10.1182/blood-2004-12-4589

1987. Structure—activity relationships of dietary indoles: A proposed mechanism of action as modifiers of xenobiotic metabolism. Journal of Toxicology and Environmental Health, 20(1-2).
DOI: 10.1080/15287398709531021