DL-ALPHA-LIPOIC ACID (C005B-006491)

Application

(±)-α-Lipoic acid has been used in in vitro lipoylation studies and in the pyruvate dehydrogenase complex (PDC)-pyruvate dehydrogenase kinase (PDHK) functional assay. It has also been used to investigate its antioxidative effect on developing cerebellum of rats exposed to arsenic during postnatal period.

Biochem/physiol Actions

(±)-α-Lipoic acid exhibits direct free radical scavenging property and reduces the increased oxidative stress. In addition, it might also exhibit prooxidant activity. α-Lipoic acid functions as an important prosthetic group in α-keto acid dehydrogenase complexes of the mitochondria. It acts as a potential therapeutic for diabetic patients with distal symmetric polyneuropathy (DSP). α-Lipoic acid is also used in the treatment of energy-impaired and redox unbalanced diseases.

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.

Other Notes

Review

Molecular Weight: 206.33. Empirical Formula: C₈H₁₄O₂S₂. Quality Level: 200. Assay: ≥. 98.0% (HPLC), ≥. 98.0%. form: solid. ign. residue: ≤. 0.1%. loss: ≤. 0.2% loss on drying. mp: 60-62 . °C. storage temp.: 2-8°C. 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). Pictograms: GHS07,GHS09. Signal Word: Warning. Hazard Statements: H302 - H315 - H317 - H319 - H411. Precautionary Statements: 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 Code: 11 - Combustible Solids. WGK: WGK 2. Flash Point(F): Not applicable. Flash Point(C): Not applicable. Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves.