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Lipoic acid ( alpha-lipoic acid ) (1)
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Description
Lipoic Acid
Other Names: α-Lipoic acid, Alpha lipoic acid, Thioctic acid, 6,8-Dithiooctanoic acid, (R)-5-(1,2-Dithiolan-3-yl)pentanoic acid
CAS Number: 1077-28-7
Sum Formula: C₈H₁₄O₂S₂
Molar Mass: 206.32 g/mol
Appearance: Pale yellow crystalline powder
Lipoic acid is an organosulfur compound derived from octanoic acid. It features a five-membered 1,2-dithiolane ring and a carboxylic acid tail, enabling redox activity. It is widely used in redox chemistry, surface science, and coordination chemistry due to its strong metal-chelating and thiol-reactive properties.
Chemical and Physical Properties
Density: ~1.23 g/cm³ (estimated)
Melting Point: 60–62°C
Boiling Point: Decomposes before boiling
Solubility in Water: Slightly soluble
Solubility in Other Solvents: Soluble in ethanol, methanol, acetone, and dimethyl sulfoxide (DMSO); practically insoluble in nonpolar solvents
Odor: Slight sulfur-like odor
Applications
Redox Chemistry: Used in systems requiring thiol/disulfide-based redox cycling.
Surface Functionalization: Applied to modify gold and metal oxide surfaces through thiol binding.
Coordination Chemistry: Serves as a ligand in metal complex synthesis involving soft metal centers.
Polymer and Material Science: Incorporated into responsive or antioxidant-containing polymer systems.
Organic Synthesis: Employed as a precursor for dithiol-containing compounds and as a reducing agent in mild systems.
Safety
Signal Word: Warning
H302 (93.5%): Harmful if swallowed [Warning Acute toxicity, oral]
H315 (48.6%): Causes skin irritation [Warning Skin corrosion/irritation]
H317 (46.5%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H319 (47%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H411 (46.5%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
P261, P264, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P391, and P501
Handling and Storage
Storage Conditions: Store in a tightly sealed container in a cool, dry, and dark place. Protect from heat, moisture, and strong oxidizing agents.
Handling Precautions: Minimize exposure to air and light. Handle under inert atmosphere for long-term stability. Use proper PPE and standard laboratory practices.