T1395

(±)-α-Lipoic acid

suitable for cell culture, BioReagent, ≥99%

• Synonyme(s) : Thioctic acid, (±)-1,2-Dithiolane-3-pentanoic acid, 6,8-Dithiooctanoic acid, DL-α-Lipoic acid, DL-6,8-Thioctic acid, Lip(S₂)
• Formule empirique (notation de Hill): C₈H₁₄O₂S₂
• Numéro CAS: 1077-28-7
• Poids moléculaire : 206.33
• Numéro Beilstein : 81853
• Numéro CE : 214-071-2
• Numéro MDL: MFCD00005474
• Code UNSPSC : 12352207
• ID de substance PubChem : 24899963
• Nomenclature NACRES : NA.71

Propriétés

• Gamme de produits: BioReagent
• Pureté: ≥99%
• Technique(s): cell culture | mammalian: suitable
• Solubilité: ethanol: 50 mg/mL
• Chaîne SMILES: 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)
• Clé InChI: AGBQKNBQESQNJD-UHFFFAOYSA-N
• Informations sur le gène: human ... ACHE(43) , BCHE(590) ; rat ... Adra1a(29412) , Adra1b(24173) , Adra1d(29413)

Description

Description générale

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. LA improves mitochondrial function and plays a key role in mitochondrial energy metabolism.

Application

Lipoic acid has been used:

• for induction of eryptosis in erythrocytes
• as a constituent in NS21 media for neuronal cultures
• 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
• to elucidate its effect on paraquat poisoning in lungs

Actions biochimiques/physiologiques

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.

Autres remarques

Oxidized form

Informations sur la sécurité

• Pictogrammes: GHS07,GHS09
• Mention d'avertissement: Warning
• Mentions de danger: H302,H315,H317,H319,H411
• Conseils de prudence: P261 - P273 - P280 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• Classification des risques: Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1
• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 2
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: dust mask type N95 (US), Eyeshields, Gloves