T1395

(±)-α-Lipoic acid

BioReagent, suitable for cell culture, ≥99%

• Synonym(s): Thioctic acid, (±)-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: 81853
• EC Number: 214-071-2
• MDL number: MFCD00005474
• UNSPSC Code: 12352207
• PubChem Substance ID: 24899963
• NACRES: NA.71

Properties

• product line: BioReagent
• Quality Level: 200
• Assay: ≥99%
• technique(s): cell culture | mammalian: suitable
• solubility: ethanol: 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

General description

α-Lipoic acid (LA), a nutritional component found in vegetables and meat, has both antioxidant and oxidant properties. LA exerts therapeutic potential to many diseases like liver cirrhosis, heavy metal poisoning, and diabetic polyneuropathy. LA exerts apoptotic potential in cancer cells either by oxidative stress related pathway or by activation of caspases.[1] LA improves mitochondrial function and plays a key role in mitochondrial energy metabolism.[2]

Application

Lipoic acid has been used:

• for induction of eryptosis in erythrocytes[1]
• as a constituent in NS21 media for neuronal cultures[3]
• to evaluate its effect on liver energy metabolism by high performance liquid chromatography (HPLC) and assessing mitochondrial function by mitochondrial gene expression studies in lipopolysaccharide (LPS) pre-treated mice[2]
• to elucidate its effect on paraquat poisoning in lungs[4]

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.

Other Notes

Oxidized form

Safety Information

• 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