ChemDB: Dimethyl Sulfoxide (DMSO)

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Physical Properties

  • Molecular Formula: C₂H₆OS
  • Molecular Weight: 78.13 g/mol
  • Appearance: Colorless, hygroscopic liquid (may appear slightly yellow if impure)
  • Odor: Odorless (pure), but metabolized compounds can produce a garlic-like taste/smell
  • Boiling Point: ~189°C (372.2°F)
  • Melting Point: ~18.5°C (65.3°F)
  • Density: 1.1004 g/cm³ at 20°C
  • Refractive Index: 1.479 (20°C)
  • Viscosity: 1.996 cP at 20°C
  • Surface Tension: 43.54 mN/m at 20°C
  • Dielectric Constant: ~47 (highly polar)
  • Flash Point: 95°C (203°F) (closed cup)
  • Autoignition Temperature: 215°C (419°F)
  • Vapor Pressure: 0.42 mmHg at 20°C
  • Heat of Vaporization: 52.9 kJ/mol
  • Miscibility:
    • Fully miscible with water, alcohols, acetone, ether, benzene, chloroform
    • Immiscible with paraffins (e.g., hexane, mineral oil)
  • Solvent Properties:
    • Excellent polar aprotic solvent
    • Dissolves polar & nonpolar compounds (e.g., salts, polymers, drugs)
    • Penetrates biological membranes easily 

Chemical Properties

  • Structure: Sulfoxide functional group (S=O) with two methyl groups
  • Reactivity:
    • Nucleophilic at oxygen, electrophilic at sulfur
    • Can act as a ligand in coordination chemistry
  • Redox Reactions:
    • Can be reduced to dimethyl sulfide (DMS, (CH₃)₂S)
    • Oxidized to dimethyl sulfone (DMSO₂, (CH₃)₂SO₂)
  • Hydrogen Bonding: Strong H-bond acceptor (but poor donor)
  • Stability:
    • Stable under normal conditions
    • Decomposes at high temps (>189°C) → releases SO₂, CH₄, COS
    • Reacts violently with strong oxidizers (e.g., H₂O₂, HNO₃, perchlorates)
    • Forms explosive mixtures with metal perchlorates

Biological & Pharmacological Properties

  • Cell Permeability:
    • Rapidly penetrates skin, membranes, blood-brain barrier
    • Used as a transdermal drug delivery enhancer
  • Anti-inflammatory & Analgesic Effects:
    • Used in pain relief (e.g., arthritis, sports injuries)
    • May reduce swelling & oxidative stress
  • Cryoprotectant: Preserves cells, tissues, organs in freezing (e.g., stem cells, embryos)
  • Radical Scavenger: Reacts with hydroxyl radicals (•OH) → forms dimethyl sulfone
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