T5625

(±)-α-Lipoic acid

synthetic, ≥99% (titration), powder

• Synonym(s): (±)-1,2-Dithiolane-3-pentanoic acid, 6,8-Dithiooctanoic acid, DL-α-Lipoic acid, DL-6,8-Thioctic acid, Lip(S₂)
• Empirical Formula (Hill Notation): C₈H₁₄O₂S₂
• CAS Number: 1077-28-7
• Molecular Weight: 206.33
• Beilstein/REAXYS Number: 81853
• EC Number: 214-071-2
• MDL number: MFCD00005474
• UNSPSC Code: 12352106
• PubChem Substance ID: 57654679
• NACRES: NA.77

Properties

• biological source: synthetic
• Quality Level: 200
• description: Oxidized form
• assay: ≥99% (titration)
• form: powder
• solubility: ethanol: soluble 50 mg/mL
• SMILES string: OC(=O)CCCCC1CCSS1
• InChI: 1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)
• InChI key: AGBQKNBQESQNJD-UHFFFAOYSA-N
• Gene Information: human ... ACHE(43), BCHE(590) ; rat ... Adra1a(29412), Adra1b(24173), Adra1d(29413)

Description

Application

α-LA can reinstate endothelial activities and alleviate oxidative stress in high-fat fed diabetic rats⁴. It has also been used to analyze ROS production in astrocytes⁵.

Biochem/physiol Actions

Antioxidant and coenzyme needed for the activity of enzyme complexes such as pyruvate dehydrogenase and glycine decarboxylase.

Antioxidant and coenzyme needed for the activity of enzyme complexes such as those of pyruvate dehydrogenase and glycine decarboxylase. Exogenous thioctic acid is reduced intracellularly by two or more enzymes. The reduced form then influences a number of cell processes by direct radical scavenging, recycling of other antioxidants, increasing glutathione synthesis, and modulating transcription factor activity particularly that of NF-κB. Decreases the phagocytosis of myelin by macrophages.

Preparation Note

(±)-α-Lipoic acid (α-LA) is soluble in ethanol at 50 mg/ml

Safety Information

• pictograms: GHS07,GHS09
• signalword: Warning
• hcodes: H302,H315,H317,H319,H411
• pcodes: P261 - P273 - P280 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves