DIM (Diindolylmethane)

Diindolylmethane (DIM) is a naturally occurring indole derivative produced during the acidic digestion of indole‑3‑carbinol, a compound found in cruciferous vegetables (e.g., broccoli, cabbage). In the body, DIM is studied primarily for its ability to modulate estrogen metabolism and exert anti‑oxidant, anti‑inflammatory, and anti‑cancer activities, making it a popular nutraceutical for hormone‑related health support.

• Diindolylmethane (DIM) has the molecular formula C₁₇H₂₀N₂ and a molecular weight of 244.35 g/mol.
• IUPAC name: 3,3′‑Bis(1H-indol‑3‑yl)propane.
• The structure consists of two indole rings linked through a central methane (CH₂) bridge, giving it a planar, aromatic configuration that facilitates interaction with the AhR ligand‑binding domain.
• DIM is lipophilic (log P ≈ 3.2), poorly soluble in water but readily soluble in ethanol, DMSO, and oil‑based carriers, which influences formulation choices (e.g., enteric‑coated capsules).
• Its stability is pH‑dependent; it degrades under alkaline conditions but is stable in acidic gastric environments, facilitating oral absorption.

• DIM is primarily derived from indole‑3‑carbinol found in cruciferous vegetables (broccoli, Brussels sprouts, kale).
• Industrial production uses either:
  • (a) extraction of indole‑3‑carbinol from vegetable extracts followed by acid‑catalyzed condensation to form DIM, or
  • (b) total chemical synthesis from indole precursors via a Friedel-Crafts alkylation.
• High‑quality supplements employ “phytosynthesized” DIM from organic‑grown crucifers, guaranteeing low pesticide residues.
• Good Manufacturing Practice (GMP)‑certified manufacturers must verify purity (> 98 %) via HPLC and confirm the absence of heavy metals, pesticides, and residual solvents.
• For clinical use, a Certificate of Analysis (COA) confirming identity, purity, and absence of contaminants is essential.