3,3'-Diindolylmethane
[CAS# 1968-05-4]

Identification

• Classification: Biochemical >> Inhibitor >> Endocrinology & hormones >> Androgen receptor agonist
• Name: 3,3'-Diindolylmethane
• Synonyms: 3-(1H-indol-3-ylmethyl)-1H-indole
• Molecular Formula: C₁₇H₁₄N₂
• Molecular Weight: 246.31
• CAS Registry Number: 1968-05-4
• EC Number: 606-355-3
• SMILES: C1=CC=C2C(=C1)C(=CN2)CC3=CNC4=CC=CC=C43

Properties

• Solubility: 50 mM (DMSO 25 °C)
• Melting point: 167 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335-H413
• Safety Statements: P261-P264-P264+P265-P271-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

3,3'-Diindolylmethane (DIM) is a bioactive compound derived from the digestion of indole-3-carbinol and found in cruciferous vegetables such as broccoli and Brussels sprouts. DIM, with the chemical formula C₁₆H₁₁N₃, has attracted attention for its potential health benefits and various applications in medicine and nutrition.

DIM was first discovered in the early 1990s during research on the health benefits of cruciferous vegetables. Researchers were interested in the bioactive compounds in these vegetables and their effects on human health. DIM is an important metabolite of indole-3-carbinol (I3C) that is converted to DIM in the acidic environment of the stomach. The discovery of DIM's bioactivity has led to further research into its potential therapeutic properties and applications.

DIM can be synthesized in the laboratory via a condensation reaction of indole-3-carbinol. The synthesis typically involves the preparation of indole-3-carbinol, which can be derived from cruciferous vegetables or synthesized. Indole-3-carbinol is then condensed under acidic conditions to form DIM. This method ensures the production of pure DIM suitable for research and therapeutic applications.

DIM has been extensively studied for its potential health benefits, especially its role in cancer prevention and treatment. It is thought to have anti-cancer properties that can affect estrogen metabolism and reduce the risk of hormone-related cancers such as breast, prostate, and ovarian cancers. DIM may act as a modulator of estrogen metabolism, promoting the formation of less active estrogen metabolites, thereby reducing cancer risk.

DIM is well known for its potential to balance hormone levels, especially estrogen. By affecting estrogen metabolism, DIM can alleviate symptoms associated with hormone imbalances, such as those experienced during menopause or menstruation. It is sometimes used as a dietary supplement to support hormone health and manage symptoms associated with estrogen dominance.

DIM shows promise in reducing inflammation, a key factor in many chronic diseases. Its anti-inflammatory effects are attributed to its ability to modulate immune responses and reduce oxidative stress. This makes DIM a potential candidate for supporting overall health and managing inflammatory conditions.

In dermatology, DIM is being explored for its potential benefits in treating skin conditions such as acne and psoriasis. Its anti-inflammatory and anti-androgenic properties may help reduce acne lesions and improve skin health by regulating sebum production and reducing inflammation.

DIM is often sold as a dietary supplement with potential health benefits (including hormone balance, cancer prevention, and overall well-being). Its inclusion in supplements is based on its biological activity and research results indicating its health benefits.

References

2024. Gene-Nutrient Interaction and Cancer Prevention. *Handbook of Oncobiology: From Basic to Clinical Sciences*.
DOI: 10.1007/978-981-99-6263-1_30

2024. Anti-proliferative effect of leaf phytochemicals of soursop (Annona muricata L.) against human osteosarcoma in vitro. *Chemical Papers*.
DOI: 10.1007/s11696-024-03349-x

2024. Indole-3-carbinol and its main derivative 3,3′-diindolylmethane: Regulatory roles and therapeutic potential in liver diseases. *Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie*.
DOI: 10.1016/j.biopha.2024.117525